Vacation rentals with a pool in Sarasota Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sarasota Beach

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

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Guest favorite

Apartment in Siesta Key

4.99 out of 5 average rating, 142 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Beautiful Apartment w/ Hotel Services, at Siesta Key Beach. Totally remodeled. Fully equipped to spend the best holidays with family or friends. Condo hotel, on the best beach in Siesta. 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 600 MB Wifi. HD TV. 70” Smart TV Nesspreso, Keurig Machines

Dec 11 – 18

ﺩ.ﺇ1,664 per night

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 286 reviews

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *COVID Cleaning. SELF CHECK IN. Non shared Pool. Bungalow w/private entrance & patio. Designers Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Key Beach, shops, dining, & 5mins/Downtown Sarasota core. Walk to 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!

Oct 13 – 20

ﺩ.ﺇ675 per night

Guest favorite

Guest suite in Sarasota

4.89 out of 5 average rating, 110 reviews

Downtown privacy, beaches and nightlife all around

For the couple (or individual) who wants a fabulous private home and is in a centrally-located space in downtown Sarasota. Where the beaches meet the nightlife (Legacy Trail is 5 short blocks away, pickle ball 3 and Robarts Arena 2), this separate In-Law Suite has its own entrance, private patio and lots of space (1,000 sq. feet). 2 bikes and beach items for use are: chairs, umbrellas, noodles and coolers. The washer/dryer is attached, high-speed internet/cable; there is a gas grill, 2 tvs

Jul 19 – 26

ﺩ.ﺇ460 per night

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Nov 3 – 10

ﺩ.ﺇ2,315 per night

Superhost

Condo in Siesta Key

4.83 out of 5 average rating, 238 reviews

Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks

We pay your AIRBNB service fees for you! Updated & inviting coastal getaway, located on the island of Siesta Key in a small resort called Solitude Suites on Siesta Key. The “Sunset Suite” has a living/dining/kitchenette area w/ 65” TV, a separate bedroom & a separate bathroom. Off the bedroom is a private open wood deck. Table & chairs allow you to enjoy the perfect view of a Siesta Key sunset. New shower in Dec 2023! 2 min drive or 10 min walk to beach! Enjoy FREE Kayaks, SUPs & Tiki Huts!

ﺩ.ﺇ561 per night

Guest favorite

Apartment in Sarasota

4.96 out of 5 average rating, 207 reviews

Private 2 Bedroom Suite with Kitchenette

A lovely private suite, attached to our home, consisting of 2 bedrooms, bath, and kitchenette/dining area. Features a private entrance and use of our family pool, lanai & sauna. Located close to I75, and minutes away from Nathan Benderson Park, and the Mall at University Town Center where you'll find many shopping & eating options. You will also be only 12 miles from the beautiful white sand beach of Siesta Key with all of the activities it affords. Located in a family friendly neighborhood.

Jun 15 – 20

ﺩ.ﺇ489 per night

Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 276 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.

Feb 26 – Mar 5

ﺩ.ﺇ1,681 per night

Guest favorite

Guesthouse in Sarasota

5.0 out of 5 average rating, 102 reviews

Magical Guesthouse 1 mi from SRQ airport

Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Nov 16 – 23

ﺩ.ﺇ499 per night

Guest favorite

Guesthouse in Sarasota

4.99 out of 5 average rating, 131 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!

Jul 13 – 20

ﺩ.ﺇ528 per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 188 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Jul 17 – 24

ﺩ.ﺇ416 per night

Guest favorite

Home in Siesta Key

5.0 out of 5 average rating, 125 reviews

One-of-a-kind*Beach, Village, Dock & Private Pool!

HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time. If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

Jul 14 – 21

ﺩ.ﺇ2,600 per night

Guest favorite

Condo in Siesta Key

4.93 out of 5 average rating, 181 reviews

Siesta key getaway!

perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !

Jul 4 – 11

ﺩ.ﺇ545 per night