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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Osprey villas

Terrace/patio

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
9.6 out of 10, Exceptional, (49 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$811
HK$3,513 total
includes taxes & fees
9 Jun - 10 Jun
AUTUMN SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
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, (24 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 HK$1,142
HK$3,096 total
includes taxes & fees
10 Jun - 11 Jun
Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
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 HK$1,237
HK$2,802 total
includes taxes & fees
9 Jun - 10 Jun
Seashell Shanty at The Beach Shack! Come On Down!
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, (43 reviews)
"The beach shack was loaded with everything needed to have a very comfortable stay. The location is fantastic with the beach and several restaurants all within walking distance. I will definitely be back!"
United States
Anne Marie B.
The price is HK$1,237
HK$2,802 total
includes taxes & fees
9 Jun - 10 Jun
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, (45 reviews)
"Yes everything was great had a wonderful time "
United States
Melinda M.
The price is HK$1,237
HK$2,802 total
includes taxes & fees
13 Jun - 14 Jun
Turtle Cay at The Beach Shack! Come On Down!
Outdoor pool, a heated pool

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$1,142
HK$3,335 total
includes taxes & fees
28 Jun - 29 Jun
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
Exterior

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$1,120
HK$2,292 total
includes taxes & fees
14 Jun - 15 Jun
Lakefront 2BR Bradenton Rental Near IMG & Beaches
Exterior

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (33 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$791
HK$2,273 total
includes taxes & fees
9 Jun - 10 Jun
[Beach Elements] pool view withprivate beach access
Terrace/patio

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, (52 reviews)
"Beautiful apartment located near the beach and state parks"
United States
Eliot f.
The price is HK$940
HK$3,651 total
includes taxes & fees
1 Jul - 2 Jul
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
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, (38 reviews)
"Great place with snacks!"
United States
Nancy N.
The price is HK$1,653
HK$3,638 total
includes taxes & fees
9 Jun - 10 Jun
Pineapple Express at the Beach Shack Just one block from the beach!
Property grounds

For family fun or a romantic escape close to sarasota and the area"s beaches

For family fun or a romantic escape close to sarasota and the area"s beaches
Bayshore Gardens
9.6 out of 10, Exceptional, (5 reviews)
"It seemed to be recently remodeled in excellent condition. Good safe location. Lots of room for a couple but had an extra bedroom so it would work great for a family. The outdoor area was huge with a great gas grill area. Lots of extra little touches like coffee tea chocolate andchampagne."
United States
Steve R.
The price is HK$1,175
HK$2,227 total
includes taxes & fees
21 Jun - 22 Jun
For family fun or a romantic escape close to sarasota and the area"s beaches
Exterior detail

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)
"The home is absolutely beautiful- the interior design is gorgeous, welcoming and makes you feel like you are staying in a very special place. The pool was warm and view of canal in the backyard is stunning. The home is very well stocked with all the basics which was so helpful!"
United States
Anonymous traveller
The price is HK$2,037
HK$5,521 total
includes taxes & fees
10 Jun - 11 Jun
Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
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, (27 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 HK$1,653
HK$3,638 total
includes taxes & fees
14 Jun - 15 Jun
Seaglass Inn at the Beach Shack Just one block from the beach!
Exterior

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, (59 reviews)
"Great place! Love having a private place to stay with all we need including great beach toys, chairs and umbrellas!"
United States
Tanya V.
The price is HK$776
HK$2,382 total
includes taxes & fees
25 Jun - 26 Jun
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
Exterior

Heated Pool and Spa • Outdoor Kitchen/Theater/Games

Heated Pool and Spa • Outdoor Kitchen/Theater/Games
South Bradenton
2.0 out of 10, (1 review)
"Where do I start. We arrived in the house to find there are not seven bedrooms, but six. The pool was not clean it had leaves and other items at the bottom as well as the hot tub had a used filter laying in it along with other debris and was cold. The hot tub took 24 hours to heat up. The house itself is very weird in the set up and the furniture inside. Looks like it was bought at a yard sale. The hot water on one side of the house did not work in one of the showers and one of the...
United States
William R.
The price is HK$1,304
HK$5,080 total
includes taxes & fees
23 Jun - 24 Jun
Heated Pool and Spa • Outdoor Kitchen/Theater/Games
Outdoor dining

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

1 Bedroom/1 Bath Villa (Ground Level) - Unit 11
Casey Key
The price is HK$2,013
HK$2,862 total
includes taxes & fees
17 Jun - 18 Jun
1 Bedroom/1 Bath Villa (Ground Level) - Unit 11
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.
The price is HK$2,013
HK$2,862 total
includes taxes & fees
16 Jun - 17 Jun
ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
Outdoor pool, a heated pool

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$2,546
HK$7,888 total
includes taxes & fees
6 Jul - 7 Jul
Sea Glass Serenity, 3+2, Nokomis Beach, Heated Pool
Exterior

Completely Remodeled- 150 Yards to Beach and Restaurants!

Completely Remodeled- 150 Yards to Beach and Restaurants!
South Village
10.0 out of 10, Exceptional, (41 reviews)
"Great unit—clean, well-equipped with everything we needed, including beach gear. Near a beautiful beach, great restaurants, and trolley. Owner was easy to work with. Looking forward to returning."
United States
Vicky C.
The price is HK$1,939
HK$4,239 total
includes taxes & fees
15 Jun - 16 Jun
Completely Remodeled- 150 Yards to Beach and Restaurants!
Property grounds

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$2,366
HK$3,813 total
includes taxes & fees
19 Jun - 20 Jun
2 Bedroom/2 Bath Villa (Ground Level) - Unit 7
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

10/10 Excellent
"Everything was good"
Eric 2-night trip
Posted less than an hour ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Osprey Villas information

Number of reviews
481
Accommodation
443 Villas
Lowest Price
HK$2,227
Highest Price
HK$7,888

Frequently asked questions

How much do villas in Osprey cost?
Villas in Osprey cost between HK$2,227 and HK$7,888 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 9.4. 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 443 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$2,227 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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