Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, 202 reviews
"We loved our stay at Tropical Villas. The property is beautiful. Its small and private and located close to everything. We used the grills, the beach chairs and the pool. It was like a home away from home. "
Tropical Villas of Venice Beach
Siesta Key Island Rentals
Room amenity
Siesta Key Island Rentals
3.0 star property
10.0 out of 10, Exceptional, 15 reviews
"15 minute or less walk to everything you need. "
Siesta Key Island Rentals
Cozy beach getaway! Close to Siesta Key Beach! Pet Friendly!
Fridge, microwave, oven, stovetop
Cozy beach getaway! Close to Siesta Key Beach! Pet Friendly!
9.0 out of 10, Wonderful, 22 reviews
" Very clean nice presentation i would come back a weekend "
The price is AU$483
per night
28 June - 29 June
Cozy beach getaway! Close to Siesta Key Beach! Pet Friendly!
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Beautiful Family-sized Home in Sunny Sarasota, Florida with large backyard!
Sun-loungers, beach towels
Beautiful Family-sized Home in Sunny Sarasota, Florida with large backyard!
10.0 out of 10, Exceptional, 1 review
"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!
Retreat Half-Mile to Beach/Siesta Key Village
Fridge, microwave, stovetop, dishwasher
Retreat Half-Mile to Beach/Siesta Key Village
8.8 out of 10, Excellent, 28 reviews
"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
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Beach nearby, sun-loungers, beach towels
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
9.8 out of 10, Exceptional, 82 reviews
"Great place, great location. Short walk to gulf and St Armand Circle. Nice house, accurate description. Quiet and clean."
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Fridge, microwave, oven, stovetop
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
9.8 out of 10, Exceptional, 70 reviews
"The property was clean and a great location!"
The price is AU$808
per night
2 July - 3 July
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Waterfront hideaway on Siesta Key in Sarasota, Florida
Sport court
Waterfront hideaway on Siesta Key in Sarasota, Florida
10.0 out of 10, Exceptional, 209 reviews
"The house was as advertised and the property was even better and more private than expected. Had all amenities for a shorty or long stay and the host was easy to communicate with. Definitely recommend this property."
Waterfront hideaway on Siesta Key in Sarasota, Florida
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota Florida
Iron/ironing board, free WiFi, bed sheets
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota Florida
8.4 out of 10, Very good, 115 reviews
"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🏖️.
Exterior
HAPPY FUN BLUE HOUSE kids, pets friendly, 3 miles away from the beach🏖️.
9.8 out of 10, Exceptional, 33 reviews
"Great house, questionable neighborhood. But peaceful Loved our stay, great family time- At house and beach!"
The price is AU$657
per night
22 July - 23 July
HAPPY FUN BLUE HOUSE kids, pets friendly, 3 miles away from the beach🏖️.
Perfect home away, modern amenities, ~ Heated Pool ~ Close to S. Venice Beach
Beach nearby
Perfect home away, modern amenities, ~ Heated Pool ~ Close to S. Venice Beach
10.0 out of 10, Exceptional, 170 reviews
"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
Florida Beach Cottage 4BR-2BA
Property grounds
Florida Beach Cottage 4BR-2BA
9.4 out of 10, Exceptional, 3 reviews
"My family really enjoyed this home which has everything needed for comfortable stay and The location is fantastic as it’s just 5 minutes to Nokomis and Casey Key."
Florida Beach Cottage 4BR-2BA
The Turtle House-Miles and Miles of Private Beach-Sunset Views
Outdoor dining
The Turtle House-Miles and Miles of Private Beach-Sunset Views
9.6 out of 10, Exceptional, 14 reviews
"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$1,477
per night
9 July - 10 July
The Turtle House-Miles and Miles of Private Beach-Sunset Views
Pool, Hot tub, Close to Beaches, Shopping, More!
Smart TV, table football, books
Pool, Hot tub, Close to Beaches, Shopping, More!
9.6 out of 10, Exceptional, 15 reviews
"Management was great, house was clean, was a great stay!"
Pool, Hot tub, Close to Beaches, Shopping, More!
Minutes Away from Beach Cabana Breeze
TV, DVD player, books, stereo
Minutes Away from Beach Cabana Breeze
9.0 out of 10, Wonderful, 7 reviews
"Only 15 minutes from some of my favorite beaches as a Floridian :) the property could use a good deep clean but we still enjoyed our 4 day stay"
Minutes Away from Beach Cabana Breeze
Perfect Location. Private Heated Pool/Spa w/ Waterslide
Pool
Perfect Location. Private Heated Pool/Spa w/ Waterslide
9.2 out of 10, Wonderful, 47 reviews
"Very nice property, the grandchildren loved the pool! Beds were comfortable and everything was well maintained."
Perfect Location. Private Heated Pool/Spa w/ Waterslide
Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach
Beach nearby, sun-loungers, beach towels
Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach
10.0 out of 10, Exceptional, 116 reviews
"This was a very comfortable and cozy home. House was very clean and adequately equipped with everything you needed. Host communicated promptly. Would definitely stay there again"
Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach
Beach house
Property grounds
Beach house
10.0 out of 10, Exceptional, 22 reviews
"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
per night
29 June - 30 June
Beach house
Beautiful 5 Bedroom Home Directly on Siesta Key Beach!!
Property grounds
Beautiful 5 Bedroom Home Directly on Siesta Key Beach!!
10.0 out of 10, Exceptional, 2 reviews
"Excellent directly on the Beach clean and walking distance to all the shops 💕"
Beautiful 5 Bedroom Home Directly on Siesta Key Beach!!
Home Steps from Siesta Key Beach and Village with Waterslide! On The Rocks
A heated pool
Home Steps from Siesta Key Beach and Village with Waterslide! On The Rocks
10.0 out of 10, Exceptional, 33 reviews
"We loved our stay at this property in Siesta Key. We couldn’t get our kids out of the pool with the awesome slide long enough to even go to the beach. Very walkable to Siesta Key Village and all of the restaurants and entertainment there and very close to the beach."
Home Steps from Siesta Key Beach and Village with Waterslide! On The Rocks
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
Property amenity
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, 4,425 reviews
"Great place to stay and close to beach entrance. Restaurants close by "
The price is AU$282
per night
3 July - 4 July
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, 2,020 reviews
"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$217
per night
1 July - 2 July
Hibiscus Suites - Gateway to Siesta Key
Captiva Beach Resort
Florida Family Single | Private kitchen
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, 1,042 reviews
"Would recommend this place to others. Good price for so close to the Siesta Key Beach. "
The price is AU$330
per night
1 July - 2 July
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
1,188
Accommodation
3129 Holiday Homes
Lowest Price
AU$483
Highest Price
AU$1,477

Recent Reviews in Osprey
Expedia verified reviews

The Westin Sarasota

The Westin Sarasota

5/5 Excellent
"Only downside was the $45/night parking fee. "
A verified traveller from Ithaca stayed at The Westin Sarasota
Posted 1 day ago
The Westin Sarasota