Osprey Vacation Rentals

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Check prices for these dates

Tonight
Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Osprey vacation rentals

Beach towels
Charming Osprey Home

Vacation Home in Bay Acres

Charming Osprey Home
2.0 star property
The price is ￥30,719
￥58,354 total
includes taxes & fees
Dec 29 - Dec 30
Charming Osprey Home
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services
Tiny House Siesta

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very Good, (346)
"Enjoyable stay. "
United States
Lori
The price is ￥16,393
￥37,547 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Tiny House Siesta
Exterior
#3 Small house walking distance to Warm Mineral Spring

Cottage in Warm Mineral Springs

#3 Small house walking distance to Warm Mineral Spring
9.0 out of 10, Wonderful, (9)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
The price is ￥10,177
￥25,247 total
includes taxes & fees
Dec 29 - Dec 30
#3 Small house walking distance to Warm Mineral Spring
Property grounds
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5182)
"Great location, value, clean, friendly staff. Will definitely stay there again. "
United States
JoAnna
The price is ￥22,491
￥28,954 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tropical Beach Resorts
Fridge, microwave, stovetop, coffee/tea maker
Charming cottage for 2 across warm mineral springs park

Cottage in Warm Mineral Springs

Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (10)
"Property was perfect for the price."
United States
William M.
The price is ￥11,743
￥27,016 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming cottage for 2 across warm mineral springs park
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Vacation Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
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 ￥28,837
￥64,078 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Siesta Heron Suites & Villas
Exterior
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (248)
"Lovely decor, very clean"
United States
Frederick
The price is ￥41,201
￥46,557 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Kon Tiki Inn
Property grounds
Chadwick Cove Resort & Marina

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
The price is ￥13,300
￥85,352 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Chadwick Cove Resort & Marina
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Sarasota

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2221)
"Very nice place !"
United States
Ivette
Hibiscus Suites - Gateway to Siesta Key
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (302)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is ￥62,002
￥78,024 total
includes taxes & fees
Jan 27 - Jan 28, 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
Fridge, microwave, oven, stovetop
Mimosa Memories

Vacation Home in South Venice

Mimosa Memories
9.4 out of 10, Exceptional, (30)
"Nice quiet home , very clean. "
United States
David M.
The price is ￥17,755
￥51,923 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Mimosa Memories
Beach
Newly renovated only minutes away from the beach!!

Apartment in Olde Englewood Village

Newly renovated only minutes away from the beach!!
9.6 out of 10, Exceptional, (58)
"Clean, comfortable, everything you need! Owner is great!"
United States
Cheryl L.
The price is ￥19,571
￥44,661 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Newly renovated only minutes away from the beach!!
Fridge, microwave, coffee/tea maker, dining tables
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Apartment in Bayshore Gardens

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
9.2 out of 10, Wonderful, (36)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
The price is ￥11,743
￥27,016 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
On the beach, sun loungers, beach towels
Direct Beachfront 2BR Cottage on Casey Key!

Cottage in Casey Key

Direct Beachfront 2BR Cottage on Casey Key!
9.2 out of 10, Wonderful, (69)
"The Cottage is simple and in need of a few updates, but it is a beach cottage and the salt air is not kind. Overall, the location is fantastic, the Cottage is clean and comfortable and our stay was great."
United States
Bob T.
The price is ￥26,304
￥68,302 total
includes taxes & fees
Dec 29 - Dec 30
Direct Beachfront 2BR Cottage on Casey Key!
Indoor pool
Venice Dove Shell

Vacation Home in Venice East

Venice Dove Shell
2.0 star property
The price is ￥22,703
￥28,786 total
includes taxes & fees
Dec 29 - Dec 30
Venice Dove Shell
Fridge, microwave, oven, stovetop
Myakka River

Vacation Home in Venice

Myakka River
9.8 out of 10, Exceptional, (18)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is ￥28,965
￥71,466 total
includes taxes & fees
Dec 29 - Dec 30
Myakka River
Fridge, microwave, coffee/tea maker, electric kettle
Beautiful University Pines Studio in Sarasota

Apartment in Sarasota

Beautiful University Pines Studio in Sarasota
9.8 out of 10, Exceptional, (35)
"Super clean rental… exactly as described, great location close to everything"
United States
Randy S.
The price is ￥14,874
￥31,752 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Beautiful University Pines Studio in Sarasota
On the beach, white sand
A Beach Retreat

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (580)
"Great location, recent updates"
United States
Michael
A Beach Retreat
Sun loungers, beach towels
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Cottage in South Village

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.6 out of 10, Exceptional, (81)
"We loved our stay at the Drift Inn. Very clean, just the right amount of room for 4, easy access to the beach and pool. The beds were very comfortable. The owner was very quick to respond to questions from beginning to end. We would stay here again."
United States
Kimberly P.
The price is ￥19,571
￥51,269 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Terrace/patio
Lakeview Bradenton Rental Near Beaches & IMG

Vacation Home in South Bradenton

Lakeview Bradenton Rental Near Beaches & IMG
The price is ￥17,591
￥39,292 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Lakeview Bradenton Rental Near Beaches & IMG
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
"Great staff. Clean rooms and hotel. Good Breakfast. Good amenities. The weird part was the bathrooms but it was managable"
prashant 1-night trip
Posted 1 day 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:

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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?

Charming Florida Beach Home w King Bed Patio: Visitors give good reviews to this Osprey vacation home rental, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 20 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 Lido 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.