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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

3.0 star property
9.4 out of 10, Exceptional, (427)
"Everything was great. Great people to work with."
Venice Beach Villas

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

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.

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.

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!

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

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."
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

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

9.8 out of 10, Exceptional, (259)
"Great location! Beautiful beach! "
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building

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

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!

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

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! "
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

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

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,

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

10.0 out of 10, Exceptional, (113)
"Great place to stay. Accomodations were very good."
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

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..

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

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from to 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.