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Vacation rental beach houses in Siesta Key

Vacation rental beach houses in Siesta Key

Book beachfront vacation rental houses, apartments, and more on Airbnb

Top-rated houses in Siesta Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

Coolest House in Siesta Key Village
Entire house · 5 guests · 2 beds · 2.5 baths
Coolest House in Siesta Key Village

This house is a perfectly decorated and maintained mid century modern masterpiece. The Sarasota School of Architecture style permiates all living spaces, indoors and out. Artwork added to the property in past several years keeps the mid century sex appeal alive and fresh.(Rothko, Calder,Kline,etc.). 8-10 min walk to beach. 1-2 minutes using our 6 3 1 bikes. Cruise back from a day out and enjoy Agnelli built pool and spa. Privacy, Style, Beach and Village, is that what you are looking for?

What guests are saying:

“Gary’s home really is the coolest house on the Key! We have been vacationing in Siesta Key for over 20 years and Gary’s home is the very best place we have ever stayed. We have never experienced working with such a kind, thoughtful, informative, and responsive host. Gary rocks!!! Be sure to make Gary’s home your place to stay when visiting Siesta. You won’t be disappointed and you aren’t going to want to leave! Fantastic home and host!!”

4 Bedroom/ 4 Bath Beach House-Directly on Beach!
Entire house · 13 guests · 5 beds · 3 baths
4 Bedroom/ 4 Bath Beach House-Directly on Beach!

DIRECTLY ON #1 BEACH IN THE USA SIESTA BEACH !!! Walk out of your front door to the sugary white sands of Siesta Key. Enjoy these views from your multiple balconies on 2 separate floors. The large dining room and kitchen are perfect for entertaining. The outdoor entertaining areas and balconies offer the best views in all of Siesta Key. King+sleeper Chair-3 People, King in master-2 people, Bed Three, Queen-2 people, Bed-Four King and queen sleeper-4 people, Living room, Queen sleeper- 2 people

What guests are saying:

“I loved this place and would definitely stay again. It's a three story unit. The garage is downstairs. The living, kitchen, and one room is on the second floor and three rooms are on the third floor. Each room has it's own bathroom. The master has an uncovered patio facing the beach. The living room on the second floor has the second patio, which is partially covered. It's a wonderful view, a wonderful location, and it is beautifully furnished. There is a hose on the side of the unit to rinse your feet off before coming in, and all the beach towels, beach chairs that you will need. At sundown, they do a little service to lower the flag and at sunrise, they do a service to raise the flag. It was a nice touch. We will be back!”

Sunset Beach Studio Newly Renovated In The Village
SUPERHOSTEntire house · 2 guests · 1 bed · 1 bath
Sunset Beach Studio Newly Renovated In The Village

A delightful studio apartment on second floor. Features comfortable queen bed, private bath, full kitchen and outdoor dining table with view of Siesta Key Beach.

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular house amenities in Siesta Key

  • Pool
  • Pets allowed
  • Air conditioning
  • Kitchen
  • Wifi

Apartments in Siesta Key

Beach & Pool Open! Direct Beachfront. Sunset View!
SUPERHOSTEntire apartment
Beach & Pool Open! Direct Beachfront. Sunset View!
Price:GYD48,439 / night
Fabiola's Studio
SUPERHOSTEntire apartment
Fabiola's Studio
Price:GYD9,454 / night
Siesta Key Village Suite 2: a block to the beach!
SUPERHOSTEntire apartment
Siesta Key Village Suite 2: a block to the beach!
Price:GYD27,865 / night
Sand Dollar Studio · Sand Dollar Studio · KING Studio POOL Walk to beach  Brand new SPECIALS
SUPERHOSTEntire apartment
Sand Dollar Studio · Sand Dollar Studio · KING Studio POOL Walk to beach Brand new SPECIALS
Price:GYD19,897 / night
Perfect Loc in Siesta Key!  2 Bedroom 1 1/2 Bath
Entire apartment
Perfect Loc in Siesta Key! 2 Bedroom 1 1/2 Bath
Price:GYD21,008 / night
Siesta Premier Location  - The 'Calm of Siesta'
SUPERHOSTEntire apartment
Siesta Premier Location - The 'Calm of Siesta'
Price:GYD41,386 / night
Private guest apartment 1 block from Sarasota Bay
SUPERHOSTEntire apartment
Private guest apartment 1 block from Sarasota Bay
Price:GYD9,664 / night
Sparkling Clean! Close to beach & downtown
SUPERHOSTEntire apartment
Sparkling Clean! Close to beach & downtown
Price:GYD18,097 / night
Private 2 Bedroom Suite with Kitchenette
SUPERHOSTEntire apartment
Private 2 Bedroom Suite with Kitchenette
Price:GYD18,908 / night
☀️🏖️NEW Studio w/ OPEN Beach and PRIVATE HEATED Pool
Entire apartment
☀️🏖️NEW Studio w/ OPEN Beach and PRIVATE HEATED Pool
Price:GYD82,533 / night
Large modern space in a historic Spanish villa.
SUPERHOSTEntire apartment
Large modern space in a historic Spanish villa.
Price:GYD21,069 / night
Summer Deals!  Updated 1 BD/2 BA, Beach & Pool
SUPERHOSTEntire apartment
Summer Deals! Updated 1 BD/2 BA, Beach & Pool
Price:GYD27,550 / night
Show all

Pet-friendly houses

Coolest House in Siesta Key Village
Entire house
Coolest House in Siesta Key Village
Price:GYD73,319 / night
Siesta Key, large family home.
SUPERHOSTEntire house
Siesta Key, large family home.
Price:GYD88,535 / night
Cozy Florida Pool Home located near Siesta Key
SUPERHOSTEntire house
Cozy Florida Pool Home located near Siesta Key
Price:GYD14,706 / night
Siesta Beach House
Entire house
Siesta Beach House
Price:GYD36,765 / night
Spacious 3/2 home with large pool and yard.
SUPERHOSTEntire house
Spacious 3/2 home with large pool and yard.
Price:GYD29,412 / night
Home on Indian Beach Sapphire Shores Neighborhood.
SUPERHOSTEntire house
Home on Indian Beach Sapphire Shores Neighborhood.
Price:GYD17,107 / night
Slice of Paradise - Pool house close to Siesta Key
Entire house
Slice of Paradise - Pool house close to Siesta Key
Price:GYD30,013 / night
3BR Waterfront Siesta Key Home-Dock-Walk toBeach
SUPERHOSTEntire house
3BR Waterfront Siesta Key Home-Dock-Walk toBeach
Price:GYD25,210 / night
Private Siesta Beach House Oasis with Heated Pool.
SUPERHOSTEntire house
Private Siesta Beach House Oasis with Heated Pool.
Price:GYD37,605 / night
Boho Beach House:  Walk to Siesta Key
SUPERHOSTEntire house
Boho Beach House: Walk to Siesta Key
Price:GYD39,916 / night
Freshly Remodeled Coastal Style Home
SUPERHOSTEntire house
Freshly Remodeled Coastal Style Home
Price:GYD20,447 / night
The Key Lime Cottage 2 miles from Siesta Key Beach
SUPERHOSTEntire house
The Key Lime Cottage 2 miles from Siesta Key Beach
Price:GYD13,668 / night
Show all

Houses with pools

Coolest House in Siesta Key Village
Entire house
Coolest House in Siesta Key Village
Price:GYD73,319 / night
"Safe & Clean" Palm Oasis - Relax in comfort!
SUPERHOSTEntire house
"Safe & Clean" Palm Oasis - Relax in comfort!
Price:GYD89,285 / night
Cozy Florida Pool Home located near Siesta Key
SUPERHOSTEntire house
Cozy Florida Pool Home located near Siesta Key
Price:GYD14,706 / night
4 Bedroom/ 4 Bath Beach House-Directly on Beach!
Entire house
4 Bedroom/ 4 Bath Beach House-Directly on Beach!
Price:GYD137,365 / night
Siesta Key, large family home.
SUPERHOSTEntire house
Siesta Key, large family home.
Price:GYD88,535 / night
One-of-a-kind*Beach, Village, Dock & Private Pool!
SUPERHOSTEntire house
One-of-a-kind*Beach, Village, Dock & Private Pool!
Price:GYD87,094 / night
Close to downtown Sarasota home with pool
SUPERHOSTPrivate room
Close to downtown Sarasota home with pool
Price:GYD10,294 / night
Siesta Beach House
Entire house
Siesta Beach House
Price:GYD36,765 / night
Housing.
SUPERHOSTPrivate room
Housing.
Price:GYD6,303 / night
Spacious 3/2 home with large pool and yard.
SUPERHOSTEntire house
Spacious 3/2 home with large pool and yard.
Price:GYD29,412 / night
YOUR PRIVATE RETREAT NEAR SIESTA KEY BEACH!
SUPERHOSTEntire house
YOUR PRIVATE RETREAT NEAR SIESTA KEY BEACH!
Price:GYD38,445 / night
The Cottage At Central Park
SUPERHOSTEntire house
The Cottage At Central Park
Price:GYD41,807 / night
Show all

Learn more about Siesta Key

What types of vacation rentals are available in Siesta Key?

Here in Siesta Key, there are plenty of options for places to stay. Here are a few examples:
  • Houses (281 rentals)
  • Apartments (84 rentals)
  • Resorts (55 rentals)

Are there houses with pools?

Who doesn’t want a pool at their house? Here in Siesta Key, you’ll find 232 houses that have pools.

What are the top attractions in Siesta Key?

Locals agree that these attractions are worth a visit:
  • Siesta Beach (115 rentals)
  • Siesta Key Drum Circle (94 rentals)
  • Crescent Beach (402 rentals)
  • Sarasota Beach (341 rentals)
  • Siesta Key Beach Parking Lot (126 rentals)

What are some kid-friendly activities in Siesta Key?

Locals agree—these are all great places to take the kids:
  • Siesta Beach
  • Sarasota Beach
  • Siesta Key Drum Circle
  • Siesta Key Village
  • Crescent Beach

What are the top places to eat in Siesta Key?

Whether you’re looking for a tasty treat or a hearty meal, here’s where the locals say to go:
  • The Cottage
  • Daiquiri Deck South Siesta
  • Summer House Steak & Seafood
  • Restaurant Bonjour French Cafe
  • 3.14 Pi Craft Beer & Spirits