The Best Osprey Hotels with Pools from $76 - Hotels with indoor pools in Osprey, FL

A marina with docked boats, a wooden bridge, and a building with a red roof.

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Our top choices for Osprey hotels with a pool

Premium Pool View King Suite | View from room

Premium Pool View Double Queen | Balcony view

1. Casey Key Resorts - Mainland

Osprey

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

$118 nightly

$133 total

Aug 23 - Aug 24

Total with taxes and fees

Premium bedding, in-room safe, desk, laptop workspace

2. Holiday Inn Express Sarasota East - I-75 by IHG

Sarasota

Dive into refreshing bliss at this beachside haven with a sparkling outdoor pool and hot tub sanctuary.

$84 nightly

$95 total

Aug 16 - Aug 17

Total with taxes and fees

Premium bedding, pillowtop beds, in-room safe, desk

3. Comfort Suites Sarasota - Siesta Key

Sarasota

Plunge into poolside paradise with soothing hot tub escapes at this Sarasota retreat.

$91 nightly

$103 total

Aug 27 - Aug 28

Total with taxes and fees

Outdoor pool, pool umbrellas, sun loungers

4. Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

Splash into vacation mode with a sparkling poolside sanctuary just steps from Siesta Key Beach.

$98 nightly

$110 total

Aug 30 - Aug 31

Total with taxes and fees

Standard Room, 1 King Bed, Non Smoking | In-room safe, laptop workspace, blackout drapes, iron/ironing board

5. Quality Inn - Near Serenoa Golf Club

Sarasota

Splash into fun at this hotel's sunlit outdoor pool just minutes from Siesta Key Beach.

$67 nightly

$76 total

Aug 13 - Aug 14

Total with taxes and fees

Siesta Suite (1 Queen Bed and 1 Sofabed) | Premium bedding, pillowtop beds, in-room safe, blackout drapes

6. Siesta Key Palms Resort

Sarasota

Dive into paradise with two sparkling outdoor pools surrounded by lush gardens, just a short walk from Crescent Beach.

$149 nightly

$169 total

Aug 18 - Aug 19

Total with taxes and fees

Free toiletries, hair dryer, towels, soap

7. 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.

$103 nightly

$116 total

Sep 6 - Sep 7

Total with taxes and fees

8. Days Inn by Wyndham Sarasota I-75

Sarasota

Splash into Florida sunshine at this Sarasota hotel with a serene poolside escape just minutes from Siesta Key Beach.

$68 nightly

$76 total

Aug 9 - Aug 10

Total with taxes and fees

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Choose what matters most at hotels with a pool in Osprey

Breakfast included

Hot tub

4 stars

Beach

5 stars

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

10/10 Excellent

"On the beach and conveniently located. Nostalgic."

Siesta Key Beach Resort and Suites

10/10 Excellent

"We had an amazing stay! We came from the east coast of Florida and our friends from Texas flew in and met us there. Between us all we rented four rooms over looking the lounge. The rooms were beautiful and comfortable. The staff was amazing! Estephanie was extremely helpful and accommodating and Joey in the lounge was great at taking care of our party of seven every day. We will definitely be back!"

Aloft by Marriott Sarasota

10/10 Excellent

"Our breakfast was included for an additional fee, I will say that it will make a difference to serve a bigger portion of fruit 4oz cup instead of 2oz or add a fruit bar or a parfait yogurt bar. The portion is small, for me was ok, but for my 15 year old son or husband was a small portion."

Zota Beach Resort

10/10 Excellent

"We stayed for just one night and we loved it. We traveled with our two mini dachshunds and it was great. Room was clean and comfy, food was good (burger was awesome) and bartenders were great. We’d absolutely come back."

The Westin Sarasota

10/10 Excellent

"Clean room, quiet ane peaceful"

Inn at the Beach

10/10 Excellent

"Quick overnight trip. Hotel waa perfect! Pool, hot tub, breakfast. Everything we needed to make it perfect"

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"We loved our stay. The hotel is only less than 10min drive to the beach The pool with a bar was a big plus for us, after 3 hours driving! Lol The hotel is clean, the breakfast is nothing too much but was good - I missed cheese, ham, bacon and milk, for example, but it wasn't a big deal. The room is very clean, but the curtains didn't covers the windows very well and for me (light sleeper) the room wasn't dark enough and I had some trouble to sleep, ai had to put a face towel on my face to be able to sleep... The shower is very weak and this was a head ache to wash my hair (I have a big and lot of hair!). And, the room didn't have a microwave or soap at the sink - didn't understand why! Overall, is worth the money and it is a good stay."

Tropical Beach Resorts

10/10 Excellent

"Such a lovely resort, a stone’s throw from the beach and close to shops and bars. Lovely clean room. And free parking"

The Ritz-Carlton, Sarasota

10/10 Excellent

"Our stay at The Ritz-Carlton Sarasota was absolutely amazing! From the moment we arrived, the staff made us feel welcome with their exceptional hospitality and attention to detail. Everyone was friendly, professional, and went above and beyond to ensure our stay was perfect. The hotel was spotless, with beautifully maintained spaces that made the stay even more relaxing and enjoyable. The food was delicious, with excellent quality, presentation, and flavor at every meal. We highly recommend Jack Dusty. Overall, it was an unforgettable experience, and I highly recommend The Ritz-Carlton Sarasota for luxury, comfort, and world-class service. We can’t wait to return!"

Frequently asked questions

What are the best hotels in Osprey with outdoor pools?

Casey Key Resorts - Mainland is a fantastic option for travellers seeking a hotel in Osprey with an inviting outdoor pool. Rated 8.8 by guests, this resort creates an inviting space with its friendly and amazing staff, ensuring that travellers feel right at home.The outdoor pool is complemented by delightful amenities such as poolside cabanas that are available for free, making it a superb spot to relax and soak up the sun. Guests particularly appreciate the spacious and clean rooms, along with the excellent food offerings available on-site. The location is another highlight, providing easy access to nearby attractions that enhance your Osprey experience.For families, the pool area offers sun loungers, allowing you to unwind while the kids enjoy splashing around.

How much does a hotel with outdoor pool in Osprey cost?

Enjoy staying in a hotel in Osprey with an outdoor pool. You can find a great deal from $76 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

Are there hotels in Osprey with outdoor pool cabanas or loungers?

Casey Key Resorts - Mainland is an excellent choice for travellers seeking outdoor relaxation in Osprey. With an excellent review rating of 8.8, this hotel offers a delightful atmosphere complemented by its inviting outdoor pool, complete with free poolside cabanas and sun loungers—superb for lounging in the Florida sun.Guests rave about the friendly and amazing staff, who go above and beyond to ensure a pleasant stay. The clean and spacious rooms are designed for comfort, making it a great option for families or those traveling with children. Additionally, the hotel features a poolside bar, allowing you to sip refreshing drinks without leaving your comfortable spot by the water.For those looking to enjoy some quality time outdoors, Casey Key Resorts - Mainland provides the ideal setting, blending convenience with a laid-back, family-friendly environment.

Which Osprey hotels offer poolside service for food and drinks?

Casey Key Resorts - Mainland is a fantastic choice for travellers seeking a delightful poolside experience in Osprey. With an impressive traveller rating of 8.8, guests rave about the friendly and amazing staff, as well as the clean and spacious rooms that ensure a comfortable stay.This hotel features an inviting outdoor pool, complete with a Poolside Bar where you can sip on refreshing drinks while enjoying the sun. Pool cabanas are available for free, offering a great spot to relax with family or friends. Sun loungers around the pool create a laid-back atmosphere, making it easy to unwind after a day of adventure.Families will appreciate the excellent food options available, enhancing the overall experience.

Is it cheaper to book flights and a Osprey hotel with a pool as a package?

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.

Can I cancel my hotel reservation on Expedia?

Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Osprey for you.

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Check availability on Osprey Hotels with a Pool

Our top choices for Osprey hotels with a pool

1. Casey Key Resorts - Mainland

2. Holiday Inn Express Sarasota East - I-75 by IHG

3. Comfort Suites Sarasota - Siesta Key

4. Spark by Hilton Sarasota Siesta Key Gateway

5. Quality Inn - Near Serenoa Golf Club

6. Siesta Key Palms Resort

7. Holiday Inn Express & Suites Nokomis Sarasota South by IHG

8. Days Inn by Wyndham Sarasota I-75

9. Hampton Inn & Suites Venice Bayside South Sarasota

10. Tropical Beach Resorts

Choose what matters most at hotels with a pool in Osprey

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

Siesta Key Beach Resort and Suites

Aloft by Marriott Sarasota

Zota Beach Resort

The Westin Sarasota

Inn at the Beach

Spark by Hilton Sarasota Siesta Key Gateway

Tropical Beach Resorts

The Ritz-Carlton, Sarasota

Frequently asked questions

Explore a world of travel with Expedia

Find Hotels with a Pool in Osprey, FL

Upfront pricing

Treat yourself

Be picky

Check availability on Osprey Hotels with a Pool

Our top choices for Osprey hotels with a pool

1. Casey Key Resorts - Mainland

2. Holiday Inn Express Sarasota East - I-75 by IHG

3. Comfort Suites Sarasota - Siesta Key

4. Spark by Hilton Sarasota Siesta Key Gateway

5. Quality Inn - Near Serenoa Golf Club

6. Siesta Key Palms Resort

7. Holiday Inn Express & Suites Nokomis Sarasota South by IHG

8. Days Inn by Wyndham Sarasota I-75

9. Hampton Inn & Suites Venice Bayside South Sarasota

10. Tropical Beach Resorts

Choose what matters most at hotels with a pool in Osprey

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

Siesta Key Beach Resort and Suites

Aloft by Marriott Sarasota

Zota Beach Resort

The Westin Sarasota

Inn at the Beach

Spark by Hilton Sarasota Siesta Key Gateway

Tropical Beach Resorts

The Ritz-Carlton, Sarasota

Frequently asked questions

Explore a world of travel with Expedia