Siesta Key Vacation Rentals with Pools

13 places to stay · Ad disclosure

All 56Hotels & Resorts 8Condos 31Vacation Homes 17Beachfront 1Ocean View 3Pool 13Hot Tub 2Pet friendly 1Large groups (4+ BR) 2Under $150 2Rated 4.5+ 34

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Siesta Key Vacation Rentals with Pools

We list 13 Siesta Key vacation rentals with pools, about 23% of the places to stay we compare in Siesta Key. Nightly prices start at $154, and the typical stay is about $338 a night. They range from 1 to 3 bedrooms. They book on Trip.com, and the list above puts their stays side by side so you can compare photos, ratings and prices first.

Siesta Key Vacation Rentals with Pools FAQ

How much do Siesta Key vacation rentals with pools cost?

From $154 a night, and about $338 for a typical stay. These are sample rates for the dates on each stay; open a deal with your dates for the exact price, including fees and taxes.

How many Siesta Key vacation rentals with pools are there?

We compare 13 of them in Siesta Key right now. Add your dates above to see which are free when you want to go.

What else do Siesta Key vacation rentals with pools have?

Of these stays, 2 have a hot tub. Combine the filters above to narrow them down.

What should I check before booking?

Some pools are private and heated indoors, others are a shared resort pool that’s only open in summer. Check the listing for which kind it is and when it’s open.

How do I book?

Pick a stay and choose View Deal. You book directly on Trip.com, which handles payment, confirmation and support. 41 Vacations doesn’t charge you anything; we may earn a commission from the partner.

About Siesta Key

Siesta Key, just off Sarasota on Florida’s Gulf coast, is famous for its powdery white quartz sand that stays cool underfoot and its calm, clear water. Most places to stay are condos and vacation rentals, many within walking distance of the beach.
Where to stay

Siesta Key Village, near the main public beach, has restaurants, bars and shops within walking distance.
Crescent Beach and the south end, around Point of Rocks and Turtle Beach, are quieter, with condos and rentals near calmer water good for snorkeling.

Best times to visit

Best overall: April through May and late October through November: warm, sunny and less crowded than winter.
Best value: Late summer through early fall, when rates drop and the beach is quieter.
Busiest: February through April, plus summer holidays.
Weather to know: Summer afternoons bring thunderstorms and the occasional red tide. Hurricane season runs June through November.

Getting there
Sarasota Bradenton International Airport (SRQ) is about 25 minutes away. Tampa International (TPA) is roughly an hour.
Tips for booking
Many Siesta Key rentals have minimum stays and cleaning fees, so compare the total price for your dates, not just the nightly rate.

Flying in? Compare flights on CheapOAir

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