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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!!”

Cozy Florida Pool Home located near Siesta Key
SUPERHOSTEntire house · 5 guests · 4 beds · 2 baths
Cozy Florida Pool Home located near Siesta Key

Cozy Florida pool home located close to the beach, and walking distance to shops, restaurants, a grocery store, bars, and other stores. It is great for a family (bring your small dog too!), or a couple. The neighborhood is quiet and peaceful with soft church bells ringing in the background at appropriate times. This is a great home for walks, chillin, enjoying Florida, and getting away from it all.

What guests are saying:

“This was our first experience with Airbnb and we were impressed with the ease of finding and reserving a house with features we were looking for. We spent a month at Dan‘s roomy house and enjoyed it a lot. Dan was very prompt in responding to inquiries. The kitchen was well equipped; we even cooked Thanksgiving turkey in the oven. The pool and large covered lanai are definitely a plus. Entry key pad is very practical in that we didn’t have to keep track of a key. The carport kept our rental car out of the sun. Location of the house is in an older neighborhood of Sarasota and very close to a nearby shopping center with a Publix supermarket, various shops (Bed Bath & Beyond, Steinmart, etc.) and restaurants...all within walking distance. The proximity to Route 41 (Tamiami Trail) is very convenient to quickly get to beaches, local sights such as the Ringling Museum (north) and Historic Spanish Point (south). Both are worth a visit.”

"Safe & Clean" Palm Oasis - Relax in comfort!
SUPERHOSTEntire house · 10 guests · 6 beds · 3 baths
"Safe & Clean" Palm Oasis - Relax in comfort!

The Palm Oasis is a 4-bed home with 2000 sqft, only 1 block away to Siesta Key Beach. This home is on one level and has all the amenities including a brand new salt-water pool which is the center of the backyard and a outdoor BBQ grill to make fabulous burgers. Kick back and relax and enjoy this lovely oasis at its finest. All bedrooms offer a flat screen TV. This home offers 1 king, 2 double beds, 1 queen and 2 twin’s beds with 3 full bathrooms accommodation 10 people maximum.

What guests are saying:

“We had a wonderful vacation at the the Palm Oasis! The house, pool, neighborhood and location are all excellent and we would absolutely look forward to staying there again! The hosts were super responsive and helpful. They went above and beyond to ensure our comfort. We rented baby equipment and they even helped coordinate with the rental company prior to our arrival so that everything would be set up when we got there. We’ll be back next year! :)”

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:$230 / night
Fabiola's Studio
SUPERHOSTEntire apartment
Fabiola's Studio
Price:$46 / night
Siesta Key Village Suite 1: a block to the beach!
SUPERHOSTEntire apartment
Siesta Key Village Suite 1: a block to the beach!
Price:$142 / night
Siesta Premier Location  - The 'Calm of Siesta'
SUPERHOSTEntire apartment
Siesta Premier Location - The 'Calm of Siesta'
Price:$149 / night
☀️🏖️NEW Studio w/ OPEN Beach and PRIVATE HEATED Pool
Entire apartment
☀️🏖️NEW Studio w/ OPEN Beach and PRIVATE HEATED Pool
Price:$307 / night
Sea horse · POOL   1 Bed   Sea horse  Walk to beach SPECIALS
SUPERHOSTEntire apartment
Sea horse · POOL 1 Bed Sea horse Walk to beach SPECIALS
Price:$113 / 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:$100 / night
Sparkling Clean! Close to beach & downtown
SUPERHOSTEntire apartment
Sparkling Clean! Close to beach & downtown
Price:$86 / night
"Safe & Clean"  Island Suite  - Siesta Key Beach -
SUPERHOSTEntire apartment
"Safe & Clean" Island Suite - Siesta Key Beach -
Price:$257 / night
Art Nouveau Room Downtown w/ Private Bath
SUPERHOSTPrivate room
Art Nouveau Room Downtown w/ Private Bath
Price:$42 / night
Perfect Getaway Studio,  15 min from Siesta Key
SUPERHOSTEntire apartment
Perfect Getaway Studio, 15 min from Siesta Key
Price:$71 / night
Private 2 Bedroom Suite with Kitchenette
SUPERHOSTEntire apartment
Private 2 Bedroom Suite with Kitchenette
Price:$90 / night
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Pet-friendly houses

Coolest House in Siesta Key Village
Entire house
Coolest House in Siesta Key Village
Price:$349 / night
Cozy Florida Pool Home located near Siesta Key
SUPERHOSTEntire house
Cozy Florida Pool Home located near Siesta Key
Price:$70 / night
Siesta Beach House
Entire house
Siesta Beach House
Price:$175 / night
Siesta Key, large family home.
SUPERHOSTEntire house
Siesta Key, large family home.
Price:$443 / night
Spacious 3/2 home with large pool and yard.
SUPERHOSTEntire house
Spacious 3/2 home with large pool and yard.
Price:$140 / night
Slice of Paradise - Pool house close to Siesta Key
Entire house
Slice of Paradise - Pool house close to Siesta Key
Price:$140 / night
Home on Indian Beach Sapphire Shores Neighborhood.
SUPERHOSTEntire house
Home on Indian Beach Sapphire Shores Neighborhood.
Price:$81 / night
Private Siesta Beach House Oasis with Heated Pool.
SUPERHOSTEntire house
Private Siesta Beach House Oasis with Heated Pool.
Price:$179 / night
Surf View
Entire house
Surf View
Price:$898 / night
The Key Lime Cottage 2 miles from Siesta Key Beach
SUPERHOSTEntire house
The Key Lime Cottage 2 miles from Siesta Key Beach
Price:$62 / night
Boho Beach House:  Walk to Siesta Key
SUPERHOSTEntire house
Boho Beach House: Walk to Siesta Key
Price:$190 / night
Adorable cottage blocks from the bay
SUPERHOSTEntire house
Adorable cottage blocks from the bay
Price:$80 / night
Show all

Houses with pools

Coolest House in Siesta Key Village
Entire house
Coolest House in Siesta Key Village
Price:$349 / night
Cozy Florida Pool Home located near Siesta Key
SUPERHOSTEntire house
Cozy Florida Pool Home located near Siesta Key
Price:$70 / night
"Safe & Clean" Palm Oasis - Relax in comfort!
SUPERHOSTEntire house
"Safe & Clean" Palm Oasis - Relax in comfort!
Price:$425 / night
One-of-a-kind*Beach, Village, Dock & Private Pool!
SUPERHOSTEntire house
One-of-a-kind*Beach, Village, Dock & Private Pool!
Price:$408 / night
4 Bedroom/ 4 Bath Beach House-Directly on Beach!
Entire house
4 Bedroom/ 4 Bath Beach House-Directly on Beach!
Price:$703 / night
Siesta Key, large family home.
SUPERHOSTEntire house
Siesta Key, large family home.
Price:$443 / night
Close to downtown Sarasota home with pool
SUPERHOSTPrivate room
Close to downtown Sarasota home with pool
Price:$49 / night
Siesta Beach House
Entire house
Siesta Beach House
Price:$175 / night
Housing.
SUPERHOSTPrivate room
Housing.
Price:$30 / night
Oceanfront home w/sunset views of Sarasota Bay
SUPERHOSTEntire house
Oceanfront home w/sunset views of Sarasota Bay
Price:$200 / night
Slice of Paradise - Pool house close to Siesta Key
Entire house
Slice of Paradise - Pool house close to Siesta Key
Price:$140 / night
Spacious 3/2 home with large pool and yard.
SUPERHOSTEntire house
Spacious 3/2 home with large pool and yard.
Price:$140 / 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