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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.

Beachfront Getaway in Siesta Key
Entire house · 4 guests · 2 beds · 1 bath
Beachfront Getaway in Siesta Key

Beachfront complex, this gorgeous home boasts all the luxury you’d expect from a beach house! Beachfront BBQ grills, cabana with lounge chairs,heated swimming pool, Wi-Fi & parking. For your convenience, there are restaurants, grocery store, pharmacy, 24 hours 7-Eleven, bike and Kayak rentals just across the street. A little piece of paradise!

What guests are saying:

“My family and I loved this spot! It was small but it had everything we needed to enjoy the private access beach (chairs, coolers, etc.) that was right down the little path. And it was nice and clean. We also took advantage of the grill and pool! The location was perfect! Take note of the early check-out time though.”

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!”

The Cottage At Central Park
SUPERHOSTEntire house · 5 guests · 3 beds · 1 bath
The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

What guests are saying:

“This house was EXCELLENT! It is located in a quiet, nice neighborhood, but is only a block over from the main road to access everything you need! The house was super clean and beautifully decorated! The beds were comfortable and the couch bed was good too! Montana was an excellent host. She was super quick to respond to any questions we had. She and her husband came right over to help with the tv when we couldn’t figure it out. They had a book with local suggestions for food and things to do. The house had a great pool! They also had beach towels, chairs, toys and other stuff to use for the beach or pool! We will definitely be staying again next time we are in town! We couldn’t have asked for a better place and host! We were sad to leave!”

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

Charming Apt. in old Florida home
SUPERHOSTEntire apartment
Charming Apt. in old Florida home
Price:$46 / night
Fabiola's Studio
SUPERHOSTEntire apartment
Fabiola's Studio
Price:$47 / night
Sarasota Downtown close to Lido Beach
SUPERHOSTEntire apartment
Sarasota Downtown close to Lido Beach
Price:$68 / night
Lido Beach House - cute retro studio.
SUPERHOSTEntire apartment
Lido Beach House - cute retro studio.
Price:$126 / night
★ NEW ★ Gorgeous hideout | A+ LOCATION & Pool ★
SUPERHOSTEntire apartment
★ NEW ★ Gorgeous hideout | A+ LOCATION & Pool ★
Price:$120 / night
Lido Key/St. Armand's Studio
SUPERHOSTEntire apartment
Lido Key/St. Armand's Studio
Price:$104 / night
Sweet Apartment in Sarasota FL
SUPERHOSTEntire apartment
Sweet Apartment in Sarasota FL
Price:$46 / night
UNIT 1 AT SIESTA KEY BEACH VILLA
SUPERHOSTEntire apartment
UNIT 1 AT SIESTA KEY BEACH VILLA
Price:$160 / night
Large modern space in a historic Spanish villa.
SUPERHOSTEntire apartment
Large modern space in a historic Spanish villa.
Price:$102 / night
Steps To The Beach
Entire apartment
Steps To The Beach
Price:$260 / night
Lido Beach House - two bedroom mid-century heaven
SUPERHOSTEntire apartment
Lido Beach House - two bedroom mid-century heaven
Price:$255 / night
Modern Spacious 2/2 Ready for You!
SUPERHOSTEntire apartment
Modern Spacious 2/2 Ready for You!
Price:$96 / night
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Pet-friendly houses

Tropical Escape
SUPERHOSTEntire house
Tropical Escape
Price:$118 / night
Private Siesta Beach House Oasis with Heated Pool.
SUPERHOSTEntire house
Private Siesta Beach House Oasis with Heated Pool.
Price:$176 / night
Modern Funky Pool Home - Sleeps 10!!
SUPERHOSTEntire house
Modern Funky Pool Home - Sleeps 10!!
Price:$150 / night
Private cozy home surrounded by oaks and pines.
Private room
Private cozy home surrounded by oaks and pines.
Price:$43 / night
Secluded luxury with heated Saltwater Pool & Spa
SUPERHOSTEntire house
Secluded luxury with heated Saltwater Pool & Spa
Price:$220 / night
PARADISE RETREAT SIESTA KEY/WE ARE YOUR BEACH NOW
SUPERHOSTEntire house
PARADISE RETREAT SIESTA KEY/WE ARE YOUR BEACH NOW
Price:$300 / night
A Few Min to Siesta, Heated Pool/Spa, Grill, WiFi
Entire house
A Few Min to Siesta, Heated Pool/Spa, Grill, WiFi
Price:$164 / night
Siesta Beach House
Entire house
Siesta Beach House
Price:$175 / night
Home on Indian Beach Sapphire Shores Neighborhood.
SUPERHOSTEntire house
Home on Indian Beach Sapphire Shores Neighborhood.
Price:$80 / night
The Daiquiri Deck
Private room
The Daiquiri Deck
Price:$311 / night
The McClellan House - Close to Everything
SUPERHOSTEntire house
The McClellan House - Close to Everything
Price:$120 / night
Siesta Oasis - Month Rentals, htd pool, huge yard!
SUPERHOSTEntire house
Siesta Oasis - Month Rentals, htd pool, huge yard!
Price:$199 / night
Show all

Houses with pools

Beachfront Getaway in Siesta Key
Entire house
Beachfront Getaway in Siesta Key
Price:$188 / night
4 Bedroom/ 4 Bath Beach House-Directly on Beach!
Entire house
4 Bedroom/ 4 Bath Beach House-Directly on Beach!
Price:$549 / night
The Cottage At Central Park
SUPERHOSTEntire house
The Cottage At Central Park
Price:$199 / night
The Oasis-Heated Private Pool Hot Tub-5mi to beach
SUPERHOSTEntire house
The Oasis-Heated Private Pool Hot Tub-5mi to beach
Price:$150 / night
Private Siesta Beach House Oasis with Heated Pool.
SUPERHOSTEntire house
Private Siesta Beach House Oasis with Heated Pool.
Price:$176 / night
Modern Funky Pool Home - Sleeps 10!!
SUPERHOSTEntire house
Modern Funky Pool Home - Sleeps 10!!
Price:$150 / night
"Safe & Clean"  Our Beach House
SUPERHOSTEntire house
"Safe & Clean" Our Beach House
Price:$279 / night
★Monthly Discount★Pool + SmartTVs★Great location!★
SUPERHOSTEntire house
★Monthly Discount★Pool + SmartTVs★Great location!★
Price:$124 / night
Secluded luxury with heated Saltwater Pool & Spa
SUPERHOSTEntire house
Secluded luxury with heated Saltwater Pool & Spa
Price:$220 / night
Sarasota house with Pool
SUPERHOSTEntire house
Sarasota house with Pool
Price:$122 / night
Siesta Beach House
Entire house
Siesta Beach House
Price:$175 / night
The Daiquiri Deck
Private room
The Daiquiri Deck
Price:$311 / 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