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

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.
The price is AU$797
includes taxes & fees
5 Oct - 6 Oct
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, (1,314 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is AU$278
includes taxes & fees
8 Oct - 9 Oct
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.
The price is AU$440
includes taxes & fees
8 Oct - 9 Oct
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, (686 reviews)
"Great stay!!"
United States
Genghis
The price is AU$308
includes taxes & fees
4 Oct - 5 Oct
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.
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.
The price is AU$532
includes taxes & fees
4 Oct - 5 Oct
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
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.
The price is AU$557
includes taxes & fees
11 Oct - 12 Oct
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.
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.
The price is AU$383
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AU$423
includes taxes & fees
24 Oct - 25 Oct
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
The price is AU$563
includes taxes & fees
4 Oct - 5 Oct
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.
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.
The price is AU$624
includes taxes & fees
3 Oct - 4 Oct
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.
The price is AU$521
includes taxes & fees
7 Oct - 8 Oct
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.
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.
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
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.
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.
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

Tropical Breeze Resort

Tropical Breeze Resort

8/10 Good
"The resort rooms are spread around Siesta Village. Our room was not directly attached to the hotel. The location is fantastic, walking distance to the beach and restaurants. The room was very nice and clean. The only complaint we had was that there was no sound proofing between floors and we were kept awake by footsteps all night long."
Lisa 2-night trip
Posted 1 hour ago
Tropical Breeze Resort

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
912
Accommodation
3554 Condo Rentals
Lowest Price
AU$278
Highest Price
AU$797

Frequently asked questions

How much do condos in Osprey cost?
The price range for condos in Osprey is AU$278 to AU$797 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 3554 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$278 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.