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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Osprey condo rentals

A covered patio with a sofa, a table, and potted plants.

1. Turtle Nest

Turtle Nest
Sarasota
10.0 out of 10, Exceptional, (12 reviews)
"Great place- relaxed vibe"
United States
zachary p.
$472 nightly
The price is $526
Nov 2 - Nov 3
Total with taxes and fees
Turtle Nest
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

2. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,328 reviews)
"We liked the clean room, friendly staff, close to the beach and outdoor amenities."
United States
Andriy
$188 nightly
The price is $210
Nov 10 - Nov 11
Total with taxes and fees
Captiva Beach Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

3. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (695 reviews)
"Enjoyed our stay"
United States
Robin
$205 nightly
The price is $231
Nov 4 - Nov 5
Total with taxes and fees
A Beach Retreat
A beach with tall grasses and a sunset.

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.
$297 nightly
The price is $331
Nov 2 - Nov 3
Total with taxes and fees
Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key
A beach path leading to the sea with grass on either side.

5. Jetties Pointe Cottage #2 - 408 “Casey Key”

Jetties Pointe Cottage #2 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (15 reviews)
"Cute little beach cottage! It was perfect for my little family of 4. The location was great and the swings overlooking the beach were wonderful. "
United States
Kirstie C.
$344 nightly
The price is $383
Oct 31 - Nov 1
Total with taxes and fees
Jetties Pointe Cottage #2 - 408 “Casey Key”
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

6. 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, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
$226 nightly
The price is $252
Nov 1 - Nov 2
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A balcony with a view of a pond, surrounded by trees and a grassy area.

7. 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.
$218 nightly
The price is $244
Nov 1 - Nov 2
Total with taxes and fees
The Perfect Shiny Condo
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

8. The Beach Club at Siesta Key #106D Resort by RVA

The Beach Club at Siesta Key #106D Resort by RVA
South Village
9.4 out of 10, Exceptional, (63 reviews)
"Close to beach and easy with two kids. Had a great time!"
United States
Kelley B.
$432 nightly
The price is $481
Oct 30 - Oct 31
Total with taxes and fees
The Beach Club at Siesta Key #106D Resort by RVA
A rooftop lounge with a fire feature, seating, and a view of the cityscape.

9. 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.
$281 nightly
The price is $313
Nov 2 - Nov 3
Total with taxes and fees
Heated Pool Apartment Near Siesta Key 1BR
A spacious room with a white ceiling fan, a beige sofa, a dining table with chairs, and large windows with blinds.

10. 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.
$383 nightly
The price is $427
Nov 1 - Nov 2
Total with taxes and fees
Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

11. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
9.0 out of 10, Wonderful, (81 reviews)
"Good"
United States
Gelsy
$386 nightly
The price is $430
Oct 30 - Oct 31
Total with taxes and fees
2BR Beach Style w Pool Beach Club Siesta 204C RVA
A beach with umbrellas, lounge chairs, and a building in the background.

12. 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.
$337 nightly
The price is $376
Oct 30 - Oct 31
Total with taxes and fees
Have fun at our Sunny Beachside Retreat remodeled head to toe!
A beach with tall grasses and a sunset.

13. Renovated condo with easy beach access on Siesta

Renovated condo with easy beach access on Siesta
Siesta Key
9.2 out of 10, Wonderful, (80 reviews)
"The place was cute and clean. It was a nice stay:)"
United States
Angie
$401 nightly
The price is $447
Oct 30 - Oct 31
Total with taxes and fees
Renovated condo with easy beach access on Siesta
A beach with white sand, a clear blue sky, and tall grasses.

14. 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.
$430 nightly
The price is $480
Nov 1 - Nov 2
Total with taxes and fees
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
A beach with a lifeguard tower, a blue umbrella, and a few people.

15. 5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..

5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..
Sarasota
9.4 out of 10, Exceptional, (28 reviews)
"Excellent location and really nice atmosphere"
United States
Eduardo V.
$373 nightly
The price is $416
Nov 2 - Nov 3
Total with taxes and fees
5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..
A bedroom with a bed, a TV, a window, and a view of the outside.

16. Ivory & Ocean •walk to Lido beach •private patio

Ivory & Ocean •walk to Lido beach •private patio
Lido Key
10.0 out of 10, Exceptional, (6 reviews)
$220 nightly
The price is $230
Oct 31 - Nov 1
Total with taxes and fees
Ivory & Ocean •walk to Lido beach •private patio
A room with a sliding glass door leading to an outdoor area with a pool and chairs. There is a brown leather sofa with patterned cushions and a framed picture on the wall.

17. 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.
$329 nightly
The price is $367
Nov 18 - Nov 19
Total with taxes and fees
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

18. The Beach Club at Siesta Key #106A Resort by RVA

The Beach Club at Siesta Key #106A Resort by RVA
South Village
9.0 out of 10, Wonderful, (68 reviews)
"Our family had a blast - great beach and pools."
United States
Nicholas M.
$430 nightly
The price is $480
Nov 1 - Nov 2
Total with taxes and fees
The Beach Club at Siesta Key #106A Resort by RVA
A beach with a building in the background during sunset.

19. Canalfront Siesta key entire King suite

Canalfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (13 reviews)
"Great location, spacious parking, clean."
United States
Norma C.
$283 nightly
The price is $315
Nov 15 - Nov 16
Total with taxes and fees
Canalfront Siesta key entire King suite
Beach

20. 5 Minutes from Siesta Key!

5 Minutes from Siesta Key!
Sarasota
9.4 out of 10, Exceptional, (53 reviews)
"Wonderful place to stay, super clean and comfortable. Communication was great."
United States
Cameron W.
$328 nightly
The price is $367
Nov 22 - Nov 23
Total with taxes and fees
5 Minutes from Siesta Key!
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

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"Nice location. Tiki bar was ok, decent convo with visitors. Training new staff was an issue but she persevered and all was good. Ice machine broken, only 1 on property. We would stay there again."
Bryan 1-night trip
Posted 4 hours ago
Golden Host Resort - Sarasota

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
2,567
Accommodation
3697 Condo Rentals
Lowest Price
$210
Highest Price
$526

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $210 to $526 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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