Vacation Rentals By Owner In Siesta Key, FL

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolbrbrLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachbrbrVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village - just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, pubs and clubs, shopping, and more, placing this property in one of the most sought after locations on Siesta Key. This Siesta Key condo is well equipped with amenities rarely found in a Siesta Key vacation rental – everything you need to make your stay memorable.brbrThe one bedroom unit is a ground floor condo, approximately 675 square feet with a fully equipped kitchen featuring a glass top range and oven, refrigerator, and microwave. The living room has a large flat panel LCD HD TV. The bedroom has a king-size bed with ensuite bathroom. The bedroom also has a flat panel LCD HDTV. A queen-size sleeper sofa accommodates an additional two guests. The dining room table seats four. The dining room table seats four. Whether you're looking for a romantic getaway, family vacation, or getting away by yourself, this is the perfect hideaway for your vacation! brbrNote: Rates based on occupancy of 2 - additional occupants $105/week up to max occupancy.

One Bedroom - Ground Floor Condo - Heated Pool - Siesta Key Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$489.93

Beautiful 2 Story, 4BR, 3BA Private Home in a quiet neighborhood, Private Pool, Rooftop Deck with Dining Area and Tiki Bar, plus all the home amenities Included. A newly remodeled kitchen/dining area inside, and refreshed linens throughout the house. Just a 3 minute walk to the #1 Beach in the U.S., and a 10 minute walk to Siesta Key Village for Island vibe shops, restaurants, bars, and grocery.

Siesta Key Beach HideAway

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$646.93

Immerse yourself in Bayfront Bliss: Luxe 4-Bed, 3-Bath Retreat just minutes away from the famous #1 beach in America...Siesta Key. This is our newest listing, for our other smaller units and reviews of our other listings, please see Property IDs 2787297, 3223916, and 2946417. Nestled on the picturesque bay, this newly renovated condo offers an idyllic retreat for those seeking relaxation and rejuvenation. With its unbeatable location directly overlooking the tranquil waters, this vacation rental promises breathtaking views and unforgettable experiences for guests of all ages. Whether you're planning a getaway with friends or a memorable family vacation, this waterfront haven has everything you need to create cherished memories that will last a lifetime. As you step inside, you’ll be greeted by a bright and airy living space adorned with contemporary furnishings and stylish decor. The open-concept layout seamlessly connects the living, dining, and kitchen areas, providing ample space for socializing and entertaining. Large windows frame panoramic views of the bay, inviting you to unwind and soak in the natural beauty that surrounds you.brbrThe newly renovated kitchen is a chef’s dream, boasting modern appliances, sleek countertops, and plenty of cabinet space for all your culinary essentials. Whether you’re preparing a gourmet feast or simply brewing a cup of coffee to enjoy overlooking the views, you’ll find everything you need right at your fingertips.brbrWith three bedrooms and two bathrooms, this condo comfortably accommodates up to eight guests, making it ideal for families or groups of friends traveling together. Each bedroom is thoughtfully appointed with plush bedding, cozy linens, and ample storage space, ensuring a restful night’s sleep after a day of adventure.brbrThe master suite is a true oasis of comfort, featuring a luxurious king-sized bed and an en-suite bathroom complete. Wake up to the gentle sound of waves lapping against the shore and sit down to savor your morning coffee as you watch the sunrise over the bay.brbrOutside, utilize the gazebo or pool area to unwind and soak up the sunshine while savoring panoramic views of the bay. Whether you’re enjoying alfresco meals with loved ones or simply lounging with a good book, this outdoor oasis provides the perfect backdrop for relaxation and leisure.brbrOne of the highlights of this vacation rental is its unbeatable location just a five-minute walk from America’s #1 beach. Spend your days basking in the sun on the pristine shores of the Gulf Coast, swimming in the crystal-clear waters, or embarking on exciting water sports adventures such as kayaking, paddleboarding, or jet skiing.brbrBack at the condo, guests will find everything they could ever need or want for a comfortable and enjoyable stay. From beach chairs and umbrellas to beach wagons and beach toys, all the essentials for a fun-filled day by the shore are provided. Additionally, complimentary Wi-Fi, cable TV, and a selection of board games ensure that entertainment options abound for guests of all ages.brbrWhether you’re seeking relaxation, adventure, or a bit of both, this bayfront retreat offers the perfect blend of luxury, convenience, and natural beauty. Book your stay today and discover why this vacation rental is the ultimate destination for your next getaway.

STUNNING Bay View SK Retreat: Newly renovated 4-Bed, 3-Bath Vacation Rental

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$188.94

This is the perfect location on Siesta Key where by day you can walk to, and enjoy, the sun and beach, as well as children’s playground, volleyball, tennis and pickle ball courts. Walk or drive one mile to shopping and dining in nearby Siesta Village. Then, retreat and relax with great evening views from your private lanai overlooking tropical greens, or walk to the beach to see an amazing sunset! After dark, the culture, dining and nightlife of Sarasota are just getting started. Don’t miss it!brbrThe condo is newly renovated and decorated, every detail, right down to the Tommy Bahama queen bed, Ethan Allen king bed, TV’s and fully stocked kitchen. Enjoy the heated pool, four outdoor grilling stations, clubhouse and lush manicured tropical landscaping. Your second floor, two bedroom, two bath condo sleeps six, and is equipped with everything you may need throughout your stay, including beach and pool gear. Laundry facility on site. Simply pack your bags and head to the beach. brbrYour assigned, covered parking space is next to your condo, with easy guest parking nearby. brbrMinimum 14 day stay required. Sorry, no pets/smoking.brThe unit is not ADA accessible.brbrThe first sign that White Sands Village is the right place for you are the grounds, seven acres beautifully landscaped with palm trees, live oaks, flowering shrubs and tropical flowers.brOur pool is heated year-round to a warm 86º, so you can enjoy a swim even during the cooler months. Catch a bit of sun on a lounge chair, or sit in the shade and enjoy a bit of vacation reading.brPublic tennis/pickleball courts are just across the street.brFour lighted gas grills, on the White Sands property, are available for your use.brOne covered parking space is provided for each unit, with additional parking available.brLaundry facilities are available at four locations.brLinens are supplied and kitchens are fully equipped in each of our one- and two-bedroom rental units.brSit by the peaceful lagoon connected to the Intracoastal Waterway.brIn addition to the stunning Siesta Key Public Beach, there are two additional Gulf of Mexico beaches on Siesta Key, as well as great little shops and restaurants. You’ve got easy access to boat rentals, jet ski rentals, parasailing…recreation awaits you!brCrescent Beach, just south of the public beach, is a quieter and more private beach, with only one public access road. Its southern tip is the Point of Rocks, a great snorkeling and diving area with coral reefs that often harbor abundant marine life.brTurtle Beach, south of Crescent Beach, is a great family play area, with a playground, horseshoe pit, boat launch, volleyball court and picnic tables. It’s also a good place for finding shells and perhaps some shark teeth. Here you can launch your boat, fish in Blind Pass Lagoon, or eat in a nearby restaurant.brSiesta Key Village is full of shops and restaurants. You can buy just about everything you need to enjoy your beach vacation, including beachwear, sun products, and toys. There are also little boutique shops where you can indulge your love of unique clothing, jewelry, flowers and scented lotions. Several local restaurants offer patio dining, which you can enjoy from breakfast spots to dinner and evening entertainment.

White Sands is steps away from the cool quartz sand of #1 Siesta Key beach.

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$262.18

Siesta Key Beachside rental on one of the widest and most beautiful stretches of beach in the world. See why Siesta Key’s beach has been rated #1 in the USA! There is a one month minimum for this property. You can be one of the first to stay here after a newly renovated kitchen, paint, floors, tongue and groove ceiling throughout and all new light fixtures and fans. All new furniture throughout the unit. This one bedroom one bathroom villa is only a couple hundred yards to the white sands of siesta beach. No having to cross a busy street, the private beach is yours to use as you please. Use the provided beach chairs for a relaxing day in the sun. This condo has a beachside pool that is unique in Siesta Key and sets this property apart from all the others on the key. One car parking in the carport right next to your kitchen. No having to haul groceries up stairs or on elevators. Very convenient! No pets, no smoking. This is truly a unique property on Siesta Kay. We also own a larger unit right next door! Property ID 934793. Rent both for larger gatherings!brbrPAYMENT SCHEDULEbrbrRefundable security deposit of $500.00 due within 14 days from the date you receive the contract plus $300 for each rental month.brbrBalance of total rent is due 90 days prior to arrival.brbrRates are discounted 5% for the third or more consecutive monthsbrbrStay must be continued occupancy in the same villa.brbrCANCELLATIONbrbrIf cancellation is 90 days or more prior to the rental start date, all monies will be refunded less $50.00 clerical fee.brbrIf cancellation is less than 90 days of rental start date, no refund of monies collected shall be made.brbrNo refunds for early departures.brbrSecurity deposit ($500.00) will be refunded in full for all cancellations. Any changes to the initial contract will be a charge of $50 per changebrbrOccupancy Rates quoted are for:brbrfour (4) people for a two (2) bedroom villabrbrMaximum Occupancybrbr2 bedroom villa - 6 peoplebrbrMust be 21 years of age to rent a villabrbrRecycling Guidelines and Rules & Regulations will be available in each villa. Cleaning fee included in rent.brbrNO PETSbrbrNO SMOKING IN VILLAbrbrTop 10 Beaches in the World 2017 Traveller's Choice Awards! Siesta Key #1 and only beach in the United States recognized!brbr1. Baia do Sancho, Fernando de Noronha, Brazilbrbr2. Grace Bay, Providenciales, Turks and Caicosbrbr3. Eagle Beach, Palm - Eagle Beach, Aruba, Caribbeanbrbr4. Playa Paraiso, Cayo Largo, Cubabrbr5. Siesta Beach, Siesta Key, Florida, United Statesbrbr6. La Concha Beach, San Sebastian - Donostia, Spainbrbr7. Playa Norte, Isla Mujeres, Mexicobrbr8. Radhanagar Beach, Havelock Island, Indiabrbr9. Elafonissi Beach, Elafonissi, Greecebrbr10. Galapagos Beach at Tortuga Bay, Puerto Ayora, Galápagos Islands

The “Petite Suite” on the #1 Beach in America

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$148.65

Sandy Cove is a newly remodeled coastal condo offering stylish comfort, warm natural light, and an easy, welcoming layout that feels relaxing the moment you walk in. The updated interior features fresh finishes, comfortable seating, thoughtful touches, and everything you need for a simple, enjoyable stay. Step outside to a sparkling community pool, beautifully maintained grounds, and convenient beach access that lets you enjoy the shoreline without the crowds. The condo is just a short walk from Siesta Key Village, where you can explore local shops, casual and upscale dining, live music, coffee spots, and the lively island atmosphere. Spend your days at the beach, unwind by the pool, or stroll through the village before returning to a bright, modern retreat designed for a carefree Florida getaway. Whether you’re visiting for rest, adventure, or a little of both, Sandy Cove offers a comfortable home base close to everything Siesta Key is known for.

Luxury Beachfront Apartment

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$270.07

Gulf and Bay Club Unit C209 by Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit C209, a spacious two-bedroom condo in the heart of Siesta Key, located within the beloved Gulf and Bay Club community. This updated coastal retreat offers a bright interior, comfortable furnishings, and convenient access to top resort-style amenities. With a 5-minute walk to Siesta Beach, one of the most beautiful beaches in the United States, this 28-night extended-stay condo is ideal for guests seeking relaxation, comfort, and an unbeatable location near Siesta Key Village and Sarasota’s shopping, dining, and cultural attractions.brbrHighlightsbr• 5-minute walk to Siesta Beachbr• 2 Bedrooms / 1–4 Bathroomsbr• 1 King, 1 Queen, 1 Fullbr• Located in Gulf and Bay Clubbr• Resort-style shared amenitiesbr• Shared pools, hot tub, and spabr• Shared fitness centerbr• Shared tennis and pickleball courtsbr• Washer and dryer in unitbr• One parking spacebrbrGuests of Gulf and Bay Club Unit C209 enjoy access to an impressive selection of resort-style shared amenities that elevate the extended-stay experience. Lounge by one of the sparkling community pools, unwind in the shared hot tub and spa, or keep active in the fully equipped fitness center. Spend sunny afternoons playing tennis, pickleball, shuffleboard, or cornhole, and enjoy access to the expansive clubhouse and recreation facilities throughout the complex. All amenities are located within the Gulf and Bay Club community and available for guest use.brbrThis condo features a welcoming open layout designed for comfort during long stays. The living room includes plush seating and a large TV for relaxing evenings at home. The fully equipped kitchen offers everything needed for easy meal preparation, including a refrigerator, stove, oven, microwave, toaster, dishwasher, and regular drip coffeemaker. Enjoy sit-down meals at the dining area or casual breakfasts before heading to the beach.brbrThe primary bedroom provides a serene retreat with a king bed, ample storage, and access to nearby bathroom spaces. The second bedroom is perfect for families or visiting guests, furnished with a queen bed and full bed for flexible sleeping arrangements. Bathrooms within the unit are conveniently located and designed for comfort, with walk-in showers or tub/shower combinations depending on the configuration.brbrRoom Detailsbr• Primary Bedroom: King bedbr• Second Bedroom: Queen bed and Full bedbrbrThe condo includes a washer and dryer, Wi-Fi access, and all standard household comforts. Outdoor grills, community recreation areas, and beachfront access points are located throughout the Gulf and Bay Club grounds for guest enjoyment.brbrExperience the ease of Siesta Key living at Gulf and Bay Club Unit C209, where resort-style amenities, a comfortable condo layout, and a prime location near world-famous Siesta Beach create the perfect extended-stay getaway. Secure your dates today with Tropical Sands Accommodations.

Gulf and Bay Club Unit C209

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$158.16

Your Siesta Key adventure begins at this delightful 1-bedroom studio. Guests will find a cozy twin bed and a welcoming living room with a comfortable sofa bed, perfect for relaxing after a day of exploring. The space includes a clean bathroom equipped with a hair dryer, and climate control keeps the studio comfortable year-round. Whether you’re unwinding or planning your next outing, this excellent spot offers a peaceful retreat. We’ll be available to answer any questions while you stay at our place.

Apartment

Siesta Key Studio close to beaches, city, and airport.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$411.39

One of a kind at Crystal Sands just steps from one of our two heated pools and only 100 yards from the white sand of Crescent Beach! This well appointed 3 bedroom 2 bath second floor villa sleeps 6 privately boasting beautiful hardwood floors throughout all complimented by the furnishings. brbrVilla 12A offers fantastic privacy and comfortable design, perfect for a group or multiple families.brbrSiesta Key is famous for beautiful turquoise water full of sea life and white powdery crystal sand beaches. Enjoy all our unique features with the convenience of being steps from our own private beach or relax in one of our two heated swimming pools.brbrOur Accommodations are just 2 miles from the popular Siesta Key Village with shops, restaurants, bars, coffee shops and more or a short walk to nearby restaurants, convenience stores, and water sports rentals!brbrIf you are looking for a family vacation or a romantic getaway Crystal Sands is the perfect place for you. Come stay with us at the most exclusive resort on Siesta Key that offers the best beachfront and sunset views on the island!

Crystal Sands Villa 12A

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$246.46

Our beautiful and spacious townhouse is located across the street from Siesta Key Beach. How close is the beach The condo/townhouses complex is on Beach Rd. You only need to go across Beach Rd and walk across the open space public parking, and you will be at the beach. Siesta Key Beach is voted #1 beach in the world, and is known for its white, fine, powdery quartz sand and amazing sunsets. The famous Siesta Key drum circle occur every Sunday 1 to 2 hours before sunset.brAll brand new flooring in the unit were installed Fall 2017.. Kitchen were updated with all new appliances in 2018. Freshly painted in 2019. Our spacious second floor unit is approximately 1400 sq ft. It has a large living room with high ceilings that makes it feel homey. The living room has a floor to ceiling sliding glass door that open to a large balcony with outdoor seating areas that overlooks the emerald green lake, home to some local turtles. brThe elevated formal dining room comfortably seats 6 and has a brand new wood looking porcelain tile floor.brThe master bedroom also has high ceilings and floor to ceiling sliding glass doors to the balcony that overlooks the lake. The master bedroom has a king size bed, new carpets, and a huge walk in closets. The master bath has recently been remodeled with stone tile, walk in shower, granite vanity sink, granite powder room vanity.brThe second bedroom has 2 twin beds that can be combined into a king bed. The second bath is located next to the second bedroom has been remodeled and updated with stone tile & granite vanity sink.brThe fully equipped eat in kitchen has brand new wood looking porcelain floor, and fully stocked with almost everything that you may need. The unit also offers a laundry closet with a stackable washer/dryer.brThe townhome includes a private one car garage (with garage door opener) that is located right below the unit. We provide some beach chairs and beach toys in the garage for your use.brOur House At The Beach offers a large heated pool, two tennis courts, large open gazebo with tables/chairs and a grill. brThis is a non-smoking unit. Smoking permitted on the two outside balconies only.brThe condo has all the towels, linens, beach towels, beach toys, cooler, 10x10 shade, stroller to brings everything to the beach.br

2B/2B 1400sf Siesta Key Townhouse With Parking Garage Across From Public Beach

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$261.01

pClose to sailing, scuba diving, and more, this family-friendly vacation home brings it all within reach. Turtle Beach is an easy 12-minute walk away, so you can leave your car at the property, which offers onsite parking, or jump in your vehicle to make short work of the 5-minute drive to Siesta Key Beach. /ppRelax by the communal pool or sip a drink in the garden of this 557-sq-ft vacation home, which also features a deck or patio and a BBQ grill. When you come inside, connect to the free WiFi or get cozy in front of the Smart TV (video library available). There's also a stereo for your enjoyment. /ppAs you settle into this 1-bedroom, 1-bathroom rental, you'll find a living room, air conditioning, and a desk. Bathroom amenities include a hair dryer and towels. Prepare a home-cooked meal in the kitchen, complete with an oven, a stovetop, and a refrigerator, as well as a coffee maker, a microwave, and cookware. And because there's a washer and dryer, you can go a bit lighter on your packing. /p

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

Bed

Bath

3

Sleeps

$322.03

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. The Tortuga Bungalow features a bright and airy one bedroom space; with a kitchen, bathroom, and a private lanai overlooking Heron Lagoon. With a king-size bed you`ll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. The sofa turns into a queen size bed, allowing for a max occupancy of three.brbrWe are happy to provide free high-speed WiFi internet & HDTV equipped with live sports & extensive channel options via complementary DirecTV Stream, also included are electric appliances so you will not miss a beat. You have your own private lanai, great for lounging or grilling. Take a few steps further and you can enjoy the dock on Heron Lagoon. The resort`s private dock allows for lounging, fishing, or even launching one of our complementary kayaks!brbrIn addition to Heron Lagoon access, this resort has a shared, heated pool and outdoor space that is perfect to bask in the Florida sun! The pool is surrounded by an array of palm trees, Florida`s famous mangroves and tropical plants, providing a beautiful backsplash of greenery and partial shade. On the pool deck, you’ll find numerous sun-loungers to get your tan in, hang-out with friends and family, or just relax :)brbrAdjacent to the pool deck, you can walk out on the shared patio with multiple BBQ-Grills and covered outdoor dining tables. This outdoor space is perfect for a pool fun & grill-outs!brbrResort guests will have access to the heated pool, patio with sun loungers, the dock on Heron Lagoon, kayaks, the courtyard for outdoor eating and grilling, ONE-free-parking (one vehicle max), and a `beach-load-out` that includes beach towels, chairs, cooler, a beach blanket, cart and an umbrella. The laundry facilities are free and shared with other guests. The Tortuga`s lanai and the entire interior of your bungalow is exclusive to you!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches in Siesta Key. Unplug and explore your surroundings, such as Turtle Beach 1-mile south from this location or Crescent Beach, just 2.5 miles north.brbrSporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. From cafes to fine dining in the area to the beautiful Siesta Key beaches, you will certainly find what you need. Did we mention that we provide all guests a complementary ‘beach-loud-out’ that includes beach towels, chairs, blanket, cart, cooler and an umbrella.brbrYou will receive ONE free parking spot on-site, thus if you’re looking to soak up the sun and tour the island in your own vehicle, you always have an easy place to park when you come back. If you don’t want to drive, take advantage of the free Siesta Key Breeze Trolley which stops right outside our parking lot every 20 minutes from 8AM-10PM daily. Siesta Key Dreams is also happy to offer free baggage-drop off to make your travels easier. We also provide on-site golf-cart rental! brbrNote: One parking space per unit, no additional parking.brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement and guest verification, this allows us to provide a safe space and contactless check-in.brbrDo you have a large party Siesta Key Dreams offers 3-bungalow rentals or you can even rent the entire resort!brbrPayment: 50% at time of reservation, 50% 2-days prior to arrivalbrCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM- 7AM brPool Hours: 7AM - 9PMbrNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key DreamsbrPets: No PetsbrParking: One reserved parking space (1 vehicle max)brAdditional Details: See Vacation Rental Agreement for all details

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$255.33

pA short distance from sailing, scuba diving, and more, this family-friendly vacation home lets you experience it all. Turtle Beach is an easy 12-minute walk away, so you can leave your car at the property, which offers onsite parking, or jump in your vehicle to make short work of the 5-minute drive to Siesta Key Beach. /ppAfter you return to this 577-sq-ft vacation home, you can unwind by the communal pool or sip a drink in the garden; you may also like the deck or patio and outdoor furniture. When you come inside, connect to the free WiFi or get cozy in front of the cable/satellite TV (video library available). There's also a stereo for your enjoyment. /ppAs you settle into this 1-bedroom, 1-bathroom rental, you'll find a living room, a BBQ grill, air conditioning, and a desk. Bathroom amenities include a hair dryer, towels, and toilet paper. Prepare a home-cooked meal in the kitchen, complete with an oven, a stovetop, and a refrigerator, as well as a coffee maker, a microwave, and cookware. And you won't have to pack extra clothes, because you'll have a washer and dryer, too. /p

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$206.56

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrCharming Ground Floor Condo in Bay Oaks | Walk to Crescent Beach brbr brbrJust 0.7 miles from Crescent Beach Public Access, this updated 2-bedroom, 1-bath condo in the desirable Bay Oaks community offers the perfect mix of comfort and coastal charm. With 789 sq. ft. of modern furnishings, a screened patio, and access to resort-style amenities, it’s an ideal island escape. brbr brbrLOCATION HIGHLIGHTS: brbr- Located in popular Bay Oaks, featured on HGTV multiple times- Private fishing pier – perfect for sunrises and dolphin watching brbr- Heated community pool and tennis court brbr- Billiard room & clubhouse, BBQ grills & picnic tables brbr- Free covered parking space brbr- Communal laundry facilities (no in-unit washer/dryer) brbr- Just 0.7 miles to Crescent Beach, 7-minute bike ride to Siesta Beach brbr- 0.7 miles to Crescent Beach Public Access brbr- 7-minute bike ride or FREE shuttle to Siesta Key Beach (#1 in the U.S.) brbr- Close to: Restaurants, shops, and entertainment in Siesta Key Village brbr brbrPROPERTY FEATURES: brbr- 2 Bedroom/ 1 Bathroom Condo (789 sq ft) brbr- Dedicated wifi with a smart TV for streaming brbr- Central A/C brbr- Screened patio and outdoor furnishing brbr- Linens and towels provided brbr brbrLIVING ROOM: brbr- Smart TV for streaming brbr- Dedicated wifi brbr- Blu-ray DVD player brbr- Access to screened patio with outdoor dining set brbr- Open living/dining area makes entertaining easy brbr brbrKITCHEN AND DINING: brbr- Open concept layout brbr- Full kitchen with granite countertops, built-in microwave, stainless stove/oven, fridge and dishwasher brbr- Fully stocked with cookware, pots, pans, utensils (no consumables provided) brbr- Dining table for 4 + breakfast bar for 2 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Bedroom: Queen-sized bed with new white wood furniture, two closets, ceiling fans, smart TV for streaming apps (23) brbr- Guest Bedroom: Solid wood bunk bed (twin top, full bottom), bonus extra twin mattress (stored under bed), wardrobe armoire (no closet) brbr- Bathroom: Updated with Corian countertop, large, step-in tiled shower brbr brbrEXTRA PERKS: brbr- Fishing poles provided brbr- Complimentary beach items provided: a couple of beach chairs, beach umbrella. and beach towels brbr brbrNEARBY FAVORITES: brbr- Clayton’s Grill, Miguel’s, Captain Curt’s, Anna’s Deli, Orange Octopus, Crescent Beach Grocery, and more within walking distance brbr- Boat & water sport rentals nearby brbr- Post office close by for sending postcards home brbr brbrIMPORTANT INFO: brbr- Smoke-free, pet-free property brbr- No in-unit washer/dryer (community laundry available) brbr- Rental registration form required brbr- HOA restrictions apply: brbr - No boats, trailers, motorcycles, jet skis, golf carts, or oversized/commercial vehicles unless approved brbr- No access to the private beach entrance across the street brbr brbrBOOK YOUR STAY TODAY AND START MAKING MEMORIES BY THE SHORE!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.brbrIMPORTANT: brbrCarport repair and paving project scheduled to start end of April/early May, 2026. Parking will be disrupted. Please each out for more info.

Poolside Bliss & Powder Sand: Your Gateway to Siesta Key Living at Bay Oaks

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$451.09

Kaia's Sun and SeabrNewly remodeled with pool and jacuzzi, just 1-minute walk to Siesta Key beach! Poolside lounging and grilling, sunsets, sandbars, and on reef snorkeling and paddling. Just 4-min walk to shopping dining bars and live music. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Front Porch – southwesterly porch on the palms (shared)br∙ Beaches – 1-min walk to award winning beaches, white sand, calm waterbr∙ Relaxing – private balcony and patio with dining and loungingbr∙ Pool – beautiful heated pool with tropical plants just 1-minute walkbr∙ Reef Snorkeling – 70-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 –1-minute walk to best sunsets and whatever comes nextbr∙ 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 BeachbrAccess to two private Siesta Key beaches. With no public parking nearby, this cove is one of Siesta's more 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 4-minutes two 12 bars and restaurants. Walk 7-minutes to Siesta's top eco-adventures boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe at the beach, nap by the pool 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 Coasts 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 unit is two flights up with no one above it. There is a king bedroom, a queen bedroom and a sectional sofa. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels and the resort supplies chairs and umbrellas. 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. 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. 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 | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$493.02

Palm View UnitbrTop floor bayside unit with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bay-front lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Resort Amenities – heated pools, jacuzzi, gym, pickle, tennis, and boat moorsbr∙ The Balcony – royal palm views from balcony connecting bedrooms and living areabr∙ The Grounds – fishing causeway, private bay and beach access, lined by royal palmsbr∙ Private Beach – 4-min walk to private beach and Siesta Key's widest whitest sandsbr∙ Restaurants – 2-min walk to free trolley to all Siesta's shopping dining and entertainmentbr∙ Sunsets –walk 4-min to best sunsets in America or just enjoy from your balconybr∙ Activities – scooter, golf cart, bike and kayak rentals nearby br∙ 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 – perfect fit for all with resort amenities and trolley to all top attractionsbr brbrThe BeachbrOur beach is a private Siesta Key beach with the widest whitest sands, free chaise lounges, and umbrella rentals. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.brbrThe LocationbrWith so many amenities, and all of it free of charge, a 3-night stay here will feel like a two-week getaway. If you get the most from a vacation when you don't have search or worry about anything, this unit is not a plus for you it's a must! Although you could easily take a free trolley 1-mile any direction to dozens of shops and restaurants, you can also satisfy every vacation desire without ever putting on your shoes or leaving this resort. You can swim in pools or in the Gulf, fish the inter-coastal, exercise in the gym, sleep in the sun, explore Siesta Key's best beach, make Sandcastles, and even sightsee all in a safe environment and right on your property. The beach here has the whitest sand on the island, but some of the best moments are watching boats and dolphins pass from the private balcony or nearby bay-front pool.brbrBedroom DetailsbrThis is a 3rd-floor (top) unit with an elevator. This two-bedroom unit has a king bedroom, a queen bedroom, and a sofa in the living room. You can sleep up to 6. If you need more space, I can get an additional unit nearby. brbrBeach Gear ProvidedbrWe provide beach towels, and the resort provides free chaise loungers and umbrella rentals. If you have any issues just reach out and we will do whatever we can. 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.brbrImportant Resort Limitsbr1) Expect a special experience where each visitor's peaceful enjoyment is respected. The minimum age for visitors not accompanied by a parent or guardian is 25 years. Stay up as late as you want, but the “quiet neighbor times” begin 10 PM. After 10 PM relocate the party to nearby Siesta Village or the Crescent Beach area. 2) Just one parking space per unit. However, cars are not necessary and an additional emergency parking space is available 1 mile away. If any of these limits are not a fit for you, please let me know, I have other properties available.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, private laundry, 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. 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. 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 | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$676.28

Siesta Sun by Siesta Key Luxury Rental Properties is a stunning 3 bedroom, 3. and a half bath Siesta Key luxury rental located just a 1-minute walk to Siesta Key Beach. This elevated duplex offers beach views, a private rooftop deck with sweeping Gulf scenery, and a bright coastal interior perfect for extended stays, family vacations, and groups seeking refined yet relaxed island living. With access to a shared tropical pool, a lively game room, and pet friendly accommodations. Siesta Sun delivers effortless coastal comfort near Crescent Beach, island restaurants, and the Siesta Key Breeze Trolley. brbrHighlights br• 1-minute walk to Siesta Key Beach br• Beach views and rooftop deck br• 3 Bedrooms / 3.5 Bathrooms br• 3 Kings and Daybed with Twin Trundle br• Screened dining area and BBQ grill br• Shared tropical pool br• Game room with foosball and bar seating br• Dog friendly (with approval) br• Washer and dryer in unit br• 3 parking spaces brbrWake up to island sunshine and head up to your private rooftop deck, where lounge chairs and panoramic Gulf views set the tone for a perfect Siesta Key morning. The shared backyard features a sparkling pool surrounded by tropical landscaping and plenty of comfortable seating, ideal for afternoons between beach visits. You’ll also enjoy a screened dining balcony with a BBQ grill, perfect for easy outdoor meals. The downstairs game room adds a fun, casual hangout option with foosball, bar seating, and a refrigerator for drinks and snacks. brbrInside, a spacious open concept layout pairs coastal style with comfort. The living room offers plush sofas, a large TV, and built in shelving that adds charm and character. The kitchen is fully equipped with stainless steel appliances, ample counter space, bar seating, and cookware. The dining area seats eight and opens seamlessly to the screened balcony, creating an inviting indoor-outdoor flow that complements the island lifestyle. brbrThe primary bedroom features a king bed, TV, coastal decor, and access to the balcony. Its ensuite bathroom includes a double vanity, a beautifully tiled walk-in shower, and a large walk-in closet. The second bedroom also includes a king bed, balcony access, and a private ensuite bathroom with a shower and tub combination. The third bedroom offers a king bed, TV, and access to the hallway bathroom with a shower/tub combination. On the way to the rooftop deck, a cozy den includes a daybed with a twin trundle, providing additional sleeping space. brbrRoom Details br-Primary Bedroom (2nd floor): King bed, balcony, ensuite bathroom with walk-in shower br-Second Bedroom (2nd floor): King bed, balcony, ensuite bathroom with shower/tub combo br-Third Bedroom (2nd floor): King bed br-Den (3rd floor): Daybed with Twin Trundle and rooftop access brbrThis home includes a rooftop deck, screened dining area, BBQ grill, shared pool, lounge seating, balconies, washer and dryer, and three parking spaces. Located along Beach Road and just steps from the Gulf, Siesta Sun offers unbeatable walkability to shops, island eateries, Crescent Beach, and the Siesta Key Breeze Trolley. Larger groups can reserve the neighboring duplex, Island Sun, for a combined six-bedroom coastal retreat. brbrSiesta Sun by Siesta Key Luxury Rental Properties blends elevated coastal design with unbeatable proximity to the beach. From Gulf view rooftop sunsets to relaxing poolside days, this home offers everything you need for a memorable Siesta Key escape. Book your stay at Siesta Sun today and experience the best of Siesta Key! brbr- brThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Steps from Beach. Roof Top Deck-Gulf Views. Shared Heated Pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$678.44

Summary:brbrContemporary 3 Bedroom 3 Bath Luxury townhome. Beach views from the 3rd bedroom on top floor with full bath and bonus room and murphy bed. Master suite with tub and walkin shower, Gourmet kichen, leather furniture, balcony with partial views of the Gulf from the 3rd floor balcony. Laundry in unit, 2 car garage (only parking for 2 cars in garage) Pool shared by other half of unit (spa is non-functional and is maintained at pool temperature.) Tub/shower combination in guest bath is a shower only. Unit provides highspeed internet service, Short distance to Siesta Village and just across the street from Siesta Beach access. Unit has elevator. Unit Sleeps 8, 2 King, 1 Full murphy bed and full blow up. NO SMOKING, NO PETS NO MOTORCYCLES, CAMPERS, TRAILERS, RV'S ALLOWED IN DRIVEWAY. 1 week min..

439 Beach Rd

Siesta Key, Florida, United States

3

Bed

3

Bath

8

Sleeps

$329.49

Jamaica Royale Unit 096 – Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale Unit 096, a freshly remodeled two-bedroom, two-bath villa tucked within the beloved Jamaica Royale community on world-famous Siesta Key. Just steps from the resort’s private stretch of powder-soft sand, this bright and inviting coastal escape offers easy access to community amenities and the island’s laid-back charm. Whether you are planning a weeklong getaway or an extended winter stay, this comfortable villa captures the relaxed Florida lifestyle Siesta Key is known for.brbrHighlightsbr• Private beach accessbr• Shared pools and shuffleboard courtsbr• 2 Bedrooms / 2 Bathroomsbr• 1 King bed, 2 Queen bedsbr• Completely remodeled interiorbr• Washer and dryer in unitbr• One assigned parking space directly outsidebr• Two community BBQ areasbr• Beach chairs provided at the sea wallbr• Shared clubhouse and recreation roombrbrSpend your mornings strolling the private beach, coffee in hand, and your afternoons relaxing by one of the community’s sparkling heated pools. Challenge friends to a friendly game of shuffleboard, or grill your fresh catch at one of the two outdoor BBQ areas. The Jamaica Royale community is loved for its quiet atmosphere, beautifully kept grounds, and easy beach access, making it a favorite for long-term guests and seasonal visitors alike.brbrStep inside to a completely refreshed interior filled with coastal hues and comfortable furnishings. The open concept living and dining area features plenty of natural light, plush seating, and a flat-screen TV for movie nights. The fully equipped kitchen offers modern appliances including a refrigerator, stove, oven, dishwasher, microwave, toaster, and coffeemaker, with ample counter space to make mealtime simple.brbrThe primary bedroom features a king bed, ceiling fan, and ensuite bathroom with a walk-in shower and single vanity. The second bedroom includes two queen beds and its own bathroom with a walk-in shower and vanity, providing an ideal layout for families or friends traveling together. Each room is tastefully furnished to create a calm, restful retreat after days in the Florida sun.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroom with walk-in showerbr• Bedroom 2: Two queen beds, shared hallway bathroom with walk-in showerbrbrGuests will enjoy a washer and dryer in the villa, high-speed Wi-Fi, and convenient parking directly outside the unit. Community amenities include access to three shared heated pools, shuffleboard courts, BBQ grills, and a recreation room, all steps from your door.brbrRelax, recharge, and make lasting memories on Siesta Key at Jamaica Royale Unit 096. With its newly updated interior, peaceful community setting, and prime location near Siesta Beach and the Village, it is the perfect island escape for snowbirds and families seeking sun and simplicity. Book your stay today with Tropical Sands Accommodations and experience the comfort of classic Siesta Key living.

Jamaica Royale Unit 096-Freshley remodeled

Siesta Key, Florida, United States

Bed