The Best Hotels with a Pool in Osprey, FL from SAR 289 in 2026 | Expedia

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Check availability on Osprey Hotels with a Pool

Tonight

23 May - 24 May

Tomorrow

24 May - 25 May

Next weekend

29 May - 31 May

In two weeks

Our top choices for Osprey hotels with a pool

Premium Pool View King Suite | View from room

Casey Key Resorts - Mainland

Osprey

Splash into sunshine at this Nokomis retreat featuring a heated pool and tiki bar with live music.

SAR 512 total

includes taxes & fees

2 Jun - 3 Jun

Outdoor pool

Englewood Inn & Suites

Englewood South

SAR 336 total

includes taxes & fees

24 May - 25 May

Exterior

Azul Resort Siesta Key

South Village

SAR 641 total

includes taxes & fees

26 May - 27 May

Free daily buffet breakfast

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Nokomis

Escape to a refreshing pool retreat near Venice Beach where outdoor relaxation meets coastal adventure.

SAR 445 total

includes taxes & fees

31 May - 1 Jun

Outdoor pool, pool umbrellas, sun loungers

Cedar Run Resort - Roam Hospitality

South Bradenton

SAR 1,318 total

includes taxes & fees

27 May - 28 May

Outdoor pool, pool umbrellas, sun loungers

Best Western Plus Ambassador Suites Venice

Venice

Dive into poolside perfection with loungers and umbrellas at this Venice retreat.

SAR 435 total

includes taxes & fees

25 May - 26 May

Outdoor pool, a heated pool, sun loungers

Inn at the Beach

Venice Island

Sparkling beachfront pool invites evening dips with stunning sunset views across the water.

SAR 840 total

includes taxes & fees

11 Jun - 12 Jun

Outdoor pool, open 9:00 AM to 6:00 PM, pool umbrellas, sun loungers

Island Sun Inn & Suites - Historic Venice & Beach Getaway

Venice Island

Soak up the sunshine in this inviting pool oasis just minutes from Venice Beach's shores.

SAR 289 total

includes taxes & fees

31 May - 1 Jun

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Choose what matters most at hotels with a pool in Osprey

Breakfast included

Hot tub

Top Osprey Hotel Reviews

Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent

"Great location! Will be back for sure!!"

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

6/10 Okay

"We just stayed for the night, so we didn’t use any of the amenities that the hotel offer, like the pool or breakfast. Our first room had an AC unit that didn’t work great and the room was hot. They moved us to another room upon request, which was nice of them. The next room had working AC, but the hotel card reader on the door needed new batteries, just typical maintenance. The air in the second room did work, but still didn’t cool as much as we wanted it to. The was also an outlet next to a bed that didn’t work. The room was pretty clean, but the bathroom was just ok I’d say. I found a couple hairs but they were in out of the way spots where only I’d check lol. The hotel lobby was very nice, but the building we stayed in looked a little weathered and a not as well maintained in my opinion. Overall, the stay was good, but for the price point I’d expect more upkeep and cleanliness."

Zota Beach Resort

Zota Beach Resort

8/10 Good

"My husband and I enjoyed a visit here for his birthday at Zota resort. I will say that we absolutely loved and enjoyed the resort. The room was perfect, the resort was beautiful and throughout our entire stay we remarked often at how amazing the staff was. Specifically the restaurant staff, they were extremely courteous to us with every interaction and we thought the meals were excellent and well worth the price (notably the breakfast buffet). The gentleman that worked there from near the beginning who assists the waitstaff gave a great history of the hotel which was appreciated. Our favorite day consisted of renting one of the deluxe beach cabanas. We felt the price for how much enjoyment we had was worth every penny. Upon our arrival home we reviewed the receipt of charges and we had noticed that the cabana had cost us a considerable difference than what was quoted at rental. The crew quoted the rental amount and suggested a 20% tip (which we had no issue giving). Our charge however on checkout was much higher. Upon contacting the front desk, she explained the additional charge was another 20% service fee. This was never advised. The end result was removal of the tip as that was the only thing offered (she also advised it was a separate company renting the cabanas and she had no control) This was unnecessary info as we saw it as the resort itself. The overall experience could’ve been perfect had this one incident not taken place."

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

8/10 Good

"We thoroughly enjoyed our stay. We had a few issues with hot water but that was resolved once we brought it up to the desk. My only downfall is that were a little further from the beach. But there is a ride service offered at the hotel so that helped tremendously. We loved the pool and the pizza truck right outside. Super reasonable and delicious"

Lido Beach Resort

Lido Beach Resort

6/10 Okay

"The location is the best part-the beach is beautiful. The pools would have been perfect but they had a bug infestation and did not even try to keep the pool cleaned out with the dead ones or the walkways clean of the dead ones. A simple shop vac in the halls would have helped. The food was very good-tiki bar staff was great. Ordered room service twice from Drift-food was excellent-room service delivery man was super rude and super creepy. Housekeeping staff was friendly but they bang on the door like SWAT and come twice a day which is annoying. Front desk greeters aren’t friendly."

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Frequently asked questions

What are some hotels with pools in Osprey?

Casey Key Resorts - Mainland: Features a snack bar/deli, an outdoor pool, and complimentary wired internet access. Kompose Boutique Hotel: Offers a snack bar/deli, a pool, and complimentary wireless internet access. Golden Host Resort - Sarasota: Provides free self parking, an outdoor pool, and complimentary wireless internet access. Tropical Beach Resorts: Aparthotel, 10-minute walk from Crescent Beach. Features free self parking, an outdoor pool, and complimentary wireless internet access. Spark by Hilton Sarasota Siesta Key Gateway: Hotel located near Siesta Key Beach. Offers daily, an outdoor pool, and free self parking.

What is there to see and do in Osprey?

Explore places like Siesta Key Beach, Venice Beach, and Lido Beach while you're in the area. Make a point to visit attractions like Turtle Beach and Jim Neville Marine Preserve. Osprey appeals to visitors with its beautiful beaches, bar scene, and array of dining options.

When is the best time to book a hotel with a pool in Osprey?

Taking into account the local weather in Osprey 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 Osprey is 44 inches.

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