Siesta Key Holiday Rentals, Florida: Private House Rentals

A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

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Go beyond your typical stay in Siesta Key

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Our top choices for Siesta Key hotels

A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.

An outdoor patio with a fire feature, seating, and a bar area.

A hotel lobby with a reception desk, a refrigerator with beverages, and a microwave.

A hotel reception area with a wooden reception desk, a large abstract mural, and a seating area with a view of greenery outside.

1. Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

Jose

฿3,279

฿3,706 total

includes taxes & fees

4 Oct - 5 Oct

A pool area with a waterfall feature, lounge chairs, and palm trees.

A covered patio with a brick floor, wicker furniture, and tropical plants.

A beach with white sand, clear blue water, and a few beach umbrellas.

A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.

2. Tropical Beach Resorts

South Village

kurt

฿4,542

฿6,006 total

includes taxes & fees

4 Oct - 5 Oct

A beach with several beach chairs and umbrellas, a small table, and a few people relaxing.

An outdoor seating area with blue cushioned sofas and tables, a thatched roof, and a sign for Big Tiko Lounge.

A swimming pool with blue lounge chairs and palm trees.

A bedroom with a bed, two bedside tables, a ceiling fan, and a window with blinds.

3. Siesta Key Beach Resort and Suites

Siesta Key Village

Vanessa

฿4,916

฿7,416 total

includes taxes & fees

5 Oct - 6 Oct

A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

A modern living room with a flat-screen TV, a round coffee table, and a sofa.

A bedroom with a bed, two bedside tables, a ceiling fan, and windows with curtains.

A narrow concrete pathway flanked by white walls, leading to a lush green area with palm trees and a small grassy patch.

4. SeaSpray Resort

Siesta Key

Michelle Suzanne

฿8,433

฿9,529 total

includes taxes & fees

13 Oct - 14 Oct

A beach with people sunbathing and swimming.

A modern kitchen with white cabinetry, a white dining table, and a chandelier.

A modern kitchen with white cabinets, a dining area with a white table and chairs, a blue sofa with white cushions, and a ceiling fan.

A tropical resort with a thatched-roof hut, a wooden bench, and a white fence.

5. Siesta Key Beachside Villas

Siesta Key Village

Alberta

฿4,488

฿6,933 total

includes taxes & fees

4 Oct - 5 Oct

A covered outdoor area with a pool, lounge chairs, and a wooden deck.

A bar area with a wooden ceiling, bar stools, and a neon sign.

A swimming pool with lounge chairs and palm trees, surrounded by string lights.

A nighttime view of a tropical resort with a water feature, palm trees, and ambient lighting.

6. Siesta Key Palms Resort

Sarasota

Jonathan

฿1,755

฿3,692 total

includes taxes & fees

8 Oct - 9 Oct

An outdoor patio with a grill, white chairs, and a red umbrella.

A modern apartment with a living room, a dining area, a kitchen, and a TV mounted on the wall.

A modern kitchen with a stainless steel refrigerator, a microwave, and a sink with a faucet.

A spacious room with wicker furniture, a television, and a window with a view of parked cars.

7. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

฿4,276

฿4,832 total

includes taxes & fees

15 Oct - 16 Oct

A coastal cityscape with a wide beach, beachfront hotels, and a clear view of the ocean.

A room with a wooden cabinet, a TV on the wall, and a wooden floor.

A bedroom with a bed, bedside tables, a wardrobe, and a window with blinds.

A room with a blue patterned wall, a wooden floor, a blue sofa, a wooden bench, and a bed with a white headboard.

8. Azul at Siesta Key Inn

South Village

Adrian

฿3,190

฿3,605 total

includes taxes & fees

6 Oct - 7 Oct

An aerial view of a beach with white sand, clear turquoise water, and several umbrellas.

A residential area with a paved walkway, a house with a visible number '8' on the door, and a garden with various plants and a palm tree.

A residential area with houses, a swimming pool, and a sign indicating 'Twin Palms 1115'.

A nighttime view of a swimming pool surrounded by palm trees and a brick pathway.

9. Twin Palms at Siesta

Siesta Key

Leonardo

฿5,520

฿6,237 total

includes taxes & fees

22 Oct - 23 Oct

A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

A dining table with glassware and decorative branches, set outdoors with a house in the background.

A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

A narrow concrete pathway flanked by lush tropical plants, leading to a wooden gate.

10. Captiva Beach Resort

South Village

Karla

฿5,454

฿6,733 total

includes taxes & fees

6 Oct - 7 Oct

A stone pathway leading through a tropical garden with palm trees and a signboard.

A couple walking on a beach with clear skies and ocean waves.

A modern living room with a large flat-screen TV, a sofa, and a dining area with a table and chairs.

An outdoor patio with wicker furniture and a thatched roof.

11. Tropical Breeze Resort

Siesta Key Village

Lara

฿4,994

฿6,321 total

includes taxes & fees

4 Oct - 5 Oct

A bedroom with a bed, a TV, a wooden dresser, and a bathroom visible through an open door.

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a multi-story building.

12. Cottages at Siesta Key Inn

South Village

Jonathan

฿3,533

฿4,472 total

includes taxes & fees

4 Oct - 5 Oct

A pool area with lounge chairs, palm trees, and a building with balconies.

A dining area with a table set for six, wooden cabinets, a kitchen in the background, and a window with blinds.

A spacious living room with a dining area, a fireplace, and a large window.

A balcony with wicker furniture, a glass table, and a view of a swimming pool and palm trees.

13. Siesta Key Inn

South Village

Mary Ellen

฿5,116

฿6,474 total

includes taxes & fees

4 Oct - 5 Oct

A living room with a sofa, armchair, coffee table, and a potted plant.

A gated pool area with a white fence, a clear sky, and a building with multiple windows in the background.

A bedroom with a bed, a ceiling fan, a TV, a dresser, a mirror, and a window with blinds.

A hotel courtyard with outdoor seating, a covered area, and a building with multiple windows.

14. Siesta Vibe Pool Walk To Crescent Beach

South Village

฿4,012

฿13,098 total

includes taxes & fees

10 Oct - 11 Oct

A covered outdoor area with a wooden table and chairs, a white door, and a yellow wall.

A room with a bed, a sofa, a table, and a ceiling fan.

A kitchen with a coffee maker, a can of POM, and a sink.

A yellow house with a porch, a mailbox, and a number 5306 on the door.

15. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

฿4,960

฿12,326 total

includes taxes & fees

4 Oct - 5 Oct

A clear turquoise sea with people swimming and a boat in the distance.

A palm tree with a clear blue sky in the background.

A pool area with lounge chairs and a brick pathway.

A spacious living room with wicker furniture, a leather sofa, a flat-screen TV, and a fireplace.

16. Siesta Palms By the Beach

South Village

Aaron

฿6,233

฿9,889 total

includes taxes & fees

2 Oct - 3 Oct

A pair of stacked front-loading washing machines in a commercial setting.

A parking area with a red pickup truck, a concrete barrier, and a sign with text.

A compact kitchen with a microwave, oven, and refrigerator. There are two stools and a small table with a kettle.

A patio with a sun lounger, a table with chairs, and an umbrella.

17. Beach View 100ft To Beach and SPA

Siesta Key Village

฿4,537

฿11,848 total

includes taxes & fees

4 Oct - 5 Oct

A compact living space with a kitchen, a dining area, and a sofa with cushions.

A staircase leading to a door with a welcome mat, a television on a stand, and a wooden ceiling.

A mobile home with a porch, a small deck, and a sliding door.

A compact living space with a sofa, a television, a ceiling fan, and a door.

18. Tiny House Siesta

Sarasota

Staci

฿2,095

฿6,901 total

includes taxes & fees

8 Oct - 9 Oct

A swimming pool with a 3 ft 3 in depth marker, surrounded by lounge chairs and a covered seating area with a view of the water.

A sandy beach path with wooden posts and ropes, leading towards the ocean.

A wooden deck with chairs and a table overlooking a body of water.

A narrow stone pathway flanked by lush green plants and a wooden pergola structure.

19. Turtle Beach Resort

Siesta Key

Melanie Anne

฿6,679

฿8,522 total

includes taxes & fees

1 Nov - 2 Nov

An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

A pool area with lounge chairs, a staircase, and a building with balconies.

A waterfront hotel with a marina, palm trees, and high-rise buildings in the background.

A modern building with a flat roof, large windows, and a covered outdoor area with seating.

20. Beach Club at Siesta Key Poolside D

South Village

Jeff

฿6,702

฿18,009 total

includes taxes & fees

8 Oct - 9 Oct

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Holiday Rentals in Siesta Key

Aparthotel

Tropical Beach Resorts

South Village

"Amazing resort,"

Aparthotel

SeaSpray Resort

Siesta Key

"Property and room were beautiful!! Right across the street from the beach ⛱️"

Aparthotel

Hibiscus Suites - Gateway to Siesta Key

Sarasota

"This place was perfect!"

Condo

Captiva Beach Resort

South Village

"Clean room, beach access, easy parking, friendly staff"

Mobile Home

Tiny House Siesta

Sarasota

"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."

Holiday Home

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A modern living room with a beige sofa, a coffee table, and a chandelier. There is a kitchen area in the background with a dining table and chairs.

A modern kitchen with a built-in island, stainless steel appliances, and a dining area with a view of the outdoors.

An aerial view of a beach with white sand, clear turquoise water, and a grassy area with paths.

Siesta Key Island Rentals

Siesta Key

"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"

Cottage

A modern kitchen with white cabinets, a coffee bar, and a dining area with a view of the sea.

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

A cozy living room with a stone fireplace, a flat-screen TV, a sofa, a coffee table, and a dining area with chairs.

The Inn On Siesta Key

Siesta Key

"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."

Apartment

A living room with a stone fireplace, a television on a white cabinet, and a large window with a view of greenery.

A blue building with a garden pathway, palm trees, and a clear blue sky.

A coastal area with a beach, buildings, and greenery.

The Ringling Beach House

Siesta Key

"Nice kitchen and clean place"

Holiday Home

A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

A spacious living area with a large bed, a sofa, a small table, and a kitchen in the background.

A wooden deck overlooking a calm river, surrounded by lush greenery and trees.

A modern kitchen with stainless steel appliances, a central island with bar stools, and a window with blinds.

Siesta Heron Suites & Villas

Siesta Key

"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"

Apartment

A balcony with wicker chairs and a small table, overlooking a white house with a pool and palm trees.

A backyard with a swimming pool, surrounded by a white fence, palm trees, and a patio area with chairs and an umbrella.

A compact living space with a kitchenette, a sofa, a coffee table, and a bed.

A wooden pathway leading to a turquoise building with a sign indicating directions to Sunshine, Starfish, and Seashell.

Siesta Key Dream Inn Rental - Close to Village!

Siesta Key Village

Condo

Beach Club at Siesta Key Poolside D

South Village

"Nice getaway. "

Holiday Home

A spacious living area with a staircase, a white sofa set, wicker chairs, a coffee table, and a chandelier.

A pool area with lounge chairs, a wooden deck, and a wooden fence.

A modern living room with a white sofa, wicker chairs, a fireplace, and a television.

A spacious dining area with a long table set for six, white chairs, a chandelier, and a staircase leading to an upper level.

Canal-front Sleeps 10 Pool Spa Private Dock

Siesta Key

"Location was great, property layout was good, but there is no bathroom on the main floor, which is a bit frustrating when you are in the pool and need the facilities. Kitchen was well equipped, there were plenty of towels in the linen closet and they had a ton of beach toys, chairs, wagons in the garage which is nice. The beach is close, but its a long hike in the sand if you're carrying stuff, so use those carts. Sliders in the main living area need some blinds because that afternoon sun is HOT...

Condo

A playground with slides and climbing structures, surrounded by palm trees and a clear sky.

A living room with two grey sofas, a television displaying a beach scene, two palm trees with string lights, and a ceiling fan.

Pineapple Cove Walk to Beach

South Village

"Great !"

Condo

An aerial view of a beachside hotel with a tennis court, palm trees, and a sandy beach.

A modern living room with a sofa, chairs, a dining area with a table and chairs, a TV, and a ceiling fan.

House of The Sun Siesta Key Crescent Beach

South Village

"The area is beautiful. The condo was very nice. Has everything in it. You can cook if you prefer. The Gulf of Mexico was right behind the condo walk out on to the beach. It also has a pool. I have no complains I would def go back again . "

Condo

Beach Club Cute Cottage in C Bldg

South Village

"Nice hotel and stay. "

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Where to stay in Siesta Key

Find the best Siesta Key areas for the activities you enjoy most.Learn more about Siesta Key

A vibrant building with a purple facade, a sign reading "Siesta," and a staircase leading to the entrance.

A beach club with outdoor seating, a bicycle, and a parking sign.

A street scene with a clock tower, a speed limit sign, and a sign for 'Avenidaissima'.

A colorful storefront with a T-shirts section and a swimwear section.

A beachside area with colorful rental cars, a surf shop, and a thatched-roof building.

Siesta Key Village

This lively beach hub sits adjacent to Siesta Beach, one of America's top-rated shorelines. The compact village streets are lined with open-air restaurants, tiki bars, and colourful beach boutiques. Palm trees sway above outdoor dining patios where sunset cocktails flow freely. Travellers can easily explore the area on foot, enjoying live music that drifts from waterfront venues. The sugar-white sands and crystal-clear Gulf waters are just steps away. Shop for local crafts at the Siesta Key Farmers Market or simply relax in this quintessential beach paradise.

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A sunset over a body of water with a dock and palm trees.

Bay Island

Bay Island offers a secluded paradise within Siesta Key with direct access to award-winning beaches. This exclusive waterfront community features luxury homes with private docks and stunning views of Sarasota Bay and the Gulf of Mexico. Pristine waters surround this affluent enclave where privacy comes standard. The island serves as a perfect base for exploring nearby attractions. Shell Beach and Lido Beach lie just minutes away by car. Travellers can easily visit Marie Selby Botanical Gardens or browse upscale shops at St. Armands Circle in neighbouring Sarasota.

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A large, beige colonial-style building with columns, surrounded by palm trees and dense vegetation.

A sunset over a body of water with a silhouette of vegetation in the foreground.

South Village

If you're spending some time in South Village, Safe Harbor Siesta Key and Crescent Beach are top sights worth seeing.

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Aloha Kai

Aloha Kai offers a peaceful retreat on Siesta Key with direct access to world-renowned white sand beaches. This residential haven features luxury holiday rentals and condominiums set against the stunning backdrop of the Gulf of Mexico. The neighborhood's contemporary coastal architecture blends perfectly with manicured tropical landscapes. Walk along waterfront paths with views of both the Gulf and intracoastal waterways. The crystal-clear waters are ideal for swimming year-round. While quiet within its boundaries, Siesta Key Beach, Crescent Beach, and Siesta Key Village are just minutes away.

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Bailey Hall

Bailey Hall might not have many top sights, but Siesta Key Beach and Lido Beach are two attractions nearby that you can check out.

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Stay near popular Siesta Key attractions

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Siesta Key Beach

9.6/10 (4,113 reviews)

Siesta Beach captivates with its unique quartz sand that stays cool even on hot days. Sink your toes into the powdery white shoreline while gazing at the clear turquoise waters that make this beach a favourite.

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A sandy beach with people sunbathing and umbrellas, clear blue sky, and calm sea.

Turtle Beach

9.0/10 (1,163 reviews)

If a restful holiday is part of your travel plans, Turtle Beach might be the perfect place to visit during your trip to Siesta Key. Wander the seaside or discover the sunsets in this relaxing area.

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A sunset over the ocean with silhouettes of people and tall grasses.

Crescent Beach

9.4/10 (815 reviews)

Crescent Beach offers powdery white quartz sand that stays cool even on scorching days. Explore the nearby Point of Rocks for exceptional snorkelling among vibrant marine life.

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A beach with a pier, palm trees, and calm ocean waters under a clear sky.

Point of Rocks

9.2/10 (444 reviews)

Dramatic limestone formations jut into the Gulf, creating a vibrant marine ecosystem for snorkellers. Explore clear waters teeming with colourful fish and coral during high tide for the best underwater views.

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A coastal town with a beach, marina, and residential area.

Shell Beach

9.2/10 (164 reviews)

Escape the crowds at this secluded north Siesta Key shoreline with pristine white sand and clear Gulf waters. Bring your own supplies and arrive early to secure one of the limited parking spots.

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A lifeguard tower with green and yellow colors, stairs, and a beach in the background.

Irma Beach

8.4/10 (66 reviews)

Escape to Irma Beach's soft white sands and tranquil waters on Siesta Key. This serene coastal retreat offers a more intimate experience away from the crowds of Florida's busier shores.

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Siesta Key Beach Playground

This beachside playground offers separate play areas for different age groups, all just steps from Siesta's famous white sand. Enjoy shaded structures while the kids play, then cool off with a quick dip in the Gulf.

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Siesta Key Farmers Market

This vibrant market showcases 30 local vendors selling fresh produce, artisanal goods, and handcrafted jewellery. Browse unique offerings while enjoying live music in this community gathering spot.

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Learn more about Siesta Key

The powdery white sand of Siesta Beach feels cool underfoot even on the hottest summer days. Rent a paddleboard at sunset to glide through the calm Gulf waters and spot dolphins arcing alongside you.

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