A marina with docked boats, a wooden bridge, and a building with a red roof.

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Osprey villas

A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

1. AUTUMN SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi

AUTUMN SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
Sarasota
9.4 out of 10, Exceptional, (51 reviews)
"The condo is beautifully furnished and equipped with everything we needed. It was very comfortable and we would definitely stay there again."
United States
Sharon M.
The price is HK$988
HK$3,755 total
includes taxes & fees
9 Sept - 10 Sept
AUTUMN SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

2. BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
Sarasota
9.6 out of 10, Exceptional, (53 reviews)
"Beautiful apartment located near the beach and state parks"
United States
Eliot f.
The price is HK$988
HK$3,755 total
includes taxes & fees
9 Sept - 10 Sept
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
A sunlit balcony with a round glass table and wicker chairs, overlooking a well-maintained lawn and a house in the background.

3. 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, (25 reviews)
"Excellent stay. Very clean and facilities were great "
United Kingdom
Jennie A.
The price is HK$1,185
HK$3,154 total
includes taxes & fees
8 Sept - 9 Sept
Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
A patio with a round table and chairs, a blue umbrella, and a view of a building with a balcony.

4. 1 Bedroom/1 Bath Villa (Ground Level) - Unit 11

1 Bedroom/1 Bath Villa (Ground Level) - Unit 11
Casey Key
The price is HK$1,764
HK$2,549 total
includes taxes & fees
9 Sept - 10 Sept
1 Bedroom/1 Bath Villa (Ground Level) - Unit 11
A bicycle parked outside a building with a 'Hello' mat at the entrance.

5. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.4 out of 10, Exceptional, (39 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
The price is HK$590
HK$1,954 total
includes taxes & fees
13 Sept - 14 Sept
[Beach Elements] pool view withprivate beach access
A residential house with a fenced front yard, a parked car, and a palm tree.

6. Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk

Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
South Village
9.6 out of 10, Exceptional, (63 reviews)
"Great location! Close to the beach, pool and restaurants. We had a car but never needed it. We had a great stay."
United States
Joellen M.
The price is HK$776
HK$2,376 total
includes taxes & fees
8 Sept - 9 Sept
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
A modern kitchen with white cabinets, a dining area with a round table and chairs, and large windows offering a view of greenery.

7. 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.
The price is HK$1,764
HK$2,549 total
includes taxes & fees
12 Sept - 13 Sept
ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
A swimming pool with lounge chairs and a hammock, surrounded by a metal roof and lush greenery.

8. Sea Glass Serenity, 3+2, Nokomis Beach, Heated Pool

Sea Glass Serenity, 3+2, Nokomis Beach, Heated Pool
Nokomis
10.0 out of 10, Exceptional, (3 reviews)
"Everything was excellent! I would rent this again if the opportunity were there!"
United States
Sue H.
The price is HK$1,725
HK$5,891 total
includes taxes & fees
8 Sept - 9 Sept
Sea Glass Serenity, 3+2, Nokomis Beach, Heated Pool
A house with a vibrant fish mural on the side, a paved pathway, and a small garden area with palm trees.

9. 2 Bedroom/2 Bath Villa (Ground Level) - Unit 7

2 Bedroom/2 Bath Villa (Ground Level) - Unit 7
Casey Key
10.0 out of 10, Exceptional, (2 reviews)
"Clean and updated cottage across the street from beach and walking distance to two restaurants. Responsive management and easy to work with. Quiet sleeping . Nice stay"
United States
Joanne K.
The price is HK$2,117
HK$3,477 total
includes taxes & fees
8 Sept - 9 Sept
2 Bedroom/2 Bath Villa (Ground Level) - Unit 7
A building with a mural of birds and flowers on the side.

10. 2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A

2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A
Casey Key
10.0 out of 10, Exceptional, (1 review)
"Perfect getaway"
United States
Joseph K.
The price is HK$2,117
HK$3,477 total
includes taxes & fees
8 Sept - 9 Sept
2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A
A modern living room with a leather sofa, a glass coffee table, and a dining area with a white table and chairs.

11. 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 HK$2,117
HK$3,493 total
includes taxes & fees
14 Sept - 15 Sept
2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C

12. 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 HK$3,003
HK$4,833 total
includes taxes & fees
14 Sept - 15 Sept
3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B
A covered patio with a table and chairs, a wooden fence, and a view of a backyard with a barbecue grill.

13. 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, (47 reviews)
"Yes everything was great had a wonderful time "
United States
Melinda M.
The price is HK$1,321
HK$2,845 total
includes taxes & fees
13 Sept - 14 Sept
Turtle Cay at The Beach Shack! Come On Down!
A modern single-story house with a paved driveway, a basketball hoop, and a well-maintained lawn.

14. HeatedPool • HotTub • OutdoorKitchen/Theater/Games

HeatedPool • HotTub • OutdoorKitchen/Theater/Games
South Bradenton
The price is HK$685
HK$4,303 total
includes taxes & fees
9 Sept - 10 Sept
HeatedPool • HotTub • OutdoorKitchen/Theater/Games
A single-story house with a white exterior, a dark roof, and a front door.

15. Lakefront 2BR Bradenton Rental Near IMG & Beaches

Lakefront 2BR Bradenton Rental Near IMG & Beaches
South Bradenton
8.8 out of 10, Excellent, (3 reviews)
"Very clean. No tissues or napkins🤔. Recommend pump hand soap instead of little bars. Also, 2 outdoor chaises were ripped and 1 out of 2 outdoor chairs was broken and unable to use the.."
United States
Laura
The price is HK$638
HK$1,709 total
includes taxes & fees
22 Sept - 23 Sept
Lakefront 2BR Bradenton Rental Near IMG & Beaches
A turquoise building with a tiled driveway and a row of bicycles parked in front.

16. 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, (44 reviews)
"Location was great, property condition is excellent!"
United States
Mabel
The price is HK$1,321
HK$2,900 total
includes taxes & fees
10 Sept - 11 Sept
Flamingo's Nest at the Beach Shack. Just one block from the beach!

17. Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches

Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
Englewood South
10.0 out of 10, Exceptional, (4 reviews)
"This was a wonderful vacation! The house was perfect! Very clean and decorated beautifully! We had everything that we needed! Great location too! We would recommend this house to anyone coming to Englewood, it was wonderful! We will be coming back! Thank you for sharing your beautiful house with us!!"
United States
Lisa M.
The price is HK$949
HK$3,161 total
includes taxes & fees
4 Oct - 5 Oct
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
A residential property with a driveway leading to a house, surrounded by well-maintained lawns and large trees with hanging moss.

18. Heated Pool • Sleeps 22 • Pickle/Bball • Theater

Heated Pool • Sleeps 22 • Pickle/Bball • Theater
Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"Great spot to have for a team playing in IMG events."
United States
Adam D.
The price is HK$1,948
HK$6,894 total
includes taxes & fees
8 Sept - 9 Sept
Heated Pool • Sleeps 22 • Pickle/Bball • Theater
A two-story building with a sign reading 'Beach Shack.'

19. 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, (44 reviews)
"Wonderful place and a great location "
United States
Matthew C.
The price is HK$1,321
HK$2,845 total
includes taxes & fees
10 Sept - 11 Sept
Seashell Shanty at The Beach Shack! Come On Down!
A residential house at dusk with a well-lit pathway, a palm tree, and a garden with various plants.

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

Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
North Port
10.0 out of 10, Exceptional, (11 reviews)
"This house is one of the nicest homes we've ever stayed in. Everything in the house is so beautiful, and it's so well stocked with everything we could possibly need. It was the perfect location for enjoying Spring Training games, and my daughter loved the heated pool."
United States
Tracy B.
The price is HK$2,039
HK$5,220 total
includes taxes & fees
8 Sept - 9 Sept
Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
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

Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"Really nice hotel clean breakfast really good"
Daniel 2-night trip
Posted 3 hours ago
Hyatt Place Sarasota/Bradenton Airport

Find out more about Osprey

Osprey Villas information

Number of reviews
328
Accommodation
482 Villas
Lowest Price
HK$1,709
Highest Price
HK$6,894

Frequently asked questions

How much do villas in Osprey cost?
Villas in Osprey cost between HK$1,709 and HK$6,894 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 9.9. 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 482 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 HK$1,709 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.

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