A marina with docked boats, a wooden bridge, and a building with a red roof.

Search and Rent Osprey Condos

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Our top choices for Osprey condo rentals

1. Turtle Nest

Turtle Nest
Sarasota
10.0 out of 10, Exceptional, (12 reviews)
"Great place- relaxed vibe"
United States
zachary p.
$446 nightly
The price is $502
Nov 15 - Nov 16
Total with taxes and fees
Turtle Nest

2. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (701 reviews)
"Enjoyed our stay"
United States
Robin
$205 nightly
The price is $231
Dec 6 - Dec 7
Total with taxes and fees
A Beach Retreat

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,336 reviews)
"Great location that's very close to the beach, large and clean room with a kitchenette, and very helpful and friendly staff. Loved our stay here!"
United States
Bob
$188 nightly
The price is $210
Nov 17 - Nov 18
Total with taxes and fees
Captiva Beach Resort

4. Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key

Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key
Siesta Key
9.0 out of 10, Wonderful, (42 reviews)
"Siesta Heron is a gem! We loved having morning coffee on the deck by the water, the heated pool and the easy access to the trolley. Great location. The unit was clean and the hosts were extremely responsive and helpful!"
United States
Carrie B.
$285 nightly
The price is $319
Nov 18 - Nov 19
Total with taxes and fees
Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key

5. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
$229 nightly
The price is $256
Nov 17 - Nov 18
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

6. Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"We enjoyed it. All was as described"
United States
Pamela S.
$245 nightly
The price is $276
Nov 15 - Nov 16
Total with taxes and fees
Bright & Beachy–Beach Club Siesta Key 100A by RVA

7. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
$235 nightly
The price is $265
Nov 15 - Nov 16
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

8. The Perfect Shiny Condo

The Perfect Shiny Condo
Sarasota
9.4 out of 10, Exceptional, (20 reviews)
"The property could probably use some updating but the apartment was clean and had the needed essentials. Close and convenient driving distance to beaches. Good place to stay if you’re in Sarasota."
United States
Janneth A.
$215 nightly
The price is $241
Nov 16 - Nov 17
Total with taxes and fees
The Perfect Shiny Condo

9. 2BR Beach & Trolley–Beach Club Siesta 204B by RVA

2BR Beach & Trolley–Beach Club Siesta 204B by RVA
South Village
8.6 out of 10, Excellent, (48 reviews)
"Was exactly as advertised. When I needed help the hosts were responsive. I have stayed there twice. Would stay again."
United States
Ben B.
$331 nightly
The price is $373
Nov 15 - Nov 16
Total with taxes and fees
2BR Beach & Trolley–Beach Club Siesta 204B by RVA

10. Heated Pool Apartment Near Siesta Key 1BR

Heated Pool Apartment Near Siesta Key 1BR
Sarasota
9.2 out of 10, Wonderful, (47 reviews)
"The condo is small but it was clean and we had a great time. Short drive to Siesta Key public beach and close to shopping. Doris was a great host and answered any questions we had."
United States
Melissa M.
$261 nightly
The price is $292
Nov 16 - Nov 17
Total with taxes and fees
Heated Pool Apartment Near Siesta Key 1BR

11. Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks

Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks
Siesta Key
9.2 out of 10, Wonderful, (43 reviews)
"Excellent host, great location. I will come back again."
United States
Lu V.
$356 nightly
The price is $399
Nov 18 - Nov 19
Total with taxes and fees
Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks

12. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"Great beach! "
United States
Annie B.
$353 nightly
The price is $397
Nov 15 - Nov 16
Total with taxes and fees
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

13. Blue Seas & Sand 2BR Beach Club Siesta 200C by RVA

Blue Seas & Sand 2BR Beach Club Siesta 200C by RVA
South Village
9.2 out of 10, Wonderful, (63 reviews)
"We had the best time staying here! Perfect location and nice size rooms!"
United States
Baylee J.
$344 nightly
The price is $387
Nov 15 - Nov 16
Total with taxes and fees
Blue Seas & Sand 2BR Beach Club Siesta 200C by RVA

14. Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Siesta Key
9.4 out of 10, Exceptional, (100 reviews)
"The place was excellent!!! Very beautiful and close to the beach. Super cozy. It was perfect and just what I had in mind."
United States
Amy P.
$308 nightly
The price is $345
Nov 15 - Nov 16
Total with taxes and fees
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

15. Canalfront Siesta key entire King suite

Canalfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (14 reviews)
"Great location, spacious parking, clean."
United States
Norma C.
$237 nightly
The price is $265
Dec 2 - Dec 3
Total with taxes and fees
Canalfront Siesta key entire King suite

16. Jetties Pointe Cottage #6 - 408 “Casey Key”

Jetties Pointe Cottage #6 - 408 “Casey Key”
Casey Key
10.0 out of 10, Exceptional, (19 reviews)
"Unique property, right on the beach . Great view from balcony Plan to visit again"
United States
Tonya
$351 nightly
The price is $392
Nov 21 - Nov 22
Total with taxes and fees
Jetties Pointe Cottage #6 - 408 “Casey Key”

17. 5 Minutes from Siesta Key!

5 Minutes from Siesta Key!
Sarasota
9.4 out of 10, Exceptional, (54 reviews)
"Very cute place with a beachy vibe, super great location. Owner was very quick to respond to any questions. Thank you Tricia and Tom, we really enjoyed our stay!!"
United States
Tamara C.
$303 nightly
The price is $339
Nov 22 - Nov 23
Total with taxes and fees
5 Minutes from Siesta Key!

18. Updated unit with easy beach access on Siesta Key

Updated unit with easy beach access on Siesta Key
Siesta Key
9.2 out of 10, Wonderful, (89 reviews)
"Good location, everything was clean. Enjoyed beach access. Will stay again."
United States
Pat G.
$389 nightly
The price is $434
Dec 1 - Dec 2
Total with taxes and fees
Updated unit with easy beach access on Siesta Key

19. Have fun at our Sunny Beachside Retreat remodeled head to toe!

Have fun at our Sunny Beachside Retreat remodeled head to toe!
South Village
9.8 out of 10, Exceptional, (16 reviews)
"Place was clean and nice.. deff good location close to beach and pool will be back soon"
United States
Oscar G.
$344 nightly
The price is $385
Nov 17 - Nov 18
Total with taxes and fees
Have fun at our Sunny Beachside Retreat remodeled head to toe!

20. Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!

Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
South Village
10.0 out of 10, Exceptional, (22 reviews)
"The stay was nice!"
United States
John S.
$444 nightly
The price is $495
Nov 17 - Nov 18
Total with taxes and fees
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
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

Osprey Condo Rentals information

Number of reviews
2,803
Accommodation
3697 Condo Rentals
Lowest Price
$210
Highest Price
$502

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $210 to $502 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 traveling 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 vacation dates and then pick from 3697 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.
What are the best cheap condos in Osprey?
With condos starting from $210 per night, you may be tempted to stay a little longer in Osprey! One property that's easy on the pocket is Captiva Beach Resort. It comes with the layout you're looking for as well as pillow top mattresses and a swimming pool. Another cost-effective pick is Bs 1350 - #1 Siesta And Crescent Beach Are Walking Distance Away, which offers a lake view and a sauna. If you prefer to save your hard-earned cash and still experience the best of Osprey, add a couple of fun and free attractions to your must-do list. Siesta Key Beach and Venice Beach will keep you on the go. 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 condos in Osprey?
Get comfortable at Venice Beach Villas, a 3-star option just a quick drive from downtown. Amenities here include a barbecue grill and a swimming pool. Another family-friendly condo is Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village. A deck and a lanai help make this 3-star property a favorite among guests. Once you've checked in and unpacked, there's a host of family-friendly attractions to visit around Osprey. Siesta Key Beach and Venice Beach are two of our top suggestions.
Are there any 5-star condos in Osprey?
Although there are no 5-star condos in Osprey, there are 4-star accommodations that have what you're looking for. Located about 7 miles from the downtown area, Gulf Holiday By Beachside Management comes with concierge services and a swimming pool. Another upscale retreat is Excelsior Beach To Bay - Bayside. It's roughly 5 miles from the center of Osprey and has amenities like a swimming pool and a deck.
Why book your condo in Osprey with Expedia?
With Expedia, it's a cinch to find your ideal condo in Osprey. After someplace luxurious? Make the most of our filters to search for properties that have a 5-star rating. If you have a set budget, select how much you're willing to spend and then browse our amazing options. We'll help you find the perfect fit whatever your escape looks like.
How can I find cheap condos in Osprey?
With Expedia's user-friendly filter tool, comparing cheap condos in Osprey is a snap. To discover properties that'll make your wallet happy, refine your search by amenities, budget and star rating.
What is there to do in Osprey near my condo?
If you'd like to make the most of your time in Osprey, be sure to stop by Oscar Scherer State Park. It's a hit with locals and travelers alike.

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