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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Featured Condo Rentals in Osprey

Our top choices for Osprey condo rentals

Chadwick Cove Resort & Marina
Property grounds

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (11)
"Nic place to stay and enjoy the area"
The price is AU$834
includes taxes & fees
9 Sept - 10 Sept
Chadwick Cove Resort & Marina
Cozy beach house! Just steps away from the world-class Manasota beach
Sun-loungers, beach towels

Cozy beach house! Just steps away from the world-class Manasota beach

3.5 star property
9.8 out of 10, Exceptional, (6)
"Great place. "
The price is AU$651
includes taxes & fees
3 Sept - 4 Sept
Cozy beach house! Just steps away from the world-class Manasota beach
Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA
On the beach

Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA

8.8 out of 10, Excellent, (84)
"Gorgeous location, the beach was exceptional and the area was quiet and felt secluded. The condo was a bit shabby but clean and had everything we needed. "
The price is AU$492
includes taxes & fees
3 Sept - 4 Sept
Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA
Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool
A heated pool

Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool

9.0 out of 10, Wonderful, (21)
"Great stay. Great place."
The price is AU$485
includes taxes & fees
3 Sept - 4 Sept
Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool
Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1127)
"2nd time and excellent as always..close to the beach and great surroundings "
Captiva Beach Resort
The Sapphire Suite 1Bed/1Bath
Terrace/patio

The Sapphire Suite 1Bed/1Bath

9.8 out of 10, Exceptional, (82)
"We loved our stay here, it was a perfect location with lots to do within even walking distance! "
The price is AU$223
includes taxes & fees
15 Sept - 16 Sept
The Sapphire Suite 1Bed/1Bath
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
Property grounds

Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock

9.8 out of 10, Exceptional, (35)
"The property was very nice and convenient. We really enjoyed our stay and would come again. "
The price is AU$513
includes taxes & fees
11 Sept - 12 Sept
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
Riverside Oasis 1Bed/1Bath
Exterior detail

Riverside Oasis 1Bed/1Bath

9.4 out of 10, Exceptional, (34)
"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. "
The price is AU$181
includes taxes & fees
11 Sept - 12 Sept
Riverside Oasis 1Bed/1Bath
*Charming 2bed 2 bath 6 mins from IMG*
Beach nearby

*Charming 2bed 2 bath 6 mins from IMG*

9.6 out of 10, Exceptional, (21)
"Great place, spacious for 6 adults, clean, comfortable, organized with all the amenities one would need. Everything was simple from check in to check out. The queen-size air mattress fits seamlessly in the living room's common area and comes equipped with all necessary bedding to ensure a comfortable and restful experience.​ I would stay again!"
The price is AU$552
includes taxes & fees
4 Sept - 5 Sept
*Charming 2bed 2 bath 6 mins from IMG*
5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..
Sun-loungers, beach towels

5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..

9.6 out of 10, Exceptional, (27)
"Excellent location and really nice atmosphere"
The price is AU$648
includes taxes & fees
15 Sept - 16 Sept
5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..
Shorewalk Sunny Bella Rosa- 2 heated Jacuzzis & pools near IMG/beaches
Sun-loungers, beach towels

Shorewalk Sunny Bella Rosa- 2 heated Jacuzzis & pools near IMG/beaches

9.8 out of 10, Exceptional, (87)
"We were in town for IMG Academy graduation. Perfect location, great condo, and great communication with the host. Would rent again! "
The price is AU$389
includes taxes & fees
15 Sept - 16 Sept
Shorewalk Sunny Bella Rosa- 2 heated Jacuzzis & pools near IMG/beaches
Fabulous Shorewalk Palms Heaven condo-2 heated hot tubs & pools near IMG/beaches
Outdoor dining

Fabulous Shorewalk Palms Heaven condo-2 heated hot tubs & pools near IMG/beaches

10.0 out of 10, Exceptional, (24)
"Great spot, very convenient location."
The price is AU$399
includes taxes & fees
15 Sept - 16 Sept
Fabulous Shorewalk Palms Heaven condo-2 heated hot tubs & pools near IMG/beaches
Siesta Key Condo: Beach, Pool & Village Fun!
Terrace/patio

Siesta Key Condo: Beach, Pool & Village Fun!

8.6 out of 10, Excellent, (8)
"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!"
The price is AU$568
includes taxes & fees
8 Sept - 9 Sept
Siesta Key Condo: Beach, Pool & Village Fun!
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Property grounds

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

9.4 out of 10, Exceptional, (130)
"Loved how close it is to siesta key beach"
The price is AU$553
includes taxes & fees
11 Sept - 12 Sept
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Smart TV, books

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

9.8 out of 10, Exceptional, (95)
"Lovely unit and the perfect location. Short walk to the beach and easy to get to the shopping/eating areas. "
The price is AU$646
includes taxes & fees
26 Sept - 27 Sept
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Modern Coastal 2/2 condo w/pool 6 mins to IMG
Beach nearby

Modern Coastal 2/2 condo w/pool 6 mins to IMG

10.0 out of 10, Exceptional, (25)
"Had a great time and the pool are was super fun!"
The price is AU$556
includes taxes & fees
4 Sept - 5 Sept
Modern Coastal 2/2 condo w/pool 6 mins to IMG
5 minutes drive to nr Siesta Key 1/1 Large condo. The pool heated
Beach towels

5 minutes drive to nr Siesta Key 1/1 Large condo. The pool heated

10.0 out of 10, Exceptional, (12)
"Perfect little spot to enjoy Sarasota. We will return."
The price is AU$473
includes taxes & fees
15 Sept - 16 Sept
5 minutes drive to nr Siesta Key 1/1 Large condo. The pool heated
Charming Longboat Key Bungalow with beach access minutes away…
Sun-loungers

Charming Longboat Key Bungalow with beach access minutes away…

2.0 star property
9.4 out of 10, Exceptional, (12)
"Very cute place. It was in a great spot for easy access to the beach and restaurants. "
The price is AU$607
includes taxes & fees
3 Sept - 4 Sept
Charming Longboat Key Bungalow with beach access minutes away…
Bayfront Condo Walkable to Everything. Unit 3
Marina

Bayfront Condo Walkable to Everything. Unit 3

9.6 out of 10, Exceptional, (20)
"Nice location, clean"
The price is AU$690
includes taxes & fees
3 Sept - 4 Sept
Bayfront Condo Walkable to Everything. Unit 3
Beautifully furnished condo
Sun-loungers, beach towels

Beautifully furnished condo

9.8 out of 10, Exceptional, (136)
"Excellent location very close and convenient to everything. Condo was very nice. Will definitely stay there again!"
The price is AU$391
includes taxes & fees
8 Sept - 9 Sept
Beautifully furnished condo
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

Find out more about Osprey

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
Accommodation
3739 Condo Rentals
Lowest Price
AU$485
Highest Price
AU$849

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much do condos in Osprey cost?
The price range for condos in Osprey is AU$485 to AU$849 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 3739 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$485 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.