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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Osprey condo rentals

Terrace/patio

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 £410
includes taxes & fees
18 Aug - 19 Aug
Turtle Nest
Front of property – evening/night

2. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,297 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is £148
includes taxes & fees
20 Aug - 21 Aug
Captiva Beach Resort
Beachside One Bedroom Suite | Premium bedding, pillow-top beds, iron/ironing board (on request)

3. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (665 reviews)
"Lovely place on a family beach."
United States
Robert
The price is £154
includes taxes & fees
27 Aug - 28 Aug
A Beach Retreat
Property grounds

4. Heated Pool Apartment Near Siesta Key 1BR

Heated Pool Apartment Near Siesta Key 1BR
Sarasota
9.2 out of 10, Wonderful, (47 reviews)
"Great location for my interests. My life long indoor cat loved the lanai.The host was kind and helpful in local suggestions .The accommodations was clean and comfortable. I would not hesitate to return . "
United States
Kathy B.
The price is £235
includes taxes & fees
14 Sept - 15 Sept
Heated Pool Apartment Near Siesta Key 1BR
Beach nearby

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, (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 £189
includes taxes & fees
18 Aug - 19 Aug
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
Property grounds

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

Jetties Pointe Cottage #6 - 408 “Casey Key”
Casey Key
10.0 out of 10, Exceptional, (16 reviews)
"Unique property, right on the beach . Great view from balcony Plan to visit again"
United States
Tonya
The price is £294
includes taxes & fees
25 Aug - 26 Aug
Jetties Pointe Cottage #6 - 408 “Casey Key”
Beach nearby, beach umbrellas

7. 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, (89 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
The price is £271
includes taxes & fees
16 Aug - 17 Aug
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
Sun-loungers, beach towels

8. Canalfront Siesta key entire King suite

Canalfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (12 reviews)
"Great location, spacious parking, clean."
United States
Norma C.
The price is £217
includes taxes & fees
13 Sept - 14 Sept
Canalfront Siesta key entire King suite
Beach nearby, sun-loungers, beach towels, snorkelling

9. Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key
South Village
9.4 out of 10, Exceptional, (38 reviews)
"It was a great location with easy access to the pool, beach and entertainment! The place was clean and nice, perfect for our family!"
United States
Emily
The price is £437
includes taxes & fees
19 Aug - 20 Aug
Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key
Beach nearby

10. Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach

Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach
Siesta Key
9.0 out of 10, Wonderful, (79 reviews)
"Nice place, great location,pool,and was nice having 2 grills on the property. "
United States
Nicholas H.
The price is £300
includes taxes & fees
19 Aug - 20 Aug
Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach
Beach nearby

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

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
8.8 out of 10, Excellent, (80 reviews)
"Beautiful place"
United States
Chad
The price is £344
includes taxes & fees
16 Aug - 17 Aug
2BR Beach Style w Pool Beach Club Siesta 204C RVA
Beach nearby, beach umbrellas

12. 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, (67 reviews)
"Our family had a blast - great beach and pools."
United States
Nicholas M.
The price is £352
includes taxes & fees
18 Aug - 19 Aug
The Beach Club at Siesta Key #106A Resort by RVA
Beach nearby

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

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Siesta Key
9.4 out of 10, Exceptional, (141 reviews)
"Excellent location right across street from beach. Parking spaces are tight, and there is some loud music in surrounding units or businesses."
United States
Michael D.
The price is £259
includes taxes & fees
23 Aug - 24 Aug
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Beach nearby

14. Siesta Key Condo: Beach, Pool & Village Fun!

Siesta Key Condo: Beach, Pool & Village Fun!
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 £258
includes taxes & fees
20 Aug - 21 Aug
Siesta Key Condo: Beach, Pool & Village Fun!
On the beach

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

Jetties Pointe Cottage #2 - 408 “Casey Key”
Casey Key
9.4 out of 10, Exceptional, (13 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 £299
includes taxes & fees
18 Aug - 19 Aug
Jetties Pointe Cottage #2 - 408 “Casey Key”
On the beach

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

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.8 out of 10, Exceptional, (32 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
The price is £299
includes taxes & fees
16 Aug - 17 Aug
Jetties Pointe Cottage #5 - 408 “Casey Key”
Beach nearby, beach umbrellas

17. 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 £268
includes taxes & fees
25 Aug - 26 Aug
Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
Beach nearby, beach umbrellas

18. 1BR Pool-View Condo at The Beach Club on Siesta Key | Steps to the beach

1BR Pool-View Condo at The Beach Club on Siesta Key | Steps to the beach
South Village
8.8 out of 10, Excellent, (88 reviews)
"Clean and short easy walk to the beach. "
United States
Maureen S.
The price is £274
includes taxes & fees
16 Aug - 17 Aug
1BR Pool-View Condo at The Beach Club on Siesta Key | Steps to the beach
Beach nearby, beach umbrellas

19. Romantic Getaway Beach Club Siesta 202B by RVA

Romantic Getaway Beach Club Siesta 202B by RVA
South Village
8.8 out of 10, Excellent, (57 reviews)
"Peaceful getaway. Throughly enjoyed the stay. "
United States
Anonymous traveller
The price is £262
includes taxes & fees
27 Aug - 28 Aug
Romantic Getaway Beach Club Siesta 202B by RVA
Beach nearby, beach umbrellas

20. 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, (91 reviews)
"Great location and easy access to the beach."
United States
Erica B.
The price is £261
includes taxes & fees
26 Aug - 27 Aug
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Fantastic staff and amenities"
Alexander 7-night trip
Posted 2 hours ago
Kompose Boutique Hotel

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,564
Accommodation
3650 Condo Rentals
Lowest Price
£148
Highest Price
£437

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from £148 to £437 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 3650 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 £148 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.