Search Holiday Rentals in Osprey

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Top Holiday Rentals in Osprey

House | 2 bedrooms, Internet
Charming Florida Beach Home w King Bed Patio

Charming Florida Beach Home w King Bed Patio

2.0 star property
Bay Acres
10.0 out of 10, Exceptional, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
United States
Alyssa
Charming Florida Beach Home w King Bed Patio
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5103)
"The room was clean and the staff was very nice."
United States
Jill
The price is ฿3,842
฿5,076 total
includes taxes & fees
20 Nov - 21 Nov
Tropical Beach Resorts
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
Sarasota
8.6 out of 10, Excellent, (2195)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
Front of property – evening/night
Captiva Beach Resort

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1159)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort
Property amenity
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, (295)
"Loved our stay! "
United States
Michelle
The price is ฿10,887
฿13,954 total
includes taxes & fees
18 Dec - 19 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club
Deluxe Suite, 2 Bedrooms | Living area
SeaSpray Resort

SeaSpray Resort

4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (69)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
The price is ฿8,076
฿9,126 total
includes taxes & fees
30 Nov - 1 Dec
SeaSpray Resort
Front of property
The Ringling Beach House

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (336)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services
Tiny House Siesta

Tiny House Siesta

2.0 star property
Sarasota
8.4 out of 10, Very good, (342)
"Enjoyable stay. "
United States
Lori
The price is ฿3,248
฿7,616 total
includes taxes & fees
20 Nov - 21 Nov
Tiny House Siesta
Exterior
Kon Tiki Inn

Kon Tiki Inn

2.5 star property
Venice Island
10.0 out of 10, Exceptional, (243)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
The price is ฿5,280
฿5,967 total
includes taxes & fees
15 Dec - 16 Dec
Kon Tiki Inn
On the beach, white sand
A Beach Retreat

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (572)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
A Beach Retreat
Exterior
Siesta Key Island Rentals

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (50)
"Very nice place, we loved it. Great location. "
United States
Derrick
Siesta Key Island Rentals
On the beach, white sand
Sea Club I Beach Resort

Sea Club I Beach Resort

3.0 star property
Longboat Key
9.2 out of 10, Wonderful, (331)
"Very nice beach themed bungalow. Loved the quiet and the views. "
United States
Jennifer
Sea Club I Beach Resort
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

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"Great place to stay! "
United States
Carlos
The Inn On Siesta Key
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach

Tropical Villas of Venice Beach

3.5 star property
Venice Island
9.6 out of 10, Exceptional, (239)
"Great Location !!"
United States
Orleys
Tropical Villas of Venice Beach
Garden
Siesta Palms By the Beach

Siesta Palms By the Beach

3.5 star property
South Village
9.4 out of 10, Exceptional, (136)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach
Exterior
Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 star property
Bradenton
7.6 out of 10, Good, (53)
"Perfect place "
United States
chavelys
Bradenton Apartments by Landing
Condo, Pool View | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 star property
Siesta Key
8.4 out of 10, Very good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is ฿4,431
฿11,540 total
includes taxes & fees
25 Nov - 26 Nov
Siesta Heron Suites & Villas
Terrace/patio
Venice Beach Villas

Venice Beach Villas

3.0 star property
Venice Island
9.4 out of 10, Exceptional, (459)
"Always enjoy my stay here as it is close to everything. Friendly and helpful staff."
United States
Alicia
Venice Beach Villas
Property grounds
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
The price is ฿2,557
฿17,479 total
includes taxes & fees
19 Nov - 20 Nov
Chadwick Cove Resort & Marina
Exterior
Paradise Cove at Lemon Bay

Paradise Cove at Lemon Bay

3.5 star property
Olde Englewood Village
8.2 out of 10, Very good, (79)
"Nice, quiet area. Private and had everything we needed! Very nice staff!! "
United States
Deb
Paradise Cove at Lemon Bay
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"I booked for my Grandmas Funeral and I couldn’t have asked for a better experience. The staff are warm and welcoming. The ambience is beautiful and the hotel feels and looks luxurious for a great price. I will definitely book again thank you Julio and Valeria for your service. "
Naomie 2-night trip
Posted 19 hours ago
Kompose Boutique Hotel

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:

  • 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
  • Enter your travel dates to view the best deals on holiday rentals in Osprey while they last

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 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 holiday rentals that Osprey has to offer?

Charming Florida Beach Home w King Bed Patio: This highly rated holiday home rental in Osprey offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 35 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.