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 2710 Vacation Homes in Osprey with updated reviews, rates, and availability.

Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, (192)
"The villa is well situated, being close to shopping, transport, and the tourist sites. We would definitely stay there again. The room have everything chair beach towels bikes kitchen staff love the place these was my second time Es un excelente lugar para gente mayor muy tranquilo aburrido para jóvenes .el room cuenta con todo es muy limpio y cómodo casa room tiene un patio con Barbie q hay bicicletas y el supermercado queda a 5 min lo mismo el centro "
Tropical Villas of Venice Beach
Siesta Key Island Rentals
3.0 star property
10.0 out of 10, Exceptional, (12)
"15 minute or less walk to everything you need. "
Siesta Key Island Rentals
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very Good, (26)
"I like everything, thank you so much!!!"
The price is AED 463
AED 1,511 total
includes taxes & fees
12 Jun - 13 Jun
Siesta Heron Suites & Villas
Save an average of 15% on thousands of hotels when you're signed in
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
9.8 out of 10, Exceptional, (69)
"We booked this trip for our buddies wedding. The property was quiet and well maintained. We enjoyed our stay!"
The price is AED 1,084
AED 2,430 total
includes taxes & fees
20 Jun - 21 Jun
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Steps From Beach. Private entrance.
9.8 out of 10, Exceptional, (73)
"We had a great time, place was nice, so close to the beach, provided everything we needed for spending a weekend at the beach. We will definitely be back! Thanks so much for letting us stay at your place!"
Steps From Beach. Private entrance.
Chic Downtown Gem - The Cocoanut Hut, newly constructed
9.8 out of 10, Exceptional, (12)
"The hosts thought of everything. It’s super new and clean with comfy beds, great shower pressure, and you are located close to everything. It is safe and really comfortable. We would stay here again."
Chic Downtown Gem - The Cocoanut Hut, newly constructed
Retreat Half-Mile to Beach/Siesta Key Village
8.8 out of 10, Excellent, (25)
"Overall great experience. Home was close enough to the Siesta Village that we could walk. Close to market and trolley. Quiet neighborhood. House was clean and comfortable."
Retreat Half-Mile to Beach/Siesta Key Village
Private Beach and Incredible Sunsets-Exquisite Home
10.0 out of 10, Exceptional, (3)
"We had an incredible time! Andrew was super responsive and helpful."
Private Beach and Incredible Sunsets-Exquisite Home
4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool -
10.0 out of 10, Exceptional, (165)
"This is our second trip to sea palm cottages in the last 8 months. The house is comfortable, the decor is lovely and the owners are delightful to work with. The pool is a backyard oasis and is an easy walk to white sand beaches and downtown restaurants and shops. We are already planning our next visit back!"
4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool -
Modern near Siesta Beach
9.8 out of 10, Exceptional, (30)
"We had the best time at this property! It was very clean, serene with all of the beautiful landscaping surrounding the property and pool and loved the modern amenities. It is a short drive to everything in Sarasota. They are very responsive and helpful when there is an issue. I would highly recommend any family to stay here."
Modern near Siesta Beach
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
9.6 out of 10, Exceptional, (100)
"This cottage is just steps away from the beach and Siesta Village with many restaurants, shops, and the market. You can park your car and never move it until check out. The cottage’s terrace was perfect for morning and nights. Everything was clean and neat. They have beach chairs (5 Tommy Bahama chairs), a cooler, beach cart, umbrella, and more. Keurig and drip coffee, everything we needed for the kitchen and plenty of paper supplies. We would definitely stay again."
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Pool, Hot tub, Close to Beaches, Shopping, More!
9.6 out of 10, Exceptional, (12)
"Loved everything about this home. Had a few very minor issues but all were handled very quickly. We will be booking again!"
Pool, Hot tub, Close to Beaches, Shopping, More!
Bay House Retreat managed by Beach Retreats
9.8 out of 10, Exceptional, (42)
"Our stay which included teens, parents, grandparents and a friend was amazing! The house is perfect for our group of all ages…even better than the listing as you can never fully capture a gorgeous view in a photograph! The pool, fishing dock and pontoon boat rental made our stay adventure packed. The house is beautifully decorated and spacious for larger groups. The owner kindly extended our check-out time as we had a later flight and recommended some great places to eat. We all would absolutely...
Bay House Retreat managed by Beach Retreats
Sarasota-Indian Beach Zen Home (private-pet friendly)
9.8 out of 10, Exceptional, (14)
"We love the home. It was clean and perfect for us with our Labrador. Good location, close to beaches and main street. Great restaurants close by and we walked down two blocks to each the sunset. Will definitely come back."
Sarasota-Indian Beach Zen Home (private-pet friendly)
Cozy beach getaway! Close to Siesta Key Beach! Pet Friendly!
8.8 out of 10, Excellent, (19)
"Perfect"
The price is AED 735
AED 1,162 total
includes taxes & fees
2 Jul - 3 Jul
Cozy beach getaway! Close to Siesta Key Beach! Pet Friendly!
Beach house
10.0 out of 10, Exceptional, (22)
"This an amazing beach get away! We loved every minute in this cozy cottage steps away from a beautiful beach! Everything you need for a beach weekend is there (beach towels, chairs, toys, an ice chest, and even 2 cute beach bikes!"
The price is AED 735
AED 1,623 total
includes taxes & fees
2 Jun - 3 Jun
Beach house
Tastefully remodeled pool home 7 minutes from the Siesta Key Beach
10.0 out of 10, Exceptional, (29)
"House was very clean. The mattress in the master bedroom was the most comfortable we have laid on. Normal the mattress is a bad experience but not here. Property was conveniently located near all the area attractions we had planned."
Tastefully remodeled pool home 7 minutes from the Siesta Key Beach
City Escape near Sarasota Downtown
9.8 out of 10, Exceptional, (18)
"The pool was nice way to refresh after a busy day."
City Escape near Sarasota Downtown
Modern Private House with Pool near Siesta Key Beach and a Downtown.
10.0 out of 10, Exceptional, (11)
"Top-notch clean. Lovely decorations. Very appealing for family stay!"
Modern Private House with Pool near Siesta Key Beach and a Downtown.
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
9.8 out of 10, Exceptional, (118)
"Excellent vacation property right at the beautiful Siesta beach. We've rented both units, so we had the whole house and pool area all to ourselves. All details in the house are well though through, house is extremely clean and quiet. Large bedroms wth comfortable beds and plenty of common space in the front unit, smaller space in the back unit. Variety of food delivery options from restaurants in the area. The beach is short stroll away, my 82 yrs old mom was easily making the walk without her...
The price is AED 5,605
AED 10,910 total
includes taxes & fees
16 Jun - 17 Jun
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
Don't see what you're looking for?
See all available properties in Osprey
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.

Other property types in Osprey

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4368)
"Staff was friendly. Room was great. Very comfortable at a great price. "
The price is AED 503
AED 651 total
includes taxes & fees
3 Jun - 4 Jun
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2004)
"Good location, room are very good and specious, nice appliances. "
The price is AED 469
AED 517 total
includes taxes & fees
2 Jun - 3 Jun
Hibiscus Suites - Gateway to Siesta Key
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (164)
"The units are very spacious, clean and tastefully decorated. The pool is underwhelming as is the hot tub. Access to the beach was as advertised but losing the lounge chairs and umbrellas by 5:00 p.m.,hours before sunset is not ideal, especially for those with mobility issues who want to remain for the sunset, a highlight of the day. My children looked forward to paddle boarding and kayaking (as advertised) and inquired several times during our multiple day stay but were told none were available....
The price is AED 2,231
AED 2,620 total
includes taxes & fees
19 Jun - 20 Jun
The Residences at Siesta Key Beach by Hyatt Vacation Club
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.

Recent reviews of Osprey hotels
Expedia verified reviews