Vacation Rentals By Owner In Siesta Key, FL

Discover Key Lime Retreat, an end-unit condo perfectly situated in the heart of Siesta Key. This delightful getaway combines comfort with modern style, ideal for families or a group of friends. Tucked away in a tropical garden setting, you'll enjoy access to a community pool, perfect for a refreshing dip. Everything you need is just a short walk away, from the pristine sands of Siesta Key Beach to vibrant shopping and delicious dining options. Inside, you'll find a thoughtfully designed space. The luxurious primary bedroom features a king-sized bed, while the guest bedroom is equipped with a twin bed plus a bunk bed, comfortably accommodating everyone. A newly updated bathroom offers a fresh space for relaxation, and the brand-new, fully equipped kitchen boasts modern appliances for all your culinary adventures. Nestled in a quiet building of just six units, Key Lime Retreat offers a serene escape. Step out onto your private front patio overlooking the garden and pool, a tranquil spot to savor your morning coffee or read a good book during the evening sunset. Whether you're here to explore or simply unwind, Key Lime Retreat promises a memorable and peaceful stay.brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: To adhere to HOA guidelines, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

Keylime Retreat | End-Unit Condo, Walk to SK Beach & Village, Pool Access

Siesta Key, Florida, United States

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Bath

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$529.21

Your Siesta Key Dream Starts Here in a Prime Location! Discover your perfect vacation getaway in this charming three-bedroom home with a private pool, ideally situated in a prime spot just a quick six-house stroll from the world-famous Siesta Key Beach! Enjoy the best of Siesta Key with effortless access to both relaxation and recreation. Spend your days soaking up the Florida sun, whether lounging by your own sparkling private pool or sinking your toes into the powdery white sands of Siesta Key Beach, just moments away. Unwind in the welcoming living and dining areas. The fully-equipped kitchen makes meal prep a breeze, allowing you to whip up everything from beach snacks to gourmet dinners. When it's time to rest, you'll find three cozy bedrooms, each offering a peaceful sanctuary with comfortable beds and plenty of space to unpack and settle in. And the convenience of this prime location continues with a short walk to the vibrant Siesta Key Village, offering a delightful array of shops, restaurants, and entertainment. Experience the best of both worlds: tranquil poolside living in a fantastic location with easy access to the beach and village excitement!brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: For the comfort of all our guests, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

Blue Wave | Prime Siesta Key - Walk to Beach & Village, Plus Private Pool

Siesta Key, Florida, United States

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Bath

Sleeps

$460.37

Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kids downstairs and a relaxing haven for adults upstairs. No need to fight over the king-size bed, as this home boasts two luxurious king-size bedrooms! Both offer comfortable retreats and easy access to your private pool, perfect for a refreshing dip anytime. The third bedroom features a trundle bed that comfortably sleeps two. Outside, the private pool area awaits with lounge chairs for sunbathing, an outdoor shower, and a delightful area to grill and enjoy alfresco dining at the table for six. Just moments away, the vibrant energy of Siesta Key Village, with its diverse culinary scene and local shops, offers endless opportunities for exploration. Surf's Up provides the ideal launchpad for experiencing all that Siesta Key has to offer, with plenty of room to relax and recharge in between adventures. Perfect for families seeking sun, relaxation, and easy access to Siesta Key Beach & Village. Book your unforgettable getaway now! brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: We're delighted to welcome your furry family members! This property is pet-friendly, and a non-refundable pet fee (per pet) will be applied after booking and must be paid prior to check-in. Please feel free to inquire about the specific pet policy applicable to your reservation.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

Surf's Up | Walk to Siesta Key Beach & Village, Private Pool, Dog Friendly

Siesta Key, Florida, United States

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Bath

Sleeps

$232.59

Experience the ultimate beach getaway at Carefree Coconut, a charming second-floor corner unit located in the heart of Siesta Key's welcoming Vista Hermosa community. True to its Spanish name, Beautiful View, this community offers a delightful escape, blending old Florida charm with modern comforts. Step inside to discover a bright and airy space, filled with natural light, featuring a screened balcony with comfortable seating and a remodeled kitchen ideal for entertaining or for the chef in your family. The property includes a primary bedroom with a comfortable King-sized bed and a guest bedroom with a Double bed and a Twin bed with a trundle, ensuring restful nights. The Vista Hermosa community itself provides fantastic resort-style amenities, including a refreshing heated pool, fun shuffleboard courts, a convenient gas grill with picnic tables, and a clubhouse featuring a kitchen – perfect for socializing and making new memories! Your prime location means you're just moments from the lively South Village, a hub of locally-owned restaurants, charming cafes, vibrant bars, and unique boutiques. A leisurely ten-minute walk brings you to Siesta Key’s stunning Crescent Beach, famous for collecting seashells and those world-renowned Gulf sunsets. For an unforgettable underwater experience, the unique landmark Point of Rocks is also nearby, a snorkeler's paradise teeming with tropical fish and vibrant coral reefs! For larger groups, consider booking unit 308C, also managed by Ascendia Group, which can accommodate an additional 4 guests, allowing your whole family to enjoy this incredible destination together. Come discover why Carefree Coconut is the perfect spot for your next Siesta Key escape!brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: To adhere to HOA guidelines, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

Carefree Coconut | Walk to SK South Village w/ Live Music & Restaurants

Siesta Key, Florida, United States

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Bath

Sleeps

$221.97

Book now and enjoy this newly renovated Light & Bright condo with premium features. Everything in this condo came out of the box recently plus all new flooring....new & fresh! Book this ideally located top floor condo in a premium complex now to enjoy Siesta Key has to offer. Midnight Cove II is ideally located near the South bridge for convenience, next to the South Village with shops and restaurants and features gated private access to the world-famous Siesta Key beach. You will enjoy the on-site office and professional management with direct owner contact in the event you need anything else. Book now and let us welcome you to Fun & Sun!brbrThis unit features a great floor plan and renovation. The unit is engrossed in sunlight from the wall of sliders facing the boat basin and ICW. The modern design is classic & comfortable. Enjoy the relaxing master suite with queen bed, guest suite has 2 twins and large sofa is a premium queen pull-out. There is a large flat screen in the living area, in the master suite and another in the guest bedroom (3 total). Everything is new - appliances, glasses, dishes, towels, bed sheets, mattresses, couches, tables, chairs....EVERYTHING was new from recent renovation. Just because you are away from home, it does not mean you need to be without! Stay with us and let us pamper you.brbrAs a complex, Midnight Cove II is the best on the island. From the moment you cross onto the island, you will love the convenient location. You will be close enough to shops, dining and bars...but far enough away to enjoy the peace & quiet. With gated beach access and a push-button-crosswalk available on demand, you can immerse yourself in all the beach has to offer. If you have time, you will fall in love with the open spaces of Midnight Cove II - the vast amount of pavers welcomes you and your guests to ample parking and room to roam...a premium on Siesta Key. The on-site security and management ensures that the heated pool, tennis courts, workout area, BBQ station and more is in mint condition. brbrWe have tried to anticipate all of your vacation needs - we look forward to welcoming you!

Renovated condo with premium features on Siesta Key

Siesta Key, Florida, United States

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Bath

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$236.17

Here's your family's perfect opportunity to enjoy Siesta Key, the country's best beach, within the coastal, rustic elegance of one of the best beach-side villas on Siesta Key--Beachaven #6. brbrAbout the Condo:brImagine, after your family experiences the refreshing azure waters of the Gulf and sugary sand beaches of Beachaven's private beach and pool, you can catch your breath and relax among the newly remodeled comfort of your own stylish beach house. Completely renovated in 2016 in a charming coastal-industrial style, Beachaven #6 stylishly sleeps a family/group of four, and features all new appliances and furnishings, a washer & dryer at the unit, two large flatscreen TVs, high-speed WiFi, high-top dining for four, breakfast bar with seating for four, a spacious stand-up shower, two twin beds, leather pull-out sofa, and covered parking for one car. brbrAbout Beachaven:brBeachaven is a rare gem here on Siesta Key. Whereas most condominiums on Siesta Key are traditional high-rise structures with hundreds of units and complicated grounds, Beachaven is a small, quaint and very charming beach-side community that makes guests feel relaxed, secure, and carefree. The complex is laid out in a simple linear fashion, with a straight shot, short walk to the beach; and because the complex is small, our beach is always un-crowded and feels like your private piece of paradise. brbrBeachaven Fun Fact #1:brBeachaven boasts one of only a handful of pools on Siesta Key that is actually nestled in the sand, only a few hundred feet from the ocean waters. This means your family can easily step from the pool to the beach and from the beach to the beach with zero hassles and zero cares. brbrBeachaven Fun Fact #2:brBeachaven boasts a clubhouse, also on the beach with full-service kitchen, seating, and bathrooms, so your family can enjoy lunch, or a sunset celebration, overlooking the pool and sands of Siesta Key.brbrBeachaven Fun Fact #3brBecause Beachaven is a very small complex with less than a hundred units, the beach is always very quiet and very private. As you stand at the pool and look left and right you will see hundreds of beach-goers, however on your private beach you will see very few. This exclusivity is especially valuable during the daily sunset celebrations when your family enjoys the twilight hours and the feeling like the sun is performing a private show just for you. brbrBeachaven Fun Fact #4brYou already know that Beachaven is on Siesta Key, voted the best beach in America, but did you also know that Beachaven is perfectly--and centrally--located in the heart of Siesta Key, just one south of the North Village and one mile north of the South Village Plus within less than a hundred steps from Beachaven Unit 6, you can hop on any number of free trolleys and shuttles to both Villages. brbrBeachaven Fun Fact #5brOnce again, because Beachaven is a single-story, linear designed complex, with a beautifully manicured landscaped mall in between, your family can enjoy the grounds safely and securely all within easy site of your villa. brbrBeachaven Fun Fact #6brBeachaven also has a soothing and serene reflection pool, which is located at the East end of the complex and within steps from Villa #6. brbrBeachaven Fun Fact #7brBeachaven is so simple and relaxing that guests aren't the only wildlife who like to relax on the grounds; you will also find a number of feathered friends on property, including vibrant wild parrots, egrets, cranes, and, of course, a host of colorful seagulls. brbr br

Villa

Newly renovated. Gulf-side condo. Your own private beach directly on Siesta Key.

Siesta Key, Florida, United States

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Bath

Sleeps

$302.68

This property is a stunning, tropically landscaped, fully updated and renovated home located on Siesta Key. It boasts spacious vaulted ceilings, tile floors, new furnishings, and stylish decor throughout. The kitchen is equipped with stainless steel appliances, granite countertops, and an eat-at bar. The living room features a 60-inch flat screen HD TV with over 200 channels. Most rooms offer outdoor views and have access to the pool area. This property includes three bedrooms, comfortably accommodating six adults. Additionally, it offers a beautiful outdoor, screened-in, full-size pool with a propane grill and outdoor furniture, overlooking the canal. The house underwent significant renovations in 2014, and the pool area was completely updated in June 2024. Situated in a quiet, secluded neighborhood just half a mile from public beach access, this property also offers free ride services and bicycles, eliminating the need for a rental car. It’s an absolutely beautiful home, perfect for relaxation!

Siesta Key family-friendly house with large pool

Siesta Key, Florida, United States

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Bath

Sleeps

$271.64

Pinkie Flamingo Welcomes You to The Tortuga #105B!brKing / Kingbr30 Night MinimumbrbrA rare find indeed! Come prepared to leave impressed.This rarely available courtyard unit in the coveted B Building of The Gulf-front Tortuga Beach Resort is new to the vacation rental market and will soon be on your favorites list. It's the ideal get away for Seasonal snowbirds and Summer guests alike. Both the King master and Queen guest bedrooms are en-suite with plenty of privacy and space. A bright and beautifully tiled living area with Gulf and garden views provides many options to enjoy, relax and entertain. Open and airy, The Turtle's Nest is comfortably furnished and decorated in natural earth tones. Panoramic windows highlight the meticulously groomed and maintained complex below. With every amenity you expect an island resort to provide, The Tortuga Beach Resort features a spacious, remodeled clubhouse to gather and watch sports, socialize and enjoy holiday parties; a heated indoor/outdoor pool and private access to the world-famous beaches of Siesta Key. Guests enjoy tennis court privileges at Turtle Bay across the street. The Turtle's Nest is within walking distance to several popular restaurants and Siesta Key Village is less than 5 minutes away via car or trolley. The free Siesta Key Breeze Trolley picks up in front of the complex and covers the entire island. Guest may ride to Siesta Key Village, Crescent Beach, Siesta Key Public Beach Pavilion, and everywhere in between.brbrOne month minimum booking is required Nov and/or December. Three-month minimum booking Jan through March. Longer term options and discounts on rentals over 3 months.brContact Pinkie at pinkieflamingo.com for more information!brbrCome To Florida…For The Fun Of ItbrbrAll of Pinkie's Properties Have A Few Things In Commonbr• Must Be 25 To Bookbr• No Smoking br• Cancellation OK 30 Days Prior To Check-Inbr• Sheets & Bath Towels Included…BYO Beach Towelsbr• All Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & Foodbr• Basic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need MorebrbrKeywords: Siesta Key Vacation Rental, Siesta Key Condo Rental, Condo Rental Siesta Key, The Tortuga Resort Siesta Key

The Perfect Snowbird Nest on Siesta Key! Minimum 30-Day Rental

Siesta Key, Florida, United States

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Bath

Sleeps

$458.42

The PropertybrThe best view on Siesta Key is found at the Dreamview Beach Front Condo. Find your romantic getaway at our 1 Bedroom, 1-1/2 Bath suite on the 3rd floor of the Beachfront Suites on Siesta Key, where you are only steps away from digging your toes into the sugary sand of the #1 Beach. The bright and airy space is warm and inviting, featuring comfortable living room furniture, a large fully stocked kitchen, a plush king bed with high-end bedding, and a private balcony for you to enjoy your favorite glass of wine and watch an unforgettable sunset.brbrThe Dreamview Suite is perfect for a romantic getaway, couples, or small families.brbrDog Friendly: brWe do accept dogs up to 50 lbs. There is a pet fee of $35 per dog per night.brbr**Traveling with a larger group Ask about renting multiple units at the Beachfront Suites to accommodate your whole group. br brAmenitiesbrImmediate Beach AccessbrAmazing Views of the Gulf of MexicobrFully Stocked KitchenbrLarge Jacuzzi BathtubbrPrivate BalconybrHD Smart TV'sbrLarge Shared BackyardbrOutdoor FirepitbrPicnic AreabrPropane & Charcoal GrillbrOutdoor GamesbrBoard Gamesbr brPet PolicybrThe Dreamview Condo is Dog-Friendly for 1 Dog of 50lbs or fewer pounds or two dogs with a combined weight of 50 pounds. An additional $100 cleaning pet fee and $500 Refundable Damage Deposit will be applied for guests with pets. Guests with Pets must sign the Pet Waiver.brbrThe Local Areabr.25 Miles to Siesta Key Public Beachbr.5 Miles to Siesta Key Villagebr6 Miles to Downtown SarasotabrbrThe Beach Front SuitesbrThe Beachfront Suites is a stand-alone tri-plex. The building is three stories with each floor as its own unit. The Dreamview Condo is located on the 3rd floor. brbrWhat's provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner. brbr**Minimum Age 25: All Reservations must be booked by and accompanied by an adult who is 25 years of age or older. Valid photo I.D. may be required at the time of booking. br**Your inquiry on our property will be responded directly to your personal email. Please keep a lookout for our response so we may best serve your requestbrbrCancellation PolicybrBookings canceled at least 30 days before the start of the stay will receive a 100% refund minus Cancellation Fee's ($100 plus 6% Credit Card Processing Fee). Bookings canceled at least 14 days before the start of the stay will receive a 50% refund Minus Cancellation Fee's. Bookings canceled within the 14-day window are non-refundable. brbrReservations of 15 nights or more may be canceled at least 90 days before the start of the stay will receive a 100% refund minus Cancellation Fee's ($100 plus 6% Credit Card Processing Fee). Cancellations within 45 days of the check-in date and are refundable up to 50% minus Cancellation Fee's.brbrShould a refund be issued, a credit to the original credit card in the amount of the reservation minus the cost of the cancellation fees will be issued within 5 to 7 business days.

Romantic 1BR - Siesta Key Beach Sunset View

Siesta Key, Florida, United States

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Bath

Sleeps

$1915.16

Summary:brbrEscape to Oasis on the Key, a stunning villa in the heart of Siesta Key Village. This elegant home offers a private heated pool and is steps away from the beach and vibrant village life. Perfect for families, it comfortably accommodates up to 14 guests, offering a luxurious and convenient vacation experience.brbrbrbrThe Space:brbrThis charming Siesta Key vacation rental home is a unique combination of two units: “Baybreeze” and “Pinacolada” (3200 sq. ft. total). Each unit features a 3BR/2.5BA configuration, each with their very own common space to include a kitchen, dining area, living room and outdoor patio area. When booked together, Coconut Grove offers a private heated pool (when booked separately, the pool is shared between the two units). This home has every amenity you could fathom at an absolutely location in the HEART of Siesta Key Village and just a 4 minute walk to the #1 beach in the USA!brbrbrbrGuest Access:brbrThis charming Siesta Key vacation rental home is a unique combination of two units: “Sea La Vie” and “Endless Summer” (3200 sq. ft. total). Each unit features a 3BR/2.5BA configuration, each with its very own common space to include a kitchen, dining area, living room and outdoor patio area. When booked together, Oasis on the key offers a private heated pool (when booked separately, the pool is shared between the two units). This home has every amenity you could fathom at an absolute location in the HEART of Siesta Key Village and just a 2-minute walk to the #1 beach in the USA! brbrbrbrCoconut Grove can accommodate up to 16 guests with a bedding configuration as follows:brbrbrbrEndless Summer can accommodate up to 8 guests with a bedding configuration as follows:brbrbrbr• Bedroom # 1: King Bed (1) - Sleeps: 2brbr• Bedroom # 2: Queen Bed (1) - Sleeps: 2brbr• Bedroom # 3: Queen Bed (2) - Sleeps: 4brbrbrbrSea La Vie can accommodate up to 8 guests with a bedding configuration as follows:brbrbrbr• Bedroom # 1: King Bed (1) - Sleeps: 2brbr• Bedroom # 2: Queen Bed (1) - Sleeps: 2brbr• Bedroom # 3: Queen Bed (2) - Sleeps: 4brbrbrbrExclusive Amenities Include:brbrbrbr• Private Heated Pool (when rented separately, the pool is shared between both units)brbr• Linens Providedbrbr• Regular Coffee Makersbrbr• Kitchen Essentials Providedbrbr• Flat Screen HDTVs (in every bedroom + each living room)brbr• Beach Towelsbrbr• Beach Caddy (2)brbr• Coolers (2)brbr• Beach Chairsbrbr• Outdoor Lounge Areabrbr• Gas Grillbrbr• Views of Siesta Key Villagebrbr• 2 Minute Walk to Siesta Key Beach (when using beach access #5)brbr• Outdoor Showerbrbr• Washer/Dryer (in unit)brbr• Secure Parking in Lotbrbr• Free WiFIbrbrbrbrbrbrThis property hasbrbrBedroom #1: King Bed (1)brbrBedroom #2: Queen Bed (1)brbrBedroom #3: Queen Bed (2)brbrBedroom #4: King Bed (1)brbrBedroom #5: Queen Bed (1)brbrBedroom #6: Queen Bed (2)brbrbrbrThe Neighborhood:brbrSiesta Key, Florida is very proud of our sand. In fact, we have the “World’s Finest Whitest Sand”. You’ll find beautiful seashells on Siesta’s white sands, and you’ll find the finest beach-front vacation rentals and showcase homes on the Key, too. What else can you find on the sands of Siesta Key brbrbrbrYou are sure to see and hear our wild parrots and the friendly pelicans while you stroll the breathtaking 8-mile long barrier island that is Siesta Key. Siesta Village is famous for its wild parrots up in the swaying palm trees as well as many other shorebirds including terns, plovers, ibis, spoonbills, and storks. Bird watching is one of the favourite activities of residents and visitors alike. The many varieties of wading birds, like the beautiful snowy egret, and the great heron are just a few of the different types on our beaches and in our village. Keep an eye out for our 4 to 5 foot tall Florida Sand Hill Cranes with their bright red heads and distinctive calling sounds. You will often see two walking side by side since they mate for life. Our birds seem to live comfortably among the people of Siesta Key.brbrbrbrGetting Around:brbrGetting around Siesta Key is a breeze! While exploring the Village and beach is easy on foot, you'll find convenient access to various transportation options. Public transportation, including local buses, is available for trips to Sarasota and surrounding areas. For those arriving by air, Sarasota Bradenton International Airport (SRQ) is a short drive away, approximately 20 minutes depending on traffic. Ample parking is available at the property, ensuring a hassle-free stay for you and your guests. Explore the beauty of Siesta Key and the wider region with ease, knowing you have convenient travel options at your fingertips.brbrbrbrOther Things to Note:brbrAttractions brbrBay brbrCoin LaundrybrbrHealth Beauty SpabrbrMarinabrbrMuseumsbrbrParksbrbrWater ParksbrbrWinery ToursbrbrZoobrbrbrbrEntertainmentbrbrSatellite / CablebrbrTelevisionbrbrFeaturesbrbrAir ConditioningbrbrCentral HeatbrbrClothes DryerbrbrHair DryerbrbrHeatingbrbrInternet - Hi SpeedbrbrInternet - WirelessbrbrIron and BoardbrbrLinens ProvidedbrbrLiving RoombrbrParkingbrbrTowels ProvidedbrbrWashing MachinebrbrKitchenbrbrCoffee MakerbrbrCookwarebrbrDining AreabrbrDining SpicesbrbrDishes & UtensilsbrbrDishwasherbrbrKitchenbrbrMicrowavebrbrOvenbrbrRefrigeratorbrbrStovebrbrToasterbrbrLeisurebrbrAntiquingbrbrBird WatchingbrbrBoatingbrbrEco TourismbrbrGamblingbrbrOutlet ShoppingbrbrPaddle BoatbrbrShoppingbrbrWater SportsbrbrWildlife ViewingbrbrbrbrLocalbrbrHospitalbrbrLaundromatbrbrLocationbrbrBeachbrbrNear OceanbrbrVillagebrbrOutdoorbrbrDeck/PatiobrbrGas GrillbrbrPoolbrbrHeated PoolbrbrPrivate PoolbrbrSportsbrbrBasketball CourtbrbrBikingbrbrDeep Sea FishingbrbrFishingbrbrFishing BaybrbrFishing FlybrbrFishing SurfbrbrGolf OptionalbrbrGolfingbrbrHikingbrbrJet SkiingbrbrKayakingbrbrParaglidingbrbrParasailingbrbrPier FishingbrbrRoller BladingbrbrSailingbrbrScuba or SnorkelingbrbrSnorkelingbrbrSurfingbrbrSwimmingbrbrWater SkiingbrbrWater TubingbrbrWind SurfingbrbrThemesbrbrFamilybrbrLuxurybrbrbrbrCancellation; Non-Refundable Transaction Fee VRBO BOOKING.COM ONLY In the event of any cancellation,or, or termination, of a booking for any reason whatsoever, the 3.9% transaction processing fee assessed at the time of payment shall be strictly non-refundable. This fee represents payment processing costs incurred and is earned immediately upon receipt of funds. Under no circumstances shall the 3.9% transaction fee be returned, credited, or otherwise reimbursed, including but not limited to cancellations made within any stated refund period, force major events, or cancellations initiated by the Guest. Any applicable refund shall be calculated net of the 3.9% transaction processing fee.brbrbrbrInteraction with Guests:brbrI am available throughout your stay to assist with any questions or needs. You can reach me anytime via the booking platform messaging system. I strive to respond as quickly as possible.brbrbrbrCancellation; Non-Refundable Transaction Fee VRBO BOOKING.COM ONLY In the event of any cancellation,or, or termination, of a booking for any reason whatsoever, the 3.9% transaction processing fee assessed at the time of payment shall be strictly non-refundable. This fee represents payment processing costs incurred and is earned immediately upon receipt of funds. Under no circumstances shall the 3.9% transaction fee be returned, credited, or otherwise reimbursed, including but not limited to cancellations made within any stated refund period, force majeure events, or cancellations initiated by the Guest. Any applicable refund shall be calculated net of the 3.9% transaction processing fee.

Siesta Key Village Heated pool

Siesta Key, Florida, United States

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Bath

Sleeps

$748.94

The Coral Cabanas C & DbrJust 8-steps to path of Siesta Key Beach, world's best beach! 4-minute walk to bars, entertainment, shopping, dining, ice cream and live music of the South Village! Listing includes two side-by-side units including a 1BR and 2BR (total 3BR). Book your getaway now!brbrWhat Guests Lovebr∙ Separate Units – 2 units deliver space and privacy, perfect for large gatheringsbr∙ Beaches – 11-step walk to award winning Siesta Key beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –walk 30-seconds to Siesta Key's best sunsets and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - 4-min walk to the South Village's live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Key West-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrListing includes two side-by-side units including a 1BR and 2BR (total 3BR), one staircase above ground level. The 1BR unit has a large queen bedroom and a queen sleeper in the living room. You can sleep up to 11 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found for sale or rental nearby! brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrSiesta Key is a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Hammocks, Snorkeling, Sunsets

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$774.02

The Coral Cabanas A & BbrJust 8-steps to path of Siesta Key Beach, world's best beach! 4-minute walk to bars, entertainment, shopping, dining, ice cream and live music of the South Village! Listing includes two side-by-side units including a 1BR and 2BR (total 3BR). Book your getaway now!brbrWhat Guests Lovebr∙ Separate Units – 2 units deliver space and privacy, perfect for large gatheringsbr∙ Beaches – 11-step walk to award winning Siesta Key beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –walk 30-seconds to Siesta Key's best sunsets and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - 4-min walk to the South Village's live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Key West-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrListing includes two side-by-side units including a 1BR and 2BR (total 3BR), one staircase above ground level. The 1BR unit has a large queen bedroom and a queen sleeper in the living room. You can sleep up to 11 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found nearby! brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrSiesta Key is a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Hammocks, Snorkeling, Sunsets!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$2522.03

The Coral Cabanas InnbrJust 8-steps to path of Siesta Key Beach, the world's best beach! 100% private 8BR including 5 units. 4-minute walk to bars, entertainment, shopping, dining and live music! Communal lounging, alfresco dining, snorkeling, sunsets, and hammocks. Listing includes two side-by-side units including a 1BR and 2BR (total 3BR). Book your groups Siesta Key vacation rental getaway now!brbrWhat Guests Lovebr∙ Separate Units – 5 units deliver space and privacy, perfect for large gatheringsbr∙ Beaches – 12-step walk to Siesta Key's award winning beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –walk 30-seconds to best sunsets on Siesta Key and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - 4-min walk to South Village and live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Siesta Key-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrListing includes three 2BR and two 1BR units (8BR total). One 2BR unit is ground level, other units are one flight up. The 1BR units have a large queen bedroom and a queen sleeper in the living room. Two of the 2BR units have a large queen BR, a room with two doubles, and a sleeper sofa. The ground floor 2BR unit has two queen bedrooms and a queen sleeper sofa in the living room. The property can sleep up to 31 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found for sale or rental nearby! brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrSiesta Key is a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$366.09

The Coral Cabanas Poor-BoybrJust 8-steps to path of Siesta Key Beach, the world's best beach! 4-minute walk to bars, entertainment, shopping, dining and live music in the South Village! Communal lounging, private patio, alfresco dining, snorkeling, sunsets, and hammocks. This is a budget two-bedroom priced like our one bedroom units. Read the description below, see if it's a fit for you, and book a Siesta Key vacation rental getaway today!brbrWhat Guests Lovebr∙ Beaches – 12-step walk to Siesta Key's award winning beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ The Price – this is a budget 2BR priced like our 1BR units, this listing is direct at the guaranteed lowest costbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Private Patio – this is the only unit on the property with a private patiobr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –walk 30-seconds to Siesta Key's best sunsets and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - 4-min walk to the South Village and live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbrbrProperty TruthsbrThis Siesta Key vacation rental is a budget 2BR accommodation priced like our 1BR units. It has everything our prime units have except sound insulation in the ceiling which, although usually not an issue, might result in noise from above. If you want to experience Siesta Key, less than one minute walk from the best beach on the island but are on a budget and are not sensitive to noise from the ceiling above then the poor boy should be the perfect place for you.brbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Siesta Key-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrThis property is two stories and this unit is one flight up with no one above it or below it. There is a king bedroom, a queen bedroom and a sleeper sofa. You can sleep up to 7 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found nearby! brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Low Price

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$340.83

The Coral CabanasbrJust 8-steps to path of Siesta Key Beach, world's best beach! 4-minute walk to bars, entertainment, shopping, dining, ice cream and live music of the South Village! Communal lounging, alfresco dining, snorkeling, sunsets, and hammocks. Perfect for families and couples looking to relax, explore and repeat. Book your Siesta Key vacation rental getaway direct now!brbrWhat Guests Lovebr∙ Beaches – 11-step walk to award winning Siesta Key beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –walk 30-seconds to Siesta Key's best sunsets and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - 4-min walk to the South Village's live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Key West-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrThis property is two stories and this unit is one flight up with no one above it or below it. There is one large queen bedroom and a queen sleeper in the living room. You can sleep up to 4 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found nearby! brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.

Gertrude's Siesta |1 min walk to Beach Path | Near Dining, Music, Hammocks & Sunsets

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$290.91

The Coral CabanasbrJust 8-steps to path of world's best beach! 4-minute walk to bars, entertainment, shopping, dining and live music! Communal lounging, alfresco dining, snorkeling, sunsets, and hammocks. Perfect for couples looking to relax, explore and repeat. Book your getaway now!brbrWhat Guests Lovebr∙ Beaches – 12-step walk to award winning beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –walk 30-seconds to best sunsets and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Key West-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrThis property is two stories and this unit is one flight up with no one above it or below it. There is one large queen bedroom and a queen sleeper in the living room. You can sleep up to 4 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found nearby! brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude's Siesta | 1 min walk to Beach Path | 4 Min to Dining, Music & Sunsets

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$416.0

The Coral CabanasbrJust 8-steps to path of world's best beach! 4-minute walk to bars, entertainment, shopping, dining and live music! Communal lounging, alfresco dining, snorkeling, sunsets, and hammocks. Perfect for couples looking to relax, explore and repeat. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Beaches – 12-step walk to award winning beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –walk 30-seconds to best sunsets and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbrbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Key West-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrThis property is two stories and this unit is one flight up with no one above it or below it. There is a king bedroom, a bedroom with two double beds and a sleeper sofa. You can sleep up to 7 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only. brbrbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.

Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Hammocks, Snorkeling, Sunsets!

Siesta Key, Florida, United States

2

Bed

1

Bath

8

Sleeps

$409.53

Summary:brbrWelcome to your perfect Florida getaway! brbr- Beautifully remodeled single-family home brbr- 3 spacious bedrooms, 2 modern bathrooms brbr- Private heated pool with sunshelf brbr- Short walk to restaurants, bars, and shops brbr- Local beach just 3 blocks away brbr- Close to Siesta Key Beach, top-rated worldwide brbr- Family-oriented home with quiet hours brbrWelcome to your perfect vacation getaway!brbrbrbrThe Space:brbrWelcome to your perfect Florida getaway! This beautifully remodeled single-family home features 3 spacious bedrooms and 2 modern bathrooms, ideal for families or groups looking to relax in style. Whether you're soaking in the sun on the pool shelf, exploring local hot spots, or relaxing indoors, this home is designed for comfort and fun.brbrbrbrStep outside and enjoy your private 27' x 13' heated pool, set to a comfortable 82 degrees year-round. The pool includes a sunshelf, perfect for lounging in the water with a cocktail or even enjoying dinner alfresco right in the pool! brbrbrbrComfortable Accommodation:brbr- 3 spacious bedroomsbrbr- 2 modern bathroomsbrbr- Family-oriented atmospherebrbrbrbrInterior Feeling:brbr- Beautifully remodeledbrbr- Temperature set to a comfortable 72°Fbrbr- No ceiling fansbrbrbrbrOutdoor Bliss:brbr- Private heated poolbrbr- Sunshelf for loungingbrbr- Short walk to the local beach, just 3 blocks awaybrbrbrbrDelightful Dining:brbr- Over 15 restaurants within walking distancebrbr- 12 bars and boutique shops nearbybrbr- Bike/scooter rentals and wash & fold services availablebrbrbrbrNearby Attractions:brbr- Famous Siesta Key Beach, voted one of the Top 10 Beaches in the Worldbrbr- Local golf courses, cultural sites, and nature trailsbrbrbrbrProfessional Cleaning:brbr- Pool professionally cleaned once a weekbrbr- Pool net provided for conveniencebrbrbrbrImportant Information & House Rules:brbr- No beach chairs, umbrellas, towels, or toys providedbrbr- Primary renter must be at least 25 years oldbrbr- Quiet hours must be respectedbrbr- Treat the home and neighborhood with carebrbrbrbrWelcome to your perfect vacation getaway!brbrbrbrOther Things to Note:brbrHere are the important policies and guidelines to note for your stay:brbrbrbrCheck-in: We facilitate self-check-in, and guests are welcome to check in any time after 4 pmbrbrbrbrCheck-out: We kindly ask that you check out on or before 11:00 AM on your departure date. This allows us enough time to clean and prepare the property for the next guests. No dishwasher available, so we kindly ask that you wash the dishes before checkout.brbrbrbrNo Smoking: Smoking is strictly prohibited inside the house and within any common areas of the complex. Please respect this policy to maintain a clean and smoke-free environment.brbrbrbrNo Parties: The house is intended for quiet and peaceful stays, and hosting parties or large gatherings is not allowed. Please be considerate of the neighbors and keep noise levels to a minimum, especially during nighttime hours.brbrbrbrPets allowed: Please inform us in advance if you plan to bring pets.brbrbrbrPet Policy:brbrbrbrWe are delighted to welcome your pets to our property. To ensure a comfortable experience for both you and your furry companions, please review our policy and fees:brbrbrbrPlease ensure that your pet is well-behaved and cleaned up both indoors and outdoors. A pet fee of $50 per pet and a $200 refundable deposit is required.brbrbrbrThese policies are in place to ensure a comfortable and enjoyable experience for all guests and to maintain the integrity of the property. brbrbrbrWe offer early check-in or late check-out for an additional fee of $25 per hourbrbrEarly check-in: 2pmbrbrLate check-out: 1 pmbrbrbrbrIf you have any questions or need further clarification about these policies, please contact us. We want to ensure that your stay is pleasant and in accordance with these guidelines.

Remodeled Home with Heated Pool

Siesta Key, Florida, United States

3

Bed

2

Bath

8

Sleeps

$424.42