Find Hotels with a Pool in Siesta Key, FL

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Check availability on Siesta Key Hotels with a Pool

Our top choices for Siesta Key hotels with a pool

Outdoor pool, free cabanas
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (300)
"Great spacious room with updated amenities as well as a great white beach and amazing staff! "
United States
Rebecca
The price is ₩621,385
₩777,262 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is ₩384,099
₩515,806 total
includes taxes & fees
Dec 21 - Dec 22
The Inn On Siesta Key
Luxury Suite | Terrace/patio
SeaSpray Resort

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (79)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
The price is ₩456,347
₩515,672 total
includes taxes & fees
Dec 21 - Dec 22
SeaSpray Resort
Outdoor pool, pool umbrellas, sun loungers
Siesta Key Beachside Villas

Siesta Key Beachside Villas

Siesta Key Beachside Villas
2.5 star property
Siesta Key Village
8.8 out of 10, Excellent, (898)
"It checks all the boxes for a beach stay. Great property. One of a shrinking number of Old Sarasota locations that don’t feel like they were built last week from materials found in the “contractor’s specials” section at Home Depot. Would absolutely stay again!"
United States
Martin
Siesta Key Beachside Villas
Condo (Siesta Sands Beach Resort Gulf View) | Exterior
Siesta Sands Beach Resort Gulf View

Siesta Sands Beach Resort Gulf View

Siesta Sands Beach Resort Gulf View
2.5 star property
South Village
10.0 out of 10, Exceptional, (1)
"Loved to property! Clean and accommodating. Had a beautiful ocean view and could walk right out to the beach. Pool area was clean."
United States
Jessica
The price is ₩475,176
₩1,077,539 total
includes taxes & fees
Dec 24 - Dec 25
Siesta Sands Beach Resort Gulf View
2 outdoor pools, pool umbrellas, sun loungers
Tropical Breeze Resort

Tropical Breeze Resort

Tropical Breeze Resort
3.0 star property
Siesta Key Village
9.0 out of 10, Wonderful, (1008)
"Great stay, walking distance to the beach and restaurants! "
United States
Joseph
The price is ₩250,336
₩316,825 total
includes taxes & fees
Dec 21 - Dec 22
Tropical Breeze Resort
Outdoor pool, a heated pool, open open 24 hours, sun loungers
Twin Palms at Siesta

Twin Palms at Siesta

Twin Palms at Siesta
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (577)
"Easy to deal with, we only stayed a night but will be back to the area. Nice little place as we would stay here again. "
United States
Cody
Twin Palms at Siesta
Outdoor pool, free cabanas, pool umbrellas
Turtle Beach Resort

Turtle Beach Resort

Turtle Beach Resort
3.5 star property
Siesta Key
8.8 out of 10, Excellent, (334)
"Great place!!"
United States
Shallynn
Turtle Beach Resort
Outdoor pool, a heated pool
Captiva Beach Resort

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1174)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5156)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is ₩186,733
₩244,338 total
includes taxes & fees
Dec 23 - Dec 24
Tropical Beach Resorts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Siesta Key Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Clean! Right off the beach. New pool is very nice!! A few cute places to walk to for breakfast, lunch and dinner. Will stay here again! "
Alexa 2-night trip
Posted 3 days ago
Tropical Beach Resorts

Frequently asked questions

What's it like visiting Siesta Key?
If taking it easy by the pool is your idea of the perfect getaway, you may want to check out quaint Siesta Key, which offers 16 places to stay with pools. While you're visiting, you can explore attractions like Siesta Key Beach and Lido Beach, and then relax and unwind poolside at one of the accommodations in Siesta Key that guests like for their pools.
What are some hotels with pools in Siesta Key?
Siesta Key Beach Resort and Suites: Resort, 1-minute walk from Siesta Key Beach. Features complimentary bicycles, a pool, and complimentary wireless internet access. Twin Palms at Siesta: Hotel, 4-minute walk from Crescent Beach. Offers free self parking, an outdoor pool, and complimentary wireless internet access. The Capri at Siesta: Hotel, 8-minute walk from Crescent Beach. Provides free self parking, a pool, and sun loungers.
How many hotels with pools will I be able to find in Siesta Key?
Expedia's 16 hotels in Siesta Key give you a great choice for your poolside getaway.
What is there to see and do in Siesta Key?
Explore places like Siesta Key Beach while you're in Siesta Key. The picturesque setting of Crescent Beach and Point of Rocks showcase the area's natural beauty. Visitors to Siesta Key speak highly of the natural attractions, including the beautiful beaches.
When is the best time to book a hotel with a pool in Siesta Key?
Taking into account the local weather in Siesta Key can help you maximize your time at the pool during your trip. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 66°F. Average annual precipitation for Siesta Key is 44 inches.