Osprey Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Osprey holiday rentals

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

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

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5156)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is S$214
includes taxes & fees
25 Dec - 26 Dec
Tropical Beach Resorts
Front of property – evening/night
Captiva Beach Resort

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1174)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort
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

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2213)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
Living area
SeaSpray Resort

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (79)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
The price is S$451
includes taxes & fees
21 Dec - 22 Dec
SeaSpray Resort
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

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, (300)
"Great spacious room with updated amenities as well as a great white beach and amazing staff! "
United States
Rebecca
The price is S$648
includes taxes & fees
19 Jan - 20 Jan, 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
Front of property
The Ringling Beach House

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (345)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House
Living area
Tiny House Siesta

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is S$320
includes taxes & fees
21 Dec - 22 Dec
Tiny House Siesta
Exterior
Kon Tiki Inn

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (246)
"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
Kon Tiki Inn
Exterior
Siesta Key Island Rentals

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (54)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is S$440
includes taxes & fees
20 Dec - 21 Dec
Siesta Key Island Rentals
On the beach, white sand
A Beach Retreat

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (577)
"Great location, recent updates"
United States
Michael
A Beach Retreat
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

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is S$441
includes taxes & fees
21 Dec - 22 Dec
The Inn On Siesta Key
Garden
Siesta Palms By the Beach

Siesta Palms By the Beach

Siesta Palms By the Beach
3.5 star property
South Village
9.4 out of 10, Exceptional, (137)
"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
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach

Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (241)
"Clean, but very outdated. "
United States
Tim
Tropical Villas of Venice Beach
Private kitchen
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is S$466
includes taxes & fees
20 Dec - 21 Dec
Siesta Heron Suites & Villas
On the beach, white sand
Sea Club I Beach Resort

Sea Club I Beach Resort

Sea Club I Beach Resort
3.0 star property
Longboat Key
9.2 out of 10, Wonderful, (335)
"Very nice beach themed bungalow. Loved the quiet and the views. "
United States
Jennifer
Sea Club I Beach Resort
Terrace/patio
Venice Beach Villas

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (469)
"Everything was on point. "
United States
Adalid
Venice Beach Villas
Exterior
Bradenton Apartments by Landing

Bradenton Apartments by Landing

Bradenton Apartments by Landing
4.5 star property
Bradenton
7.4 out of 10, Good, (55)
"Perfect place "
United States
chavelys
Bradenton Apartments by Landing
Property grounds
Chadwick Cove Resort & Marina

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 S$727
includes taxes & fees
21 Dec - 22 Dec
Chadwick Cove Resort & Marina
Exterior
Paradise Cove at Lemon Bay

Paradise Cove at Lemon Bay

Paradise Cove at Lemon Bay
3.5 star property
Olde Englewood Village
8.2 out of 10, Very good, (81)
"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.
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Top Osprey Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Overall, excellent experience the hallways on the floor is the lighting is so cool and modern. In the room is spacious, modern, very nice looking. I had an excellent experience."
Maura 1-night trip
Posted 1 day ago
Kompose Boutique Hotel

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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 20 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.