Vacation rentals with a pool in Sarasota

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sarasota

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

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 279 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!

Jul 18 – 25

$150 per night
Guest favorite

Guest suite in Sarasota

4.89 out of 5 average rating, 107 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

May 4 – 11

$119 per night
Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 298 reviews

*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*

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!

Jan 22 – 29

$513 per night

Popular amenities for Sarasota rentals with a pool

House rentals with a pool

Superhost

Home in Sarasota

4.83 out of 5 average rating, 105 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

Nov 8 – 15

$143 per night
Guest favorite

Home in Sarasota

4.94 out of 5 average rating, 143 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Sep 2 – 9

$400 per night
Guest favorite

Home in Sarasota

4.94 out of 5 average rating, 292 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

Jun 30 – Jul 7

$252 per night
Guest favorite

Home in Sarasota

4.97 out of 5 average rating, 157 reviews

The Palms-Private Heated Pool Hot Tub-5mi to beach

Apr 30 – May 7

$251 per night
Guest favorite

Home in Sarasota

4.97 out of 5 average rating, 201 reviews

Your private retreat near Siesta Key Beach.

Sep 17 – 24

$289 per night
Guest favorite

Home in Sarasota

4.97 out of 5 average rating, 118 reviews

La Hacienda / heated pool, hot tub, 6mi to beach

Jul 23 – 30

$364 per night
Superhost

Home in Sarasota

4.94 out of 5 average rating, 115 reviews

White Sands Villa - Heated Pool/Spa - Near Beaches

Aug 29 – Sep 5

$248 per night
Guest favorite

Home in Sarasota

4.97 out of 5 average rating, 113 reviews

Siesta Key Escape 3 BR/2BA Heated Pool House

Aug 6 – 13

$263 per night
Guest favorite

Home in Sarasota

4.89 out of 5 average rating, 123 reviews

Cottage On Bay (private backyard, near beaches)

Jun 7 – 14

$239 per night
Guest favorite

Home in Bradenton

4.91 out of 5 average rating, 251 reviews

Palm Retreat Gold: Luxury Edition of #1 Rental

Dec 5 – 12

$253 per night
Guest favorite

Home in Sarasota

4.97 out of 5 average rating, 106 reviews

Gorgeous Home / Heated Pool and Spa

Dec 12 – 19

$281 per night
Guest favorite

Home in Sarasota

4.93 out of 5 average rating, 102 reviews

Lake Front House with a Pool

Sep 27 – Oct 4

$184 per night

Condo rentals with a pool

Guest favorite

Condo in St. Pete Beach

4.92 out of 5 average rating, 200 reviews

Sunset Beach Condo in Treasure Island

Sep 13 – 20

$111 per night
Guest favorite

Condo in Sarasota

4.95 out of 5 average rating, 120 reviews

Cozy Beach Side 1BD/2BA, Walk to Beach & Pool

Sep 18 – 25

$169 per night
Guest favorite

Condo in Longboat Key

4.97 out of 5 average rating, 146 reviews

Sunset Studio on the Coast

Nov 30 – Dec 7

$275 per night
Guest favorite

Condo in Bradenton

4.98 out of 5 average rating, 167 reviews

Shorewalk full condo IMG Beaches Anna Maria

Aug 31 – Sep 7

$126 per night
Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 267 reviews

On the Beach; Siesta Key SunBum Studio

Jan 1 – 8

$390 per night
Guest favorite

Condo in Siesta Key

4.83 out of 5 average rating, 187 reviews

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

Jul 26 – Aug 2

$150 per night
Guest favorite

Condo in Siesta Key

4.85 out of 5 average rating, 130 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

Nov 4 – 11

$141 per night
Guest favorite

Condo in Ruskin

4.93 out of 5 average rating, 106 reviews

Beach Condo with water view!

Jun 23 – 30

$95 per night
Guest favorite

Condo in Englewood

4.93 out of 5 average rating, 110 reviews

Immaculate Ground Floor Beach Studio on the Gulf

Aug 2 – 9

$144 per night
Guest favorite

Condo in Sarasota

4.91 out of 5 average rating, 214 reviews

New Renovation! Walk to Beach, Pool, Restaurants!

Aug 15 – 22

$175 per night
Guest favorite

Condo in Longboat Key

4.93 out of 5 average rating, 143 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Nov 21 – 28

$268 per night
Guest favorite

Condo in Bradenton

4.94 out of 5 average rating, 125 reviews

The Seashell Cottage with peaceful water views!

Nov 16 – 23

$142 per night

Quick stats about vacation rentals with a pool in Sarasota

Total rentals

880 properties

Rentals with dedicated workspaces

520 properties have a dedicated workspace

Pet-friendly rentals

320 properties allow pets

Family-friendly rentals

680 properties are a good fit for families

Total number of reviews

22K reviews

Nightly prices starting at

$10 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Sarasota
  6. Rentals with pools