Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, (200)
"Our villa was perfect. We loved the tropical look of the property and how well it was maintained. The location was wonderful, close to the shops, the restaurants, and the beach. The beach was merely 3 blocks away. The property also provided us with bikes, which we used to get around everywhere (the beach, historic downtown area, and even Venice Pier which was a 10 min bike ride). We loved how everything was so close and so much fun to get around on bikes! The beach umbrellas, chairs, water toys,...
Tropical Villas of Venice Beach
Siesta Key Island Rentals
3.0 star property
10.0 out of 10, Exceptional, (15)
"15 minute or less walk to everything you need. "
Siesta Key Island Rentals
Bay House Retreat managed by Beach Retreats
9.8 out of 10, Exceptional, (43)
"Went to Sarasota for Graduation. Perfect home for 3 generations of family to stay. Beautiful property on a baby peninsula into the bay, island right across the way where birds came to roost for the night. Lovely to just sit and watch the bay, but also awesome pool and really enjoyed adding pontoon boat rental. Able to cook most meals at home. Great location for accessing Sarasota and Bradenton schools/restaurants/beaches but also didn’t have much desire to leave the house."
Bay House Retreat managed by Beach Retreats
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Cozy beach getaway! Close to Siesta Key Beach! Pet Friendly!
8.8 out of 10, Excellent, (21)
"Property was very nice, perfect for our trip. Had a nice lay out well decorated confortable. Very close to the beaches and stores. The only things were that the laundry room and kitchen had a strong musky smell and the hot tub was dirty with residue."
The price is AU$482
includes taxes & fees
23 June - 24 June
Cozy beach getaway! Close to Siesta Key Beach! Pet Friendly!
Beautiful Family-sized Home in Sunny Sarasota, Florida with large backyard!
10.0 out of 10, Exceptional, (1)
"House is in a great location. Was concerned about it being too close to the roadway but we honestly didn't hear any traffic. Prop manager was great and easy to work with. Had a small concern before checking in and the issue was resolved by the time we reached the house. Great location in proximity to Siesta beach. Supplied beach items was great too. Looking forward to being able to stay there again in the future."
Beautiful Family-sized Home in Sunny Sarasota, Florida with large backyard!
Chic Downtown Gem - The Cocoanut Hut, newly constructed
9.8 out of 10, Exceptional, (13)
"The property was exactly as advertised! Clean beautiful home in a central location. The host was very easy to communicate with and helpful!"
Chic Downtown Gem - The Cocoanut Hut, newly constructed
Retreat Half-Mile to Beach/Siesta Key Village
8.8 out of 10, Excellent, (28)
"The property was nice, there were three beds and n air mattress with a built in pump. There was also a large backyard and a wagon with all kinds of beach things. There is no garbage disposal in the sink and the laundry unit is not in the main house but besides those things it was a great place to rent. Walking to the beach is totally doable and you can get free rides from the frog bus (whose name I don't remember) just have to tip a couple bucks. "
Retreat Half-Mile to Beach/Siesta Key Village
Perfect Location. Private Heated Pool/Spa w/ Waterslide
9.2 out of 10, Wonderful, (47)
"Very nice property, the grandchildren loved the pool! Beds were comfortable and everything was well maintained."
Perfect Location. Private Heated Pool/Spa w/ Waterslide
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
9.8 out of 10, Exceptional, (70)
"The property was clean and a great location!"
The price is AU$790
includes taxes & fees
23 June - 24 June
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Waterfront hideaway on Siesta Key in Sarasota, Florida
10.0 out of 10, Exceptional, (208)
"So Peaceful, I enjoyed watching the mullet jump."
Waterfront hideaway on Siesta Key in Sarasota, Florida
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota Florida
8.4 out of 10, Very good, (115)
"Comfortable and clean. Great view of marina."
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota Florida
HAPPY FUN BLUE HOUSE kids, pets friendly, 3 miles away from the beach🏖️.
9.8 out of 10, Exceptional, (33)
"We stayed for 4 days and had a great time! Our dog loved the fenced in backyard and the house was perfect for our family. The inside of the home is nicely updated and had enough supplies for everything we needed. We would definitely stay here again!"
The price is AU$658
includes taxes & fees
22 July - 23 July
HAPPY FUN BLUE HOUSE kids, pets friendly, 3 miles away from the beach🏖️.
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very good, (27)
"This place was great I highly recommend it . The bed was hard and not comfortable and the couch was not very comfortable but the location and cleanliness of this place was great . We would definitely come back and stay . "
The price is AU$610
includes taxes & fees
26 June - 27 June
Siesta Heron Suites & Villas
The Turtle House-Miles and Miles of Private Beach-Sunset Views
9.4 out of 10, Exceptional, (13)
"What a great experience and beautiful location! We are from Miami and we never get tired of great finds like this one. Andrew was really nice and attentive, and extremely accommodating. We were right on the beach! Exclusivity is a guarantee. Will definitely be returning again!"
The price is AU$1,475
includes taxes & fees
9 July - 10 July
The Turtle House-Miles and Miles of Private Beach-Sunset Views
Pool, Hot tub, Close to Beaches, Shopping, More!
9.6 out of 10, Exceptional, (14)
"Great place very clean and hreat neighborhood. Very private and relaxing. Will definitely stay there again!!!"
Pool, Hot tub, Close to Beaches, Shopping, More!
Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village
9.8 out of 10, Exceptional, (17)
"The place was very nice. The bathroom situation was weird. It was a bit expensive and that stressed my mom out. The kitchen had everything you could possibly need. I wish I would have gotten a place with a pool. We loved the large living and dining area, the beds and pillows were not very comfortable"
Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village
Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach
10.0 out of 10, Exceptional, (116)
"House was as described. Clean and well maintained You can tell that its loved 😊 I would definitely book again"
Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach
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 AU$672
includes taxes & fees
23 June - 24 June
Beach house
Beautiful, Spacious Heated Pool Home - Close to Siesta Key Beach!
10.0 out of 10, Exceptional, (5)
"Very nice home w an amazing private pool. Really good location that’s close to shops and restaurants. The beach is close too. I’ll be happy to return asap"
Beautiful, Spacious Heated Pool Home - Close to Siesta Key Beach!
Perfect home away, modern amenities, ~ Heated Pool ~ Close to S. Venice Beach
10.0 out of 10, Exceptional, (170)
"We had a very nice and relaxing stay in Venice , Fl. We would come back to this property again."
Perfect home away, modern amenities, ~ Heated Pool ~ Close to S. Venice Beach
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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, (4421)
"The property was nice. I thought I reserved a king suite Turns out it was a queen studio. Which was way too small. The air conditioning in was off. Took a couple of hours to cool. Overall it was ok"
The price is AU$281
includes taxes & fees
23 June - 24 June
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2017)
"I felt safe during my stay. The place is close to the main attractions of the town/village. Front desk was friendly and helpful."
The price is AU$194
includes taxes & fees
26 June - 27 June
Hibiscus Suites - Gateway to Siesta Key
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, (1041)
"Would recommend this place to others. Good price for so close to the Siesta Key Beach. "
The price is AU$355
includes taxes & fees
27 June - 28 June
Captiva Beach Resort
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.

Osprey Holiday Homes information

Number of reviews
1,150
Accommodation
3129 Holiday Homes
Lowest Price
AU$482
Highest Price
AU$1,475

Recent Reviews in Osprey
Expedia verified reviews