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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Condo Rentals in Osprey

Property grounds
Chadwick Cove Resort & Marina
Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
The price is AU$829
includes taxes & fees
26 Oct - 27 Oct
Chadwick Cove Resort & Marina
Sun-loungers, beach towels
Cozy beach house! Just steps away from the world-class Manasota beach
Cozy beach house! Just steps away from the world-class Manasota beach
3.5 star property
9.8 out of 10, Exceptional, (6)
"Nice place to stay, close to the beach, hunting for fossilized shark teeth was fun."
United States
Vance E.
The price is AU$659
includes taxes & fees
23 Oct - 24 Oct
Cozy beach house! Just steps away from the world-class Manasota beach
Beach nearby
New! Renovated Coastal 2/2, 6 mins to IMG
New! Renovated Coastal 2/2, 6 mins to IMG
9.8 out of 10, Exceptional, (17)
"Accommodating for family group, quick drive to the beach."
United States
Ginger B.
The price is AU$575
includes taxes & fees
23 Oct - 24 Oct
New! Renovated Coastal 2/2, 6 mins to IMG
Front of property – evening/night
Captiva Beach Resort
Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1144)
"Great place close to the beach"
United States
Yuditza
Captiva Beach Resort
Exterior
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
9.8 out of 10, Exceptional, (59)
"It was clean, comfy and ideal locarion. Close to beaches AMI and the pool was great. "
United States
Marge G.
The price is AU$632
includes taxes & fees
3 Nov - 4 Nov
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Beach nearby
Modern Coastal 2/2 condo w/pool 6 mins to IMG
Modern Coastal 2/2 condo w/pool 6 mins to IMG
10.0 out of 10, Exceptional, (25)
"Great place to stay !"
Canada
Teddy N.
The price is AU$575
includes taxes & fees
23 Oct - 24 Oct
Modern Coastal 2/2 condo w/pool 6 mins to IMG
Beach
Lavish Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants
Lavish Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants
10.0 out of 10, Exceptional, (114)
"Great place to stay. Accomodations were very good."
United States
Ed H.
The price is AU$471
includes taxes & fees
27 Oct - 28 Oct
Lavish Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants
Exterior
Beach Castle Resort #22 by RVA
Beach Castle Resort #22 by RVA
9.6 out of 10, Exceptional, (45)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The place is really cute and I loved the location. The price was affordable and the resort had a lot of amenities. The beds could be a little softer (I'm not used to firm beds) but it was sleepable. I'd definitely stay here again!"
United States
Eyleah M.
The price is AU$543
includes taxes & fees
23 Oct - 24 Oct
Beach Castle Resort #22 by RVA
Interior
Riverside Oasis 1Bed/1Bath
Riverside Oasis 1Bed/1Bath
9.4 out of 10, Exceptional, (37)
"Perfect little place for a couple days. Clean and conveniently located just a short drive away from everything you need. Host was responsive and accommodating. We would definitely stay here again. "
United States
Adrianne J.
The price is AU$182
includes taxes & fees
26 Oct - 27 Oct
Riverside Oasis 1Bed/1Bath
Sun-loungers, beach towels
Beautifully furnished condo
Beautifully furnished condo
9.8 out of 10, Exceptional, (141)
"The condo was perfect for our needs. It was a few minutes away from IMG, close to attractions, and clean. It had beach gear and towels too! "
United States
Stephanie K.
The price is AU$329
includes taxes & fees
23 Oct - 24 Oct
Beautifully furnished condo
Beach
Beautiful 2BR Condo! 2 Pools~Free WiFi. By IMG Academy~Beaches~AMI~Restaurants.
Beautiful 2BR Condo! 2 Pools~Free WiFi. By IMG Academy~Beaches~AMI~Restaurants.
9.8 out of 10, Exceptional, (144)
"Great location, clean, everything we needed for a low key beach vacation!"
United States
Stephanie H.
The price is AU$464
includes taxes & fees
26 Oct - 27 Oct
Beautiful 2BR Condo! 2 Pools~Free WiFi. By IMG Academy~Beaches~AMI~Restaurants.
Dining
Large Studio on Gulf! Cabana Beach Club #5B Longboat Key-Steps to Sand by RVA
Large Studio on Gulf! Cabana Beach Club #5B Longboat Key-Steps to Sand by RVA
8.2 out of 10, Very good, (72)
"Wonderful spot. Highly recommend. "
United States
Regina T.
The price is AU$430
includes taxes & fees
23 Oct - 24 Oct
Large Studio on Gulf! Cabana Beach Club #5B Longboat Key-Steps to Sand by RVA
Beach nearby, beach umbrellas
The Beach Club at Siesta Key #106A Resort by RVA
The Beach Club at Siesta Key #106A Resort by RVA
9.0 out of 10, Wonderful, (67)
"Our family had a blast - great beach and pools."
United States
Nicholas M.
The price is AU$602
includes taxes & fees
23 Oct - 24 Oct
The Beach Club at Siesta Key #106A Resort by RVA
1 bedroom, desk, iron/ironing board, WiFi
The Sapphire Suite 1Bed/1Bath
The Sapphire Suite 1Bed/1Bath
9.8 out of 10, Exceptional, (84)
"We loved our stay here, it was a perfect location with lots to do within even walking distance! "
United States
Austin S.
The price is AU$225
includes taxes & fees
23 Oct - 24 Oct
The Sapphire Suite 1Bed/1Bath
A heated pool
Sun, Sand & Silver Sands – Gulfside Resort Escape Unit #237 by RVA
Sun, Sand & Silver Sands – Gulfside Resort Escape Unit #237 by RVA
8.8 out of 10, Excellent, (42)
"Enjoyed our stay"
United States
Susan C.
The price is AU$448
includes taxes & fees
23 Oct - 24 Oct
Sun, Sand & Silver Sands – Gulfside Resort Escape Unit #237 by RVA
Dining
Gulfside 2BR Condo–Silver Sands #257S
Gulfside 2BR Condo–Silver Sands #257S
8.6 out of 10, Excellent, (35)
"Very pleasant."
United States
Bridgit M.
The price is AU$653
includes taxes & fees
23 Oct - 24 Oct
Gulfside 2BR Condo–Silver Sands #257S
Marina
Bayfront Condo Walkable to Everything. Unit 3
Bayfront Condo Walkable to Everything. Unit 3
9.6 out of 10, Exceptional, (21)
"Nice location, clean"
United States
Al H.
The price is AU$678
includes taxes & fees
23 Oct - 24 Oct
Bayfront Condo Walkable to Everything. Unit 3
On the beach, sun-loungers, beach towels
Beachfront Condo on LBK!
Beachfront Condo on LBK!
10.0 out of 10, Exceptional, (83)
"Charming place with a fantastic beach!"
United States
Mike M.
The price is AU$676
includes taxes & fees
5 Nov - 6 Nov
Beachfront Condo on LBK!
Beach
Superb Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants
Superb Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants
9.8 out of 10, Exceptional, (111)
"I stayed 1 night with 2 of my friends and honestlyEverything was amazing, place was super clean, the host was super quick to answer my questions and I would for sure booked again."
United States
Jenifer M.
The price is AU$464
includes taxes & fees
27 Oct - 28 Oct
Superb Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants
Terrace/patio
Siesta Key Condo: Beach, Pool & Village Fun!
Siesta Key Condo: Beach, Pool & Village Fun!
8.8 out of 10, Excellent, (9)
"My family of three stayed here for a quick weekend and loved how close it was to all the restaurants and the short walk to the beach. We parked our rental at check in and didn’t use it until we packed up to leave. We will definitely stay here again when we come back!"
United States
Drew B.
The price is AU$542
includes taxes & fees
28 Oct - 29 Oct
Siesta Key Condo: Beach, Pool & Village Fun!
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
"We didn't spend much time there except to sleep."
William 1-night trip
Posted 3 days ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
2,143
Accommodation
3764 Condo Rentals
Lowest Price
AU$182
Highest Price
AU$829

Frequently asked questions

How much do condos in Osprey cost?
The price range for condos in Osprey is AU$182 to AU$829 per night. Whatever your budget, you'll find something that fits the bill — as well as your whole squad! 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.
How many condos are there in Osprey?
Osprey has 3764 condos. To help you book the perfect digs, use our filters to search for the perks or amenities you need.
What are the best cheap condos in Osprey?
Captiva Beach Resort is one of the most affordable condos in Osprey and offers premium bedding and a pillowtop mattress. Another popular choice that's easy on the wallet is Hyatt Fractional #402 - 2 Bedroom Condo. Conveniences here include a swimming pool and free WiFi. Rates for condos start from AU$182 per night. If you're exploring Osprey and want to stay within your budget, there are many fun and free attractions to add to your itinerary. Siesta Key Beach and Venice Beach are always 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.
What is there to do in Osprey near my condo?
There are loads of superb things to see and do in Osprey. Head for big attractions like Siesta Key Beach, Venice Beach and Turtle Beach. Nokomis Beach, Crescent Beach and Manasota Beach are other must-do's.