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

Search Condos Rentals in Osprey

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

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)
"I absolutely loved the location. It was quiet and views of the water"
United States
Felicia
The price is £423
includes taxes & fees
6 Oct - 7 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, (1,312 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is £146
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 £213
includes taxes & fees
30 Sept - 1 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, (685 reviews)
"Great stay!!"
United States
Genghis
The price is £161
includes taxes & fees
8 Oct - 9 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.
The price is £265
includes taxes & fees
30 Sept - 1 Oct
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 £269
includes taxes & fees
30 Sept - 1 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
The price is £323
includes taxes & fees
30 Sept - 1 Oct
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 £298
includes taxes & fees
3 Oct - 4 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 price is £339
includes taxes & fees
30 Sept - 1 Oct
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 £219
includes taxes & fees
1 Oct - 2 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 £221
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 £285
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 £332
includes taxes & fees
30 Sept - 1 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 £285
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.
The price is £253
includes taxes & fees
2 Oct - 3 Oct
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.
The price is £537
includes taxes & fees
10 Oct - 11 Oct
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
The price is £265
includes taxes & fees
30 Sept - 1 Oct
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.
The price is £274
includes taxes & fees
1 Oct - 2 Oct
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.
The price is £329
includes taxes & fees
30 Sept - 1 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Amazing price for the niceness of the hotel. Great location too. Plenty of amenities but I didn't have time to use them. Staff was helpful and they even had a mini coffee shop. Only negative I could think of was no water fountains at all in the hotel, but there was water in the lobby for drinking."
Timothy 1-night trip
Posted less than an hour ago
Kompose Boutique Hotel

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,597
Accommodation
3617 Condo Rentals
Lowest Price
£146
Highest Price
£537

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from £146 to £537 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?
We recommend Venice Beach Villas. Kick back at this 3-star property which comes with a terrace and therapeutic mineral springs. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is another highly rated condo worth looking into. Spend your holiday at this popular 3-star option and you'll have access to amenities including a deck and a lanai. You can choose from multiple condos in Osprey with a total average guest review rating of 9.3.
How many condos are there in Osprey?
Work out your holiday dates and then pick from 3617 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?
Captiva Beach Resort is one of the best inexpensive condos in Osprey and includes pillow top mattresses and premium bedding. Another popular choice that's easy on the budget is Bs 1350 - #1 Siesta And Crescent Beach Are Walking Distance Away. It features a barbecue grill and a swimming pool. Rates for condos start from only £146 per night. If you want to save your hard-earned cash and still experience the best of Osprey, add a couple of awesome free attractions to your to-do list. Manasota Beach and Sarasota National Cemetery are always popular among visitors. 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?
Many visitors needing family-friendly condos in Osprey go for Venice Beach Villas. With a 3-star rating and amenities including therapeutic mineral springs and a barbecue grill, it'll feel like your home away from home. Or, consider 3-star Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village. A deck and a lanai help make it an ideal base for your Osprey getaway. Osprey has lots of family-friendly attractions to explore when the kids are getting restless. Manasota Beach and Heritage Oaks Golf and Country Club promise fun for everyone.
Are there any 5-star condos in Osprey?
You won't find any 5-star condos in Osprey. However, you will find some comfortable 4-star stays that have this feature. Check in to Gulf Holiday By Beachside Management, about 7 mi from downtown. a swimming pool and concierge services are a couple of the many conveniences included here. Jamaica Royale - 028 - 1 Bedroom Condo is another upmarket option. It comes with a furnished patio and a nearby seaside and is located around 6 mi from the centre of Osprey.
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 travellers alike.