Search Vacation Homes in Osprey

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 2987 Vacation Homes in Osprey with updated reviews, rates, and availability.

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals

Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

9.8 out of 10, Exceptional, (11)
"We loved Jennifer Ford. She is an excellent host! Very comfortable beds and hot shower with great water pressure. Everything you need at a fabulous price. We will stay here again! Great location as well!"
Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

9.0 out of 10, Wonderful, (2)
"There is a nice quiet neighborhood to walk around behind one end of the property. We stayed 2 nights and it was very comfortable. Microwave and small refrigerator in the room was good. "
The price is AED 312
AED 634 total
includes taxes & fees
13 Jan - 14 Jan
Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

Private Pool House 6 miles from the Beach

9.8 out of 10, Exceptional, (218)
"Nice house. Very very clean. Owners were quick with response to questions. "
Private Pool House 6 miles from the Beach

Casa Azul 2bed/1bath

9.4 out of 10, Exceptional, (51)
"Great location near everything,Great,beautiful place,peaceful place,great customer service,looking forward to come back soon."
Casa Azul 2bed/1bath

[modern beach bungalow] garden views & patio

10.0 out of 10, Exceptional, (13)
"This property is nestled in a cute, quiet neighborhood and is within a 10 minute walk to the beach/restaurants/entertainment. The washer/dryer was a great amenity after a day at the beach!"
The price is AED 333
AED 1,271 total
includes taxes & fees
13 Jan - 14 Jan
[modern beach bungalow] garden views & patio

Charming Beach Cottage

9.8 out of 10, Exceptional, (15)
"Perfect bnb by the beach"
Charming Beach Cottage

Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

9.6 out of 10, Exceptional, (113)
"We absolutely loved our bungalow and Lisa was the best. Unfortunately hurricane Helene blessed us with a visit. We made the decision to stay since the eye was in the panhandle. Bad decision. Lisa made sure we were safe and moved us to another property on higher ground and made arrangements for us to get off the island the day after. Above and beyond. Thank you for everything!"
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (221)
"Beautiful Villas close to beach and shopping!"
Tropical Villas of Venice Beach

Beachside Retreat with Pool and Beach Access

9.2 out of 10, Wonderful, (32)
"See above "
Beachside Retreat with Pool and Beach Access

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.6 out of 10, Exceptional, (83)
"We stayed for 5 nights and wished we could have stayed longer! The home was perfect for our needs with spacious rooms, clean and well taken care of, and all the amenities we could use. The pool and canal view were added bonuses. The location was especially great for us. We walked daily to the Village to enjoy the variety of restaurants and also the gorgeous public beach. The host was so responsive to questions and also helped us with a forgotten item. Above and beyond! Recommend so...
The price is AED 790
AED 2,006 total
includes taxes & fees
25 Jan - 26 Jan
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

Cozy Studio in Quiet Neighborhood

8.4 out of 10, Very Good, (7)
"Having lived in both Bradenton and SRQ many years I was surprised at both location and size of stay. It was literally a one car garage, completely turned into a vrbo. For a week or less very doable. But for the whole month of Feb. a little too small and inconvenient."
The price is AED 217
AED 609 total
includes taxes & fees
12 Jan - 13 Jan
Cozy Studio in Quiet Neighborhood

Bohemian Sunrise

10.0 out of 10, Exceptional, (76)
"Great place"
Bohemian Sunrise

Cozy Private Room, Close to Siesta Key, Florida

10.0 out of 10, Exceptional, (36)
"Place was beautiful. They have everything you need for your stay. Conveniently located to all the beaches. Will return again if we are ever in the area. Beds and pillows are very comfortable . Patio area is large and everything you need for the beach. Would highly recommend this place ."
Cozy Private Room, Close to Siesta Key, Florida

Mimosa Memories

9.2 out of 10, Wonderful, (13)
"Ryan is extremely responsive. The only issue was WiFi was not working when we arrived but he had someone come by the next morning and resolved it. This was our third stay here and while the neighborhood is mediocre the location is great and the house has been nicely update. Very clean and well appointed. Only other suggestion is phone chargers or plug outlets added to the nightstands by the beds. "
The price is AED 455
AED 1,269 total
includes taxes & fees
18 Jan - 19 Jan
Mimosa Memories

Modern Oasis with Heated Pool near Siesta Key Beach and a Downtown 3BR/@BA

10.0 out of 10, Exceptional, (22)
"This home was clean. In a good neighborhood. When we arrived we noticed that the pool was not filtering, the water level was low and the water was freezing. We reached out to the host. She insisted that it was fine. On Saturday we noticed the outside roof was leaking. Again we reached out to the host. She sent a repairman out. The leak was related to the filtration system. The repairman was at the property Saturday, Sunday and Monday. Eventually replacing the pool pump/filter.He filled the water...
Modern Oasis with Heated Pool near Siesta Key Beach and a Downtown 3BR/@BA

Less than 5 minute walk to Siesta Key Beach.

2.0 star property
10.0 out of 10, Exceptional, (1)
Less than 5 minute walk to Siesta Key Beach.

Pineapples House - POOL private SOUTH facing - HOT TUB-close to BEACHES-walkable

10.0 out of 10, Exceptional, (61)
"This home was cozy and well stocked. On a private street and quiet back yard with several amenities., The host was very attentive and kept us in the loop on everything. I would definitely stay again and highly recommend."
Pineapples House - POOL private SOUTH facing - HOT TUB-close to BEACHES-walkable

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

9.8 out of 10, Exceptional, (92)
"Family of three had a great stay. I would recommend this place to others."
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach

9.2 out of 10, Wonderful, (48)
"My favorite beach is Siesta Key. I decided to spend my birthday weekend there with my husband but wanted to be walking distance to the beach. This place was not only that, but so cute inside. It is also walking distance to the restaurants and shops too."
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach
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.
Don't see what you're looking for?
See all available properties in Osprey
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Osprey

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
The price is AED 534
AED 686 total
includes taxes & fees
13 Jan - 14 Jan
Tropical Beach Resorts

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (220)
"Very lovely (and large!) accommodation. Extremely clean. Front desk staff kind of rude/pretentious.Great location right on the beach at Siesta Key. Heated pool with good poolside bar. Also had a hot tub, which was nice as the weather was a bit cool when we were there. Feel like I was misled a bit based on room description--thought we were booking a room with beach view, but instead got "city view"--which essentially looked into a back alley and at a 7-eleven. For the price/my personal budget,...
The price is AED 1,875
AED 2,305 total
includes taxes & fees
28 Jan - 29 Jan
The Residences at Siesta Key Beach by Hyatt Vacation Club

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2085)
"The room was so neat and would definitely recommend anyone needing a one nights stay!! We had a great time! "
The price is AED 579
AED 654 total
includes taxes & fees
20 Jan - 21 Jan
Hibiscus Suites - Gateway to Siesta Key
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.