Vacation Condo Rentals By Owner In Siesta Key, FL

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

Bed

Bath

Sleeps

$377.4

Indulge in the laid-back luxury of this beautifully remodeled condo at Crescent Arms, just steps from the pristine shores of Siesta Key Beach, named #1 in the USA! Recently updated with a new kitchen, bathrooms, and chic coastal decor, this vacation rental offers the perfect blend of comfort and style. Step out the door and sink your toes into the powdery white sands and crystal-clear Gulf waters that make Siesta Key famous. Inside, create culinary delights in the fully equipped kitchen, relax in the comfortable living room, and soak in partial beach views from your screened balcony. For those needing to stay connected, a dedicated workspace is located just off the kitchen. Both bedrooms offer ensuite bathrooms and balcony access: the primary suite features a king bed, and the second bedroom has two twin beds. Crescent Arms offers direct access to Siesta Key Beach and a community pool. Beyond the beach and pool, discover the vibrant Siesta Key Villages, both offering live music, shops, and restaurants (South Village - 0.5 mile, North Village - 2.5 miles), or explore the local scene in Gulf Gate (2 miles), known for its diverse dining and unique shops. Book your unforgettable Siesta Key escape today!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! There are beach chairs available on the beach at the property and umbrellas available for rent.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!

Eternal Sunshine | Beachfront Community w/ Pool - Steps to Siesta #1 Beach!

Siesta Key, Florida, United States

Bed

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

Bed

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

Bed

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

Bed

Bath

Sleeps

$345.09

Enjoy this darling 1-Bed, 1-Bath condo, located just half a block from the powdery white sand of the world-famous Siesta Key Beach! With a lovely open floor plan, this little home offers a wonderful décor, a kitchenette, living room with a sleeper sofa and a bedroom with a king size bed. Relax by the pool under the warm island sun, or take the quick stroll into the Siesta Key Village for the many great shops and restaurants the island has to offer. Walk down the Sunset beach to take in the stunning views and spectacular sun sets. If you feel like venturing off the island, Siesta Key is located just 20 minutes from Sarasota International Airport and just minutes from the downtown area of Sarasota and all it has to offer. Sarasota is the Cultural Gem of the Gulf Coast. It offers numerous galleries, theaters, and some of the finest restaurants in the world. You will not be bored with this location. The list of activities is nearly endless as you can spice up your vacation with bike, kayak, or boat rental for your entertainment. This unit is sure to be a lovely Gulf Holiday for you and your family that will have you returning year after year!brbrBedroom 1 – KingbrLiving Room – Queen Sleeper SofabrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 23br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $500

One Bed/ One Bath Condo- Step From Siesta Key Beach with Pool On Property!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$314.91

Welcome to our newly renovated two bedroom, one bath, ground floor condo on Siesta Key. Located on the IntraCoastal side there is a waterway on the property. Private access to the beach right across the street. Best of both worlds! Heated pool, tiki bar/grill, and fishing pier on the property. Halfway between Siesta Key Village and the shops at south bridge, restaurants, bars, and stores are easily accessible. The free trolley can take you from one end of the island to the other.brbr- Free wifi is provided in the condo! br- The kitchen is fully equipped with all the essentials including new dishes, pots and pans, coffee maker, toaster, fridge, cookware, glasses, silverware, etc.br- The master bedroom has a king sized bed and dresser.br- The second bedroom has 2 twin beds.br- The living room includes a pull-out queen sofa bed, coffee table, end-tables and flat screen cable tv.br- Sizeable vanity top for bathroom essentialsbr- There are two chairs by the front door to sit back and relax. There is also a private patio at the back of the condo.br - we provide beach chairs, beach umbrellas, beach towels, beach toys for kids and a beach cart to easily carry things to the beach.br- Convenient free parking right outside the front door. Please note trailers or RVs are not allowed.brbr- You have full access to every space in Sea Club II. The club room, swimming pool, fishing pier, tiki bar/grilling areabr- 5 minutes walking to our private beach access across the street.br- Laundry facilities are on-site and are coin or credit card accessible. br- The free trolley takes you from one end of the island to the other.brbrBring your fishing poles as you have the option to fish off our pier.br brIf you are interested in paddle boarding, parasailing, jet-skiing, scootering, you can find nearby rental facilities.br brSiesta Key provides activities during the day as well as a great nightlife with live music, outdoor beach bars and terrific weather year round. Siesta key also provides fabulous restaurant options that you don’t want to miss.

Renovated Siesta Key Condo, beach/heated pool access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$335.83

Escape to Siesta Key and enjoy our cozy ground floor condo, just steps away from a private beach. This fully equipped one-bedroom, one-bath unit comfortably sleeps four with a queen pull-out sofa. Amenities include smart TVsl, on-site laundry, and free assigned parking and Wi-Fi. Perfectly located between Siesta Key Village and the shops at south bridge, with easy access to restaurants, bars, stores, and the free trolley. Book now for a dream vacation on the world-famous Siesta Key Beach! brbr- The kitchen is fully equipped with all the essentials including new dishes, pots and pans, coffee maker, toaster, fridge, cookware, glasses, silverware, etc.br- The bedroom has a king sized bed , dresser and flat screen tv.br- The living room includes a pull-out queen sofa bed, comfortable chairs and flat screen cable tv.br- Sizeable vanity top for bathroom essentialsbr - we provide beach chairs, beach umbrellas, beach towels, a cooler, frozen ice packs, beach toys for kids and a beach cart to easily carry things to the beach.br- Convenient free parking right outside the front door. Please note trailers or RVs are not allowed.br- The condo is on the gulf side a minute's walking to the world famous white sand beach, Chairs/loungers are available at the private beach.br- Convenient ground floor condo, no need to climb stairs.br- Laundry facilities are on-site. br- Access to temperature controlled pool.br- Quiet and safe dead-end street makes it ideal for safety. No through traffic.br-The free trolley takes you from one end of the island to the other.brbrIf you are interested in paddle boarding, parasailing, jet-skiing, scootering, you can find nearby rental facilities.br brSiesta Key provides activities during the day as well as a great nightlife with live music, outdoor beach bars and terrific weather year round. Siesta key also provides fabulous restaurant options that you don’t want to miss.

Newly renovated beachside condo - direct beach access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$462.76

5 Stars for over 15 years on VRBO! Beautiful, quiet, 2 minute walk to the beach!!brMajor renovation complete in January 2020. Brand new kitchen, appliances, tile flooring and fresh new paint. Beautiful Siesta Key Condo at Peppertree Bay. Gulfside unit just a 2 minute walk to the beach and pool. Crescent Beach was voted #2 most beautiful beach in Florida on Travel Channel. You will never run out of exciting things to do! Fishing, exercise room and Tennis Courts on site. Or just relax on the sugar soft sandy beach or go seashell hunting. Beachwalkers paradise, Walk one mile South to the 'Point of Rocks' or head North for a 5 mile round trip beachwalk to the 'Big Pass' on the northern point. Generally a very quiet beach but gets very busy at Spring Break and the July 4th fireworks show. Also Boat Races draw a big crowd for July 4th. FREE WIRELESS INTERNETbrbrKeywords: Beach Home, Island Home, Paradise, Beach House, Walk to the beach, Peppertree, Siesta Key, Crescent Beach,

Siesta Key Gulfside 3BR, 2.5BA Condo, an Island Paradise. steps to the beach.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$196.95

Come and enjoy the island lifestyle on Siesta Key in this lovely furnished 3rd floor condo. Enjoy your morning coffee or evening cocktail on the balcony with views of the beautiful inter-coastal waterway from your vacation home. Beach access to Siesta Key’s famous Crescent Beach quartz sand beach is within walking distance. The property is located on lush grounds, amazing community pool, boat basin, tennis courts, pickle ball, basketball, fitness room & BBQ area. Includes the convenience of an in unit washer and dryer and carport. Come and enjoy the Florida lifestyle with breathtaking sunsets, nearby restaurants and entertainment, Siesta Key village & convenient free Siesta Key trolley. Just a short drive over the bridge to the mainland for even more cultural adventures and fun.

Relaxing Siesta Key Condo

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$197.12

Beautifully furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paving stones carports parking, our air-conditioned condo offers two large newly installed wood-like flooring bedrooms with 2 full baths (in-suite master bathroom with new vanity & ceramics), a comfortable living room, fully equipped kitchen with newly installed cabinets & granite counters, dining area, HD cable TV, music entertainment center, Magic Jack telephone system with unlimited calling within the US & Canada and lanai (balcony) with a view of the tropical gardens. All necessary linens are provided, and full-sized coin-operated or App-operated washers and dryers are located downstairs. brNear the intersection of Beach and Midnight Pass Roads in Siesta Key, across (7 -10 minutes walk) from world-renowned Siesta beach, the # 1 beach in the USA & 4th best in the world.brThere is a heated swimming pool, his and hers saunas, two common BBQ areas, club house, private boat docking area, and private covered off the road reserved parking. Free WiFi is available at the condo and pool/clubhouse area. brPlease, see the Condo Virtual Tour in the provided video.brSiesta Key has some 150 stores, galleries, boutiques, salons and specialty shops in Siesta Key village and other locations. There is also a great selection of bars and restaurants. Additionally, downtown Sarasota is a short drive across the north and south key bridges with its renowned shopping, fine dining, and cultural attractions. Free tennis & pickleball courts are steps away from the complex on the way to Siesta beach.brbrThere is a charge for the departure cleaning service and a two week minimum stay policy. brbrOther Amenities include 2 TV's (a 40 in living room with HD cable & a 27 in master bedroom), CD & DVD players, Comcast Xfinity cable TV, dishwasher, microwave, telephone, toaster oven, coffee maker, iron, hair dryers, ceiling fans in living / dining room & master bedroom, beach chairs and umbrellas. Children are welcome (a playpen is available in the 2nd bedroom closet that can serve a young baby up to 2 years old). brbrCoin operated laundry facilities are available in the first floor of the building. You can download the clean cash App on your phone to pay for your laundry for more convenience.brbrOne small dog , 25 lbs or less, is allowed. Assistance dog is allowed with a proof. The management office has the right to reject an over-sized dog.brbrOnce payment is made to the site, Guest Registration Form will be sent to the guests. This form must be completed by the guests, scanned and emailed back to the owners to forward to the Condo Association. Alternatively, guests can send to the owners a clear legible photo of the completed form. Also, a Rental Agreement (Lease) will be sent to the the Guests to sign & return to the owners, together with the complex (WSV) Rules & Regulations.brbrPlease note that for the Winter Months (January - March): Reservations will only be accepted from the 1st or the 15th of the month. Priority for this period will be given to full month(s) rent. As for all seasons reservations, min is 14 days in case full month(s) reservations cannot be secured.brbrA detailed Check-In / Check-Out procedures, together with House & pet rules will be provided to the guests a few weeks before the arrival date.brbrVrbo has a Card on File policy by which guest credit card can be charged for damage, if host submit a claim for damage within 14 days of departure.

2 BR Condo-Short Walk to Siesta Beach/ One 25 lbs Dog Allowed / E. Bird Specials

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$290.54

Nestled in a prime location with high-season availability, Condo 210 is the perfect beach retreat, offering 1,220 sq. ft. of space, 2 spacious bedrooms, and 2 luxurious bathrooms. This condo has been upgraded with everything you need for a relaxing and memorable stay.brbrMaster Bedroom Sanctuary: Sleep soundly on the ultra-comfortable king-sized bed. The master suite also features a large, spa-like walk-in shower for a truly relaxing experience.brbrGuest Bedroom Flexibility: The guest room is equipped with a queen bed and en suite bathroom.brbrGourmet Kitchen: The modern, fully-equipped kitchen features top-of-the-line amenities, including a Keurig coffee maker and Ninja blender—perfect for morning coffee or afternoon smoothies.brbrEntertainment Ready: Unwind and enjoy your favorite movies on the 65 smart TV, or take advantage of the condo's beach gear, including towels, linens, beach chairs, and umbrellas—no need to carry anything but your essentials!brbrEndless Beach Fun: Simply pack your swimsuit, sunglasses, sunscreen, and flip-flops, and you’re ready for a day of sunbathing and sandcastle-building on the world-famous Siesta Key Beach. After a day in the sun, relax with a glass of wine on the screened-in lanai while watching breathtakingbrbrThis condo is the ultimate beach vacation dream come true. Book now and make it a reality!

Sunsets and Sand 2 Bed 2 Bath Siesta Key Beach with Full Gulf Views

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$292.24

SIESTA KEY IS CALLING! LOOKING TO ESCAPE THE COLD WEATHER THIS WINTER!!! brbrLOCATIONLOCATION,LOCATION!!! We have an amazing fully equipped condo with monthly rentals in Siesta Key, FL. Perfect for boating and beach lovers. This 2 bedroom, 2 bath first floor condo with a one car garage on Siesta Key will fulfill all your dreams! Spend the day on the famous Siesta Key Beach (just steps away from the #1 beach in the USA) with our beach chairs and cart and come back and enjoy the fish jumping from your personal lanai! This unit is located in a gated community in the heart of Siesta Key! The trolley stop is also in front of the complex which will take you to both villages or downtown Sarasota. Play tennis/pickle ball on the private courts, lounge by the heated pool or fish out your back door.brbrYou will need to provide information to the association for a basic background check prior to accessing this rental, this includes vehicle details. A short phone call may be required with the association to acquaint you with the property.

Waterfront 2-bedroom condo across from the beautiful Siesta Key Beach with AC

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$282.63

This spacious first floor waterfront condo has over 1879 sq. of indoor/outdoor living space. Boasting two gigantic elevated private outdoor patio’s with outdoor furniture, along with water views of the Intercostal, direct access to marina, designated parking and your own private entrance. Siesta Key Beach #5 in the World #1 in the USA 2017!! Plus Harbor Towers is like a Resort community with all the amenities! Check out our new video.br brFeaturing 9 foot ceilings, comfortably sleeps 6 with two bedrooms plus a full size murphy bed in the den with closet. The inviting master suite has a king bed and en suite including full travertine shower and sitting area with view of the marina. Enjoy the unique option of using the den as a home office or a third bedroom. Second Bathroom tub/shower has been completely updated with granite and travertine.br brThe kitchen is completely equipped and updated with granite countertops, stainless steel appliances and dining table seats up to 10. Four TV’s are provided for every room along with cable and DVD player a 60” TV in the family room with state of the art sound system. You are just a few steps adjacent to the washer and dryer access.br brGated with security 24 hours a day, the condo’s two pools can’t be compared, including the “best kids pool on the Key”. Three lighted Har-Tru tennis courts along with an active tennis community and large workout facility. Four Gas grills for your use and a massive indoor/outdoor dining area. Fish off the pier or grill out while relaxing in the gazebo just a stroll over the private bridge.br brJust a short walk to the white sands of the #1 Beach in the US! Beach cart is included for all your beach toys, chairs, towels and a cooler. Siesta Village with all of its night life and fabulous restaurants is a mere 1.5 miles away.br br• Renovated 2025- with updated all new bathroomsbr• Decorated furnishings by the team from Design Elegance - featuring 9 ft ceilingsbr• Two huge elevated private patios with sweeping Intercostal viewsbr• Kitchen cabinets and drawers fully equipped br• New 2021 refrigerator, microwave, dishwasher, ovenbr• Small kitchen appliances and utensils br• Dining table and chairs with 10 chair's and 2 leavesbr• New mattress pads and bedding br• Den has full size murphy bed with box springs, home office with printer and patiobr• 4 flat screen TVs, 60, 48,48 and 32”, (2 are smart TV's)free cable, password protected WI-FIbr• 2023 Newly Renovated bathrooms stocked with new linensbr• Washer and dryer just steps away condo doorbr• Phone for local calls and entrance door usagebr• Two heated poolsbr• Three Har– Tru lighted Tennis courtsbr• Marina dock to the baybr• Outdoor gas grills and picnic tablesbr• Social room, vending machines, gamesbr• Weight/exercise roombr• Gated secured building and parking lot with night guardbr• Designated Parking near condo private entrancebr• Florida is the Golf capital of the world a golfers paradisebr• Siesta Village Restaurants, shops, museums, nightlife, aquarium, activities nearby br• Harbor Towers requires guests to stay a minimum of 14 days

Spectacular Waterfront - Panoramic Views of Intercostal 3 Bed- 2 Bath

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$153.72

This bright and relaxing condo includes 2 bedroom (1 King) (1 Full/Twin bunk bed) Full kitchen including dishwasher, coffee pot, basic utensils. Washing/Dryer, Air Conditioning, Wi-fi, 3 TVs with cable in the living room and each bedroom. brbrFrom your screened lanai it is only steps to the gated heated pool. Steps from your front door is a covered assigned parking spot. The community rec center includes a pool table, and coin-op laundry facilities. Bay Oaks has incredible scenery surrounding the intracoastal waterway, including a beautiful dock and community grilling area.br brThis location is only a free ride (Thanks to Johnny’s Free Rides) or a short bike ride from siesta key village and Siesta Key Beach! Siesta Key beach is the #1 Rated Beach in America with the whitest and most beautiful sands. Renting bicycles on the key is popular and very convenient from this location. You are only a 10 minute bike friendly ride away from great restaurants and shops like Daiquiri Deck, Gilligan’s Island Bar & Grill, and Siesta Key Oyster Bar. brbrThis condo has a lot to offer. Please read our profile for full list of amenities br

Poolside Condo minutes from Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$299.45

The luxurious condo is located on Siesta Key in a tropical setting. It is very kid-friendly, and has a private beach, only within 5 minute's walk, on the world-famous Siesta Key Beach (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico.brbrThe minimum rental period is 1 week (condo association rule), starting any day of the week.brThe condo is located right on Siesta Key, in a tropical setting. It is in a luxurious condominium, very kids friendly, and has private access to the world-famous (Best Beach in the U.S.A.) Siesta Beach with crystal white sand and turquoise waters of the Gulf of Mexico. The sand in Siesta Key Beach is 99% quartz and never gets too hot under the sun. The condo is only 500 yards away from the beach. The complex has a private garage, The condo is in a hidden paradise and offers heated pools (2), lighted tennis courts, pickleball courts, a fishing pier overlooking the gorgeous waterfront views, barbecue grill areas (2), picnic areas, a sauna, a fitness room, artificial lakes, promenades and a clubhouse for private parties.brThe condo is minutes away (walking distance) from the lovely Siesta Key Village with restaurants, bars with live music, coffee shops, retail, and gift shops. It is also very close to the famous Crescent Beach (walking distance) and Turtle Beach.brThe condo is about 20 minutes away from Sarasota Airport and about 1 hour to Tampa International Airport. Orlando is only about 2 hours drive, where you can visit Disney World, Legoland, Universal Studios, Space Center, etc.brbrbr

5 minutes to private Siesta Key Beach + 2 heated pools and pickleball courts

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$377.77

This beautiful two-bedroom, two bath condo is located just steps from the famous white sands of Siesta Key Beach. That means there are no streets to cross to access our private, gated beach. The stunning sunsets never get old and the blue/green ocean waters are so inviting. It’s no surprise that Siesta Key Beach is rated the best beach in the USA. On a 90-degree day, the white quartz sand is still cool on the feet. It is almost like magic. brThis newly remodeled, newly furnished and decorated condo sleeps 7 people. From Travertine stone floors; to marble and granite counter tops; to large beautiful showers; to very comfortable furniture and large screen TVs; it just doesn’t get any better! There is a king bed in the master suite; two queen beds in the spare bedroom, and a single murphy bed in the lanai that kids will fight over. Both bedrooms have private entrances to their bathrooms.brThe living room consists of all leather furniture with a matching recliner, and will comfortably seat 6 adults. The living room has a 75-inch, 4k Smart TV, and the bedrooms each have 55-inch flat screen Smart TVs. Just bring your Roku or Firestick to plug into the smart TVs and it’s as if you are sitting at home. We also have Comcast cable with all the local and national channels. Wi-Fi is free throughout the complex and installed on the TVs for your use. brThe kitchen is fully stocked with a fridge with ice maker, microwave, dishwasher, blender, and a Keurig coffee maker. In addition, it is completely stocked with all the pots and pans for any type of cooking that you would like to do. It is also equipped with all the dinnerware and flatware to accommodate 8 persons. There is a breakfast bar that seats 2 persons and a dining room table for 6. brPeppertree offers two large, heated swimming pools and a workout room equipped with several pieces of exercise and weight lifting equipment. Bathrooms and showers are also available at the pool locations. Peppertree offers tennis and pickle ball courts for your use as well. A community room can be reserved for small gatherings with friends and family. There are gas grills with seating scattered throughout the Peppertree property for your use. brEnjoy a private covered parking space at ground level under the building for your vehicle. In addition, a storage container at this location contains beach chairs, umbrellas, beach toys, etc. for your enjoyment. If you are bringing a bicycle or renting one, we have an area for storage.br If you are flying in to Siesta Key and not renting a car, no worries. There is a free trolley system that runs 7 days a week from morning until 11:00 pm every day, as well as many other free types of transportation.brPlease be sure and browse the pictures and most importantly, enjoy your stay!

Peppertree #206 Beautiful 2-bdrm, 2 bath condo on World Famous Siesta Key Beach

Siesta Key, Florida, United States

3

Bed

Bath

8

Sleeps

$249.77

Harbor Towers Unit 509 by Tropical Sands AccommodationsbrbrHarbor Towers Unit 509 is an updated two-bedroom, two-bath condominium located on the fifth floor of the Harbor Towers Yacht and Racquet Club. Designed with comfort and privacy in mind, this residence features two primary-style bedroom suites, water views, and beautiful sunset vistas, making it an ideal option for couples enjoying an extended stay on Siesta Key.brbrHighlightsbr• 13-night minimum staybr• 2 Bedrooms / 2 Bathroomsbr• Ideal for two couplesbr• King bed and Queen bedbr• Two private ensuite bathroomsbr• Fifth-floor residence with water and sunset viewsbr• Vinyl flooring throughoutbr• Fully equipped kitchenbr• Gated waterfront communitybr• Two heated pools and three Har-Tru tennis courtsbrbrGuests at Unit 509 enjoy Harbor Towers’ resort style amenities along the Intracoastal Waterway, including two heated swimming pools, three Har-Tru tennis courts, and a 40-slip marina. Additional shared features include fitness and sauna facilities, grilling areas, a waterfront gazebo, and scenic seawall seating where guests can enjoy boat activity and local wildlife.brbrThe condo is comfortably furnished and tastefully decorated, offering a relaxed and inviting atmosphere. The living area provides a welcoming space to unwind while enjoying water views and sunset skies. This space flows seamlessly into a fully equipped kitchen, stocked with everything needed to prepare meals or enjoy takeout while watching boats pass along the Intracoastal Waterway.brbrThe first primary suite features a king bed and an ensuite bathroom with a walk-in shower. The second primary suite offers a queen bed and a private bathroom with a tub and shower combination. Towels and bed linens are provided for guest convenience, making it easy to settle in for a longer stay.brbrRoom Detailsbr• Primary Suite One: King bed, ensuite bathroom with walk-in showerbr• Primary Suite Two: Queen bed, ensuite bathroom with tub and showerbrbrWith its two suite layout, sunset views, and access to Harbor Towers’ exceptional waterfront amenities, Harbor Towers Unit 509 by Tropical Sands Accommodations is a comfortable and convenient home base for enjoying island life. Relax by the pool, watch the boats drift by, and settle into the easy rhythm of Siesta Key. Book your extended stay and make this your coastal retreat.

Harbor Towers 509 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$322.58

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Our House at the Beach West, 5th Floor Corner Unit! brbr brbrNew listing in a prime Siesta Key location! This 5th-floor West Tower condo at Our House at the Beach offers stunning west-facing views of the world-famous Siesta Key Beach, with heated pool and tennis courts on-site. Enjoy bike rides, jet skis, sunset cruises, or relaxing on the soft, powdery sand—your perfect beach vacation awaits! brbr brbrLOCATION HIGHLIGHTS: brbr- Across the street from the beach, beach views brbr- Heated communal pool, grills. tennis courts brbr- About 1.25 miles to Siesta Key Village - enjoy a nice evening walk or jump on the nearby trolley stop brbr- Golf carts are welcome brbr brbrPROPERTY FEATURES: brbr- 2 Bedroom/ 2 bathroom 5th floor condo (1698 sq dt) brbr- Wrap-around private balcony with views of the beach brbr- Floor to ceiling sliders brbr- Dedicated WIFI (complex is currently making upgrades to the wifi) brbr- Self check in brbr- Assigned parking spot brbr- Central A/C with ceiling fans brbr- Private washer and dryer brbr brbrLIVING ROOM: brbr- Open, spacious layout with tons of natural light brbr- L shape couch with additional seating brbr- Panel-style sliding blinds for adjustable comfort brbr- WiFi and DirecTV included brbr- Balcony access with full views of Siesta Key Beach brbr brbrKITCHEN AND DINING: brbr- Full kitchen with stainless steel appliances, granite countertops brbr- Equipped with pots, pans, dishes, utensils, small appliances brbr- Dining table seats 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Bedroom: king bed, en-suite bathroom, large closet, full ocean views brbr- Guest Bedroom: queen bed, east-facing island views, closet, no cable TV but has streaming capabilities brbr- Blow-up queen air mattress available for two people brbr- Master ensuite bathroom: vanity with tub/shower combo brbr- Guest bathroom: walk-in shower with vanity brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrNEARBY FAVORITES: brbr- Daquiri Deck, Siesta Key Oyster Bar, Another Broken Egg, Old Salty Dog brbr- Siesta Market, Beach Club, Big Tiki Lounge brbr brbrIMPORTANT INFO: brbr- No pets allowed brbr- No smoking/vaping brbr- Parking restrictions: No boats, trailers, motorcycles, oversized or commercial vehicles allowed brbr brbrPLEASE NOTE: A window and door replacement project is scheduled for the West Tower during August, September, and October 2026. Work will be done between 8am-4pm and there may be noise from construction. brbr brbrWE'D BE DELIGHTED TO HOST YOU AND HELP MAKE YOUR SIESTA KEY STAY TRULY MEMORABLE!brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Ocean Views in Our House at the Beach, Full Gulf Views from Balcony, Heated Pools!

Siesta Key, Florida, United States

Bed