
Vacation rentals with a pool in Downtown, Sarasota
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Downtown, Sarasota
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown, Sarasota rentals with a pool
House rentals with a pool

New Remodeled Pool Put Put Green Mins to Beaches

Lovely Beach Bungalow

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Coastal Comfort Getaway, Heated Pool, Heart of SRQ

LUX Downtown/Siesta Key heated pool & great yard

The Blessing House- Htd Pool/Spa, Close to Beaches

☀Coastal Gem☀Heated pool & amazing location!☀

Downtown Oasis: Poolside Condo, Patio & Gym
Condo rentals with a pool

A&A's Paradise near IMG & Anna Maria beaches

Siesta Key Ground Floor Condo 2BR On Trolley Line

Anchor house +6 min. from Siesta Beach+heated pool

Charming and Updated 1 Bedroom in Runaway Bay

Condo with a View 1: Open Friday, $250/nt!

Siesta Key Beach Front Condo

Near beach. Daily rentals. Pool. king bed

Lido-Key- Tiny Studio Holiday Cottage-A
Quick stats about vacation rentals with a pool in Downtown, Sarasota
Total rentals
30 properties
Nightly prices starting at
G$2,092 GYD before taxes and fees
Total number of reviews
770 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
- Rentals with a washer and dryer Downtown
- Pet-friendly rentals Downtown
- House rentals Downtown
- Apartment rentals Downtown
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- Rentals with a fire pit Downtown
- Rentals with outdoor seating Downtown
- Family-friendly rentals Downtown
- Fitness-friendly rentals Downtown
- Rentals with a patio Downtown
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park