Osprey Holiday Rentals - Holiday Homes in Osprey

Q: What are some of the best vacation rentals in Osprey?

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

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Our top choices for Osprey vacation rentals

1. Tropical Beach Resorts

South Village

Margaret Lai Ling

P9,358 total

includes taxes & fees

Aug 27 - Aug 28

2. Tiny House Siesta

Sarasota

Mario

P14,143 total

includes taxes & fees

Sep 19 - Sep 20

3. Siesta Key Island Rentals

Siesta Key

Jason

P20,252 total

includes taxes & fees

Aug 27 - Aug 28

4. Tropical Villas of Venice Beach

Venice Island

Christina

P6,560 total

includes taxes & fees

Aug 27 - Aug 28

5. Captiva Beach Resort

South Village

natalia

P11,539 total

includes taxes & fees

Sep 10 - Sep 11

6. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Justine

P8,873 total

includes taxes & fees

Sep 8 - Sep 9

7. A Beach Retreat

Casey Key

Robert

P12,850 total

includes taxes & fees

Aug 27 - Aug 28

8. SeaSpray Resort

Siesta Key

Isabel

P14,372 total

includes taxes & fees

Sep 1 - Sep 2

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Top Osprey Hotel Reviews

Tropical Beach Resorts

10/10 Excellent

"Clean, close to beach"

Carlisle Inn

10/10 Excellent

"We had a wonderful time at this hotel. The bed and pillows were Marriot quality and great, the breakfast was wonderful. They also had cookies every day from 4-9 pm and hot chocolate. The room looked updated and very clean. AC worked perfectly. No dust anywhere. The best part was the front desk workers. They were always so kind and willing to walk the extra mile to please us. We will use this hotel more often from now on. The Lido Beach was 15 minutes away, and Siesta Keys was 20-25 minutes away. We chose this hotel because it was a good price and it had all if the amenities that we were looking for. No room safe, but we used their safe boxes at the front desk without a problem. One extra perk was the ability to borrow towels, chairs, and umbrela for the beach free of cost. Parking was also plenty at the hotel. We also recommend Libby Restaurant close to Siesta Key. Amazing food at a great price. The shrimp pasta with butter sauce was outstanding and they even gifted us with a chocolate pie that was wonderful."

Siesta Key Palms Resort

10/10 Excellent

"Our stay at Siesta Keys Palm Resort, was simply delightful. From the arrival to the departure, it was smooth sailing. The whole property is clean and well maintained, the hammocks are great and the main pool torches and lighting gives the pool area such a nice vibe. I can’t finish my review without mentioning one of the main reasons I will be returning for another weekend getaway, is the staff, such nice helpful staff. In especially Ana, thank you so very much for your attention and great energy. Hope to be back soon"

Find out more about Osprey

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

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Frequently asked questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors to Osprey speak positively about the popular beaches and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops.

What are some of the best vacation rentals in Osprey?

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

How many vacation rentals are there in Osprey?

With 13 Expedia vacation rentals, you're sure 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 like Siesta Key Beach and Venice Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.

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