Osprey Holiday Rentals - Holiday Homes in Osprey

Q: What are some of the best holiday rentals that Osprey has to offer?

Siesta Key Island Rentals : This holiday home rental outside of Osprey comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

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Our top choices for Osprey holiday rentals

Tiny House Siesta

Sarasota

bruno

RM801 total

includes taxes & fees

19 Jul - 20 Jul

Tropical Beach Resorts

South Village

Airida

RM806 total

includes taxes & fees

10 Aug - 11 Aug

Premium bedding, pillow-top beds, iron/ironing board (on request)

A Beach Retreat

Casey Key

Maryna

RM761 total

includes taxes & fees

3 Aug - 4 Aug

Captiva Beach Resort

South Village

Vania

RM828 total

includes taxes & fees

9 Aug - 10 Aug

Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

Sarasota

Lynn

RM626 total

includes taxes & fees

2 Aug - 3 Aug

Siesta Key Island Rentals

Siesta Key

Jason

RM1,690 total

includes taxes & fees

21 Jul - 22 Jul

In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

Siesta Key

Michael

RM1,238 total

includes taxes & fees

19 Jul - 20 Jul

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Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"Place was awesome. I’d definitely be happy to stay here again with my family. Common grounds wasn’t the cleanest and they constantly had a shop vac running for some unknown reason I wasn’t going to ask. But room felt clean and comfortable. Safe was super friendly. Couldn’t have been in a better spot for shopping and going to siesta key."

Siesta Key Palms Resort

8/10 Good

"This resort is a great place to stay! I would definitely recommend it to visitors. Pet friendly, rooms are perfect size. Many locations inside the resorts property to relax. Quiet zones, 2 pools, 2 fire pits. Beaches are close by. A truly fun place to stay. I did mention to owners that the bar was only open 1 of the 3 nights we were there and they explained it was a staffing problem. They are working hard on fixing that issue. It was a tad buggy but it is July in Florida. I would definitely recommend this resort to all"

Tropical Breeze Resort

8/10 Good

"Room was semi clean. Hairs in showers but beds and floors were clean. We stayed 4 nights and did not have house keeping one time. We had to walk to the front desk for fresh towels. The resort did have beach chairs which were great. The front desk was extremely hard to find when arriving. Needs better signs"

The Westin Sarasota

10/10 Excellent

"Great hotel in a walkable location. Awesome view from rooftop bar and pool. Good drinks and menu. Spacious rooms with ample outlets and comfy beds. Mini fridge and closet were useful. Gym looked great but didn't use. Wonderful service-especially when my dad needed a bandaid lol. Helpful to know that parking is valet only. Would stay here again."

Find out more about Osprey

Search for holiday rentals in Osprey on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Osprey using one of the methods below:

View our selection of featured holiday rentals in Osprey
Use the map to find apartments and other holiday homes in the Osprey neighbourhood you prefer
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Look no further and take a look at our great range of rental properties in Osprey!

Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Osprey speak positively about the popular beaches and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

What are some of the best holiday rentals that Osprey has to offer?

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 14 Expedia holiday rentals, you're guaranteed to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Siesta Key Beach and Lido Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.

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