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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Osprey villas

Exterior

Lakefront 2BR Bradenton Rental Near IMG & Beaches

Lakefront 2BR Bradenton Rental Near IMG & Beaches
South Bradenton
8.0 out of 10, Very good, (2 reviews)
"I just want to say the place is nice, but it needs more cleaning. There was a lot of pet hair, and the floor was dirty. These are small things, but if they paid a little more attention to those details, it would be absolutely fantastic, a perfect 100. If you asked me if I would recommend it, my answer would be yes. As I said before, the place is very nice, comfortable, and cozy, and the neighborhood is very quiet. Would I go back? Of course I would, just please, more cleaning!"
United States
Maria I
The price is €225
includes taxes & fees
14 Apr - 15 Apr
Lakefront 2BR Bradenton Rental Near IMG & Beaches
Outdoor dining

Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA

Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
Sarasota
9.6 out of 10, Exceptional, (18 reviews)
"Such a relaxing villa just 15 minutes from Siesta Key! We had such a wonderful time relaxing, hanging at the pool, and visiting the local shops. If you’re looking for a place to stay, choose this condo, you will not regret 😊"
United States
Sommer
The price is €403
includes taxes & fees
2 Apr - 3 Apr
Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
Exterior

Flamingo's Nest at the Beach Shack. Just one block from the beach!

Flamingo's Nest at the Beach Shack. Just one block from the beach!
Manasota Key
10.0 out of 10, Exceptional, (41 reviews)
"Location was great, property condition is excellent!"
United States
Mabel
Flamingo's Nest at the Beach Shack. Just one block from the beach!
Exterior

Turtle Cay at The Beach Shack! Come On Down!

Turtle Cay at The Beach Shack! Come On Down!
Manasota Key
10.0 out of 10, Exceptional, (44 reviews)
"This was such a cute place to stay rhat is conveniently located via walking diatance to the beach and local restaurants. "
United States
Renay S.
The price is €429
includes taxes & fees
2 Apr - 3 Apr
Turtle Cay at The Beach Shack! Come On Down!
Exterior

Seaglass Inn at the Beach Shack Just one block from the beach!

Seaglass Inn at the Beach Shack Just one block from the beach!
Manasota Key
10.0 out of 10, Exceptional, (24 reviews)
"The host was more than accommodating! The place was so clean and had all the amenities you could want at the beach. "
United States
Katy D.
The price is €611
includes taxes & fees
31 Mar - 1 Apr
Seaglass Inn at the Beach Shack Just one block from the beach!
Terrace/patio

Seashell Shanty at The Beach Shack! Come On Down!

Seashell Shanty at The Beach Shack! Come On Down!
Manasota Key
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful place and a great location "
United States
Matthew C.
The price is €429
includes taxes & fees
2 Apr - 3 Apr
Seashell Shanty at The Beach Shack! Come On Down!
Flat-screen TV, books

ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8

ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
Casey Key
10.0 out of 10, Exceptional, (4 reviews)
"Had a very relaxing time. Nice short walk to the beach"
United States
Mitch K.
ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
Exterior detail

Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool

Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
North Port
9.8 out of 10, Exceptional, (9 reviews)
"Very relaxing..very spacious..decor was outstanding..very clean .and inviting..love it"
United States
MajDeidre F.
The price is €696
includes taxes & fees
29 Mar - 30 Mar
Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
Exterior

Pineapple Express at the Beach Shack Just one block from the beach!

Pineapple Express at the Beach Shack Just one block from the beach!
Manasota Key
10.0 out of 10, Exceptional, (37 reviews)
"Great place with snacks!"
United States
Nancy N.
Pineapple Express at the Beach Shack Just one block from the beach!
Exterior

Quiet Downtown Sarasota Villa. 2 bed 2 bath. 644

Quiet Downtown Sarasota Villa. 2 bed 2 bath. 644
Central Sarasota
8.4 out of 10, Very good, (11 reviews)
"Enjoyed our stay."
United States
Greg M.
The price is €373
includes taxes & fees
18 Mar - 19 Mar
Quiet Downtown Sarasota Villa. 2 bed 2 bath. 644
Exterior

4 Min to Beach • Spacious 3BR Home • 4 Beds • Private Gym • Large Backyard

4 Min to Beach • Spacious 3BR Home • 4 Beds • Private Gym • Large Backyard
Englewood South
4 Min to Beach • Spacious 3BR Home • 4 Beds • Private Gym • Large Backyard
Exterior

Canal Lower-Gorgeous 3 bed 3 bath near SK Village

Canal Lower-Gorgeous 3 bed 3 bath near SK Village
Siesta Key Village
9.6 out of 10, Exceptional, (38 reviews)
"Phenomenal experience and the perfect house! Location, communication, beach access, pool and being that close to the village was great — perfect place to relax and enjoy Siesta!"
United States
Dylan F.
The price is €1,210
includes taxes & fees
31 Mar - 1 Apr
Canal Lower-Gorgeous 3 bed 3 bath near SK Village
TV, books

2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C

2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C
Casey Key
The price is €632
includes taxes & fees
24 Mar - 25 Mar
2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C
Outdoor dining

3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B

3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B
Casey Key
10.0 out of 10, Exceptional, (1 review)
"The escape at Casey key was a great place to stay , was clean rooms were nice and updated and look forward to next Memorial Day weekend"
United States
Roger B.
The price is €775
includes taxes & fees
30 Mar - 31 Mar
3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

8/10 Good
"The room and property were clean and comfy. The staff was great. My only complaint is that there is no fan in the bathroom to disperse the shower steam and there is only one outlet near the sink for blow drying hair and using electric razors, straighteners etc. Other than that the location is great etc. "
Nancy 1-night trip
Posted 1 hour ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Osprey Villas information

Number of reviews
272
Accommodation
385 Villas
Lowest Price
€225
Highest Price
€1,210

Frequently asked questions

How much do villas in Osprey cost?
Villas in Osprey cost between €225 and €1,210 per night. These getaways provide the privacy to enjoy your own space at a price that won't stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Osprey?
Osprey has multiple villas with a total average guest review rating of 9.6. Island House Beach Resort V39 is a popular choice with Expedia guests. Visitors staying at this 3-star retreat will enjoy access to a swimming pool and a barbecue grill. Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is another sought-after stay. This 2.5-star villa offers a barbecue grill and a swimming pool, among other conveniences.
How many villas are there in Osprey?
Take your pick of 385 villas in Osprey. No matter if you're holidaying with the family or getting away with some friends, Expedia will help you find the best space for your whole crew.
What are the best cheap villas in Osprey?
Villas start at €225 per night, so your Osprey adventure doesn't have to stretch your budget! Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is a pocket-friendly pick that comes with plenty of amenities, including a barbecue grill and a swimming pool. Island House Beach Resort V21 is another cheap stay in this sought-after destination. Amenities here include a barbecue grill and a swimming pool. If you're exploring Osprey on a budget, there are loads of popular and free attractions to add to your to-do list. Siesta Key Beach and Venice Beach are visitor favourites. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly villas in Osprey?
Many visitors needing a family-friendly villa in Osprey go for Island House Beach Resort V39. With a 3-star rating and useful amenities like a barbecue grill and clothes washing facilities, you're sure to feel at home here. Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is a 2.5-star stay that's also a hit with travelling families. Clothes washing facilities and WiFi help make it a comfy base for your Osprey getaway. Once you've checked in and unpacked your suitcase, there's no shortage of family-friendly attractions to see around Osprey. Siesta Key Beach and Venice Beach guarantee a good time for young and old.
Why book your villa in Osprey with Expedia?
Expedia makes it a cinch to find your dream villa in Osprey. Getting away with the family? Make the most of our filters to search for stays with amenities like WiFi and a pool. If you need to stick to a budget, choose how much you're willing to spend and the star rating of the property. We'll help you find a perfect place that matches your style and taste.
How can I find cheap villas in Osprey?
The quickest way to zero in on cheap villas in Osprey is with Expedia's handy filter tool. Tailor your search results by amenities, budget and star rating to nab unbeatable prices in just a couple of clicks.
What is there to do near my villa in Osprey?
After you've unpacked your suitcases, set out and explore the fun things Osprey has for you to experience. Oscar Scherer State Park is a popular attraction to add to your to-do list.