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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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)
"I absolutely loved the location. It was quiet and views of the water"
United States
Felicia
$481 nightly
The price is $537
Sep 30 - Oct 1
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, (1,312 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
$153 nightly
The price is $171
Oct 1 - Oct 2
Total with taxes and fees
Captiva Beach Resort
A rooftop lounge with a fire feature, seating, and a view of the cityscape.

3. 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.
$246 nightly
The price is $274
Sep 30 - Oct 1
Total with taxes and fees
Heated Pool Apartment Near Siesta Key 1BR
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

4. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (685 reviews)
"Great stay!!"
United States
Genghis
$210 nightly
The price is $237
Sep 30 - Oct 1
Total with taxes and fees
A Beach Retreat
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

5. Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
South Village
8.8 out of 10, Excellent, (89 reviews)
"Great location and easy access to the beach."
United States
Erica B.
$306 nightly
The price is $341
Sep 30 - Oct 1
Total with taxes and fees
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
A beach with clear blue water and a sandy shore.

6. Beachfront Getaway in Siesta Key

Beachfront Getaway in Siesta Key
South Village
9.6 out of 10, Exceptional, (41 reviews)
"Our stay at Seacrest was great. It was just as described and more. Dior was a great host and promptly answered any questions we had. The location was great as well. "
United States
Nicholas W.
$310 nightly
The price is $346
Sep 30 - Oct 1
Total with taxes and fees
Beachfront Getaway in Siesta Key
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

7. 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
Sep 30 - Oct 1
Total with taxes and fees
2BR Beach Style w Pool Beach Club Siesta 204C RVA
A beach path leading to the sea with grass on either side.

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

Jetties Pointe Cottage #2 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (14 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 6 - Oct 7
Total with taxes and fees
Jetties Pointe Cottage #2 - 408 “Casey Key”
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

9. 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.
$404 nightly
The price is $450
Sep 30 - Oct 1
Total with taxes and fees
The Beach Club at Siesta Key #106A Resort by RVA
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

10. 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.
$260 nightly
The price is $290
Oct 1 - Oct 2
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A beach with a building in the background during sunset.

11. 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.
$251 nightly
The price is $281
Oct 24 - Oct 25
Total with taxes and fees
Canalfront Siesta key entire King suite
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.

12. 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)
"Great location"
United States
Daphane
$328 nightly
The price is $366
Oct 4 - Oct 5
Total with taxes and fees
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

13. Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!

Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!
Sarasota
9.8 out of 10, Exceptional, (38 reviews)
"Close to the beach. Loved having a pool to relax in. Great decor."
United States
Cassie N.
$482 nightly
The price is $541
Oct 18 - Oct 19
Total with taxes and fees
Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!
A beach with tall grasses and a sunset.

14. 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)
"Beds were hard, and the air conditioning did not work very well. It stayed around 78 the entire stay inside the condo. It was located at a great spot and over all was good except for beds and air."
United States
Jennifer A.
$395 nightly
The price is $440
Sep 30 - Oct 1
Total with taxes and fees
Updated unit with easy beach access on Siesta Key
A beach with a clear sky and calm sea.

15. Heart of Village: Dog-Friendly w/ Pool & Parking

Heart of Village: Dog-Friendly w/ Pool & Parking
Siesta Key Village
9.2 out of 10, Wonderful, (16 reviews)
"Love the place. Perfect location. Close to village, close to beach. Highly suggest and will definitely be back in the future. Host was very friendly and accommodating."
United States
Jeffrey B.
$334 nightly
The price is $352
Sep 30 - Oct 1
Total with taxes and fees
Heart of Village: Dog-Friendly w/ Pool & Parking
A beach with tall grasses and a sunset.

16. Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Siesta Key
9.2 out of 10, Wonderful, (145 reviews)
"We loved it!"
United States
John S.
$280 nightly
The price is $313
Oct 2 - Oct 3
Total with taxes and fees
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

17. Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village
Siesta Key Village
9.4 out of 10, Exceptional, (92 reviews)
"This property was very comfortable for our family of 3, everything was very clean, specially the towels and bed sheets, has perfect location, walking distance to the beach and the village which is lovely with plenty of restaurants, few ice cream shops, nice cafes, we had a great time staying in this apartment and will definitely recommend to family and friends"
United States
Maliuska R.
$608 nightly
The price is $679
Oct 10 - Oct 11
Total with taxes and fees
Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

18. Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (90 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
$306 nightly
The price is $341
Sep 30 - Oct 1
Total with taxes and fees
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

19. Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA

Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
South Village
9.0 out of 10, Wonderful, (76 reviews)
"Great stay. As advertised and very clean!"
United States
Seth S.
$305 nightly
The price is $340
Sep 30 - Oct 1
Total with taxes and fees
Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

20. Breathtaking Turquoise Gulf Water-The Beach Club at Siesta Key #104D by RVA

Breathtaking Turquoise Gulf Water-The Beach Club at Siesta Key #104D by RVA
South Village
9.0 out of 10, Wonderful, (85 reviews)
"Perfect location!"
United States
Tiffany L.
$392 nightly
The price is $437
Sep 30 - Oct 1
Total with taxes and fees
Breathtaking Turquoise Gulf Water-The Beach Club at Siesta Key #104D by RVA
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

Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

10/10 Excellent
"Hotel was very clean, room was perfect. Pool was a little cold but tolerable."
Doug 1-night trip
Posted less than an hour ago
Embassy Suites by Hilton Sarasota, FL

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,597
Accommodation
3697 Condo Rentals
Lowest Price
$171
Highest Price
$679

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $171 to $679 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 9.3. 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 $171 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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