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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Captiva Beach Resort
Relax in the Captiva chair, surrounded by lush greenery and a stylish sign.

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1122)
"Everything was perfect with our stay. We will be back soon."
Captiva Beach Resort
Venice Beach Villas
Relax in our outdoor patio area, featuring a seating arrangement, barbecue grill, and lush greenery.

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (427)
"Easy walk or bike ride to beach. Property has plenty of bikes to borrow with locks. Overall just super place that I’ll stay again. "
Venice Beach Villas
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Enjoy a tranquil beach experience with a wide, sandy beach and calm ocean views.

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

8.8 out of 10, Excellent, (21)
"Great view and nice place for a short stay. "
The price is HK$1,884
HK$3,646 total
includes taxes & fees
11 Aug - 12 Aug
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Cozy condo in charming Sarasota Siesta key with boat dock
Relax on the spacious deck with a sofa, chairs, fire pit, and grill station, offering a comfortable seating area under a retractable awning.

Cozy condo in charming Sarasota Siesta key with boat dock

10.0 out of 10, Exceptional, (2)
"Amazing getaway! The location by the water was perfect for relaxing by boat. Cozy and well-equipped, we loved every moment. Highly recommend for a peaceful, scenic retreat."
Cozy condo in charming Sarasota Siesta key with boat dock
Take a Peek at a fabulous unit.
Enjoy breathtaking ocean views from your balcony amidst lush palm trees and a serene beachfront setting.

Take a Peek at a fabulous unit.

10.0 out of 10, Exceptional, (122)
"You can not get any closer to the beach than this. The view, the room and our property manager were all amazing. ZERO complaints. Can't wait to go back. "
Take a Peek at a fabulous unit.
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
Enjoy a tranquil seaside escape with a beachfront view of the ocean and lush greenery.

DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.

10.0 out of 10, Exceptional, (90)
"A beautiful view with amazing comfort in the condo! I can’t wait to come back!❤️😎"
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
Enjoy access to the ocean from this beachfront property.

DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!

9.8 out of 10, Exceptional, (58)
"Really nice property. So glad it survived the hurricane. Can’t wait to stay there again. "
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Relax on the balcony overlooking the beach, where a pool and lounge chairs await.

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

9.0 out of 10, Wonderful, (17)
"The property was great for our family, loved having a pool and beach access. Super simple especially with a toddler in tow."
The price is HK$1,806
HK$3,296 total
includes taxes & fees
11 Aug - 12 Aug
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Relax on the wide, open beach with comfortable beach tents and umbrellas.

1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets

9.6 out of 10, Exceptional, (157)
"We could not have been happier with this location and its proximity to the beach and the pools. It was also close to great restaurants by locals who proudly serve great food!! "
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
Guests can enjoy a serene beach experience with clear blue waters and soft sandy shores.

Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building

9.8 out of 10, Exceptional, (259)
"Great location! Beautiful beach! "
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
Prime Beachfront with Views, Views, Views!
Enjoy breathtaking views of the ocean from your balcony overlooking the white sandy beach and lush green lawn.

Prime Beachfront with Views, Views, Views!

9.6 out of 10, Exceptional, (82)
"The condo was clean, nicely decorated, spacious and very comfortable! It was steps from the beach and pool! The beach is absolutely beautiful! The pool was very nice! We would definitely stay here again! The beds are very comfortable and having two full bathrooms was so nice! We had a great week! "
Prime Beachfront with Views, Views, Views!
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Relax by the pool surrounded by palm trees and enjoy a refreshing swim.

Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club

9.8 out of 10, Exceptional, (28)
"Fantastic location!!! Beautiful Beach!! Very clean and updated condo Definitely would stay there again!!! Perfect place to eat, sleep, beach and Repeat!! Loved it!!! "
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Sand in Your Toes . . . Right Out Your Front Door!
Relax in a serene outdoor seating area with a table and benches, shaded by a palm tree and offering a view of the ocean.

Sand in Your Toes . . . Right Out Your Front Door!

9.4 out of 10, Exceptional, (113)
"Clean & comfortable with the beach just steps away!"
Sand in Your Toes . . . Right Out Your Front Door!
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
Enjoy the serene beach experience with gentle waves lapping at the shore.

Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC

6.6 out of 10, (7)
"Great location and beach access- pool is awesome! Unit doesn’t face the ocean, but it’s right there! Very low key- place is very clean. WiFi is spotty and would not be good if you are planning to work while staying- that is an island wide issue I believe- No stove, but has everything else a kitchen needs and a grill- we would come back! "
The price is HK$2,277
HK$3,698 total
includes taxes & fees
11 Aug - 12 Aug
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Cozy living area with sofa, dining table for four, and a large flat-screen TV.

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (93)
"Lovely unit and the perfect location. Short walk to the beach and easy to get to the shopping/eating areas. "
The price is HK$1,236
HK$3,222 total
includes taxes & fees
22 Aug - 23 Aug
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Spacious Penthouse 3bd/3bath, On the Beach, Great Views!
Enjoy a beachfront retreat with ocean views, a lush lawn, and comfortable lounge chairs.

Spacious Penthouse 3bd/3bath, On the Beach, Great Views!

10.0 out of 10, Exceptional, (161)
"Absolutely fantastic!! "
Spacious Penthouse 3bd/3bath, On the Beach, Great Views!
On Siesta Key/Crescent Beach,View, pool, 2 Bed 2 Ba, plus pull out Queen,
Enjoy cooking in this well-equipped kitchen with a microwave, stove, and dishwasher.

On Siesta Key/Crescent Beach,View, pool, 2 Bed 2 Ba, plus pull out Queen,

10.0 out of 10, Exceptional, (175)
"Love the condo. I just wish the ocean view was better"
On Siesta Key/Crescent Beach,View, pool, 2 Bed 2 Ba, plus pull out Queen,
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
Enjoy serene beach views and unwind in a tranquil setting.

Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

10.0 out of 10, Exceptional, (113)
"Great place to stay. Accomodations were very good."
The price is HK$785
HK$2,409 total
includes taxes & fees
23 Aug - 24 Aug
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.
Relax by the resort's central pool surrounded by lush greenery and palm trees.

4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.

10.0 out of 10, Exceptional, (141)
"We love Siesta Dunes! The property is clean and well-maintained. Our unit was beautiful and true to the pictures. The views were outstanding. The owner, Tom, was responsive and helpful with suggestions! We had no issues at all."
4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.
Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..
Relax by the ocean with a gazebo and comfortable seating for two.

Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..

9.8 out of 10, Exceptional, (7)
"The rental was spacious and very clean!!I would definitely stay here again. Place looked exactly like the pictures!! "
Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..
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
"Buena relación entre precio y servicio"
Laura 1-night trip
Posted 1 day ago
Spark by Hilton Sarasota Siesta Key Gateway

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from HK$785 to HK$2,277 per night. These stays provide loads of space for your whole crew at a price that's friendly on the pocket. 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 condos in Osprey?
Choose from multiple condos in Osprey with a total average guest review rating of 9.4. Venice Beach Villas comes highly recommended if you're travelling with the whole crew or just want to stretch out. This 3-star condo also features therapeutic mineral springs and a barbecue grill. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is another guest fave. It has a 3-star rating and amenities such as a deck and a lanai.
How many condos are there in Osprey?
Work out your holiday dates and then pick from 3731 condos in Osprey. For an official business trip, a couples' getaway or anything in between, Expedia will help you find the perfect place in a few quick clicks.