Vacation rentals with a pool in Siesta Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Siesta Key

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Condo in Siesta Key

4.9 out of 5 average rating, 101 reviews

*Open* Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

Guest favourite

Home in Siesta Key

4.92 out of 5 average rating, 115 reviews

Siesta Peace Retreat a private home rental

Comfortable and peaceful 1.4 miles from the beach; 1 mile to the village. I have 4 beach bikes and beach gear. Plenty of chairs, an umbrella, towels and coolers. Beautiful private saltwater pool in quite neighborhood. Very comfortable and peaceful retreat. Firesticks on 3 televisions. I do not allow large gatherings or parties. I do live in a separate home on the property. I travel a lot so guests usually only see me at check in. I give lots of local tips, tricks and foodie advice.

Guest favourite

Condo in Siesta Key

4.96 out of 5 average rating, 295 reviews

On the Beach; Siesta Key SunBum Studio

STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.

Guest favourite

Condo in Siesta Key

4.83 out of 5 average rating, 145 reviews

The Key to a Great Vacation!

Welcome to our one bedroom, one bath (4 piece) main floor condo. Recently renovated. Freshly painted with new furniture, a brand new king size memory foam mattress with contemporary decoration (with queen size pull out couch). Easily accessible with no steps to climb and close, convenient parking right outside the front door. Quiet, peaceful and near both Siesta Key Beach and the condo pool ensure a wonderful vacation. Walk across the street and enjoy one of the best beaches in the world.

Guest favourite

Condo in Siesta Key

4.94 out of 5 average rating, 107 reviews

Seaside Sanctuary

This condo is set in the perfect location between the beach and the bay! Soak up the sun at the heated pool, enjoy the tiki bar, or try your luck fishing on the pier, all while viewing the boats on the intercoastal! Included is private deeded beach access that is just a easy 5 min walk. Hop on the free trolley right outside your door to go to Siesta Key Village with plenty of restaurants, bars and shops only .5 miles away. 65" tv free wifi Netflix Disney+. Boat slip available up to 24'

Guest favourite

Condo in Siesta Key

4.93 out of 5 average rating, 192 reviews

Steps away from beach and village! #1 in Siesta!

The Little Sandy... Your secret hideaway Incredibly located Two bedrooms, one bath Sleeps 6 easily Bring the kids...or not Walk everywhere. 3-minutes to the beach, 8 to Siesta Village Super-fast Wi-fi! Icy A/C Lovely pool Play in the water, play on the sand, play in the village Rinse and repeat Comfy beds, soft towels A great night's sleep And the best hosts on Airbnb Tradewinds included free of charge. So book now and find your Siesta-self Just like you, only funner.

Guest favourite

Guest suite in Sarasota

4.93 out of 5 average rating, 304 reviews

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *Private Studio* Access Non shared Pool. Studio w/private entrance & private patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/local markets/ dining/movies & shopping New King bed. New 50" TV. Off street parking. No Smoking/Vaping! Wet Bar, No kitchen, lite meals only! No hotels in my exclusive area! Live like a local!

Guest favourite

Rental unit in Sarasota

4.87 out of 5 average rating, 114 reviews

Little gem just 6 min from Siesta+heated pool

WE HAVE POWER, WATER AND INTERNET ★ "Second floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" • 6 min drive from Siesta • Shared heated pool just 200 feets • Screened lanai • pet friendly, no pet fee, no deposit • Fully stocked kitchen • 555 sqft home • walking distance Publix, restaurants, bars • 30 min. drive from SRQ Airport • 60 min. drive from Tampa Airport • 8 min. drive from I-75 • 20 min. drive from the downtown and St. Armand Circle

Guest favourite

Serviced apartment in Siesta Key

4.99 out of 5 average rating, 165 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Beautiful Apartment at Siesta Key Beach. Fully equipped. Condo hotel, on the best area of the beach in Siesta. Chairs and lounge chairs included. Beach pool, shade pool (heated), gym, 3 tennis courts on site (2 clay, 1 hard) and 2 pickle ball courts. Master bedroom with King bed. The Mattress is a SAATVA ORGANIC. 2nd room with 2 single beds, and a queen sofa bed, in the living room. Pack n Play & high chair for children. 600 MB Wifi. 70” Smart TV, 2 55” TVs Nesspreso, Keurig.

Superhost

Condo in Siesta Key

4.82 out of 5 average rating, 205 reviews

New: Cozy 1BR Beach Condo on Siesta Key!!!

Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.

Guest favourite

Condo in Sarasota

4.92 out of 5 average rating, 135 reviews

Cottage on Siesta Key Your own getaway!

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

Guest favourite

Guesthouse in Sarasota

4.99 out of 5 average rating, 132 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!