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

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Our top choices for Osprey condo rentals

1. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,294 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is CA $218
CA $270 total
includes taxes & fees
Aug 10 - Aug 11
Captiva Beach Resort

2. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (657 reviews)
"The beach is right there, very clean and nice place."
United States
Maryna
The price is CA $258
CA $292 total
includes taxes & fees
Aug 27 - Aug 28
A Beach Retreat

3. 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 CA $251
CA $765 total
includes taxes & fees
Aug 11 - Aug 12
Turtle Nest

4. 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 CA $280
CA $665 total
includes taxes & fees
Aug 2 - Aug 3
2BR Beach Style w Pool Beach Club Siesta 204C RVA

5. 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 CA $375
CA $621 total
includes taxes & fees
Aug 6 - Aug 7
Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach

6. Turquoise Water & Soft White Sand - The Beach Club at Siesta Key #104A by RVA

Turquoise Water & Soft White Sand - The Beach Club at Siesta Key #104A by RVA
South Village
9.0 out of 10, Wonderful, (78 reviews)
"Wonderful location, clean aparment, pool and jaccuzi were very nice, but the WiFi was terrible, very very slow."
United States
Alexis
The price is CA $279
CA $663 total
includes taxes & fees
Aug 2 - Aug 3
Turquoise Water & Soft White Sand - The Beach Club at Siesta Key #104A by RVA

7. Jetties Pointe Cottage #3 - 408 “Casey Key”

Jetties Pointe Cottage #3 - 408 “Casey Key”
Casey Key
9.4 out of 10, Exceptional, (29 reviews)
"Condo was very clean and equipped with everything that was needed for a very enjoyable vacation. "
United States
Nancy T.
The price is CA $368
CA $763 total
includes taxes & fees
Aug 5 - Aug 6
Jetties Pointe Cottage #3 - 408 “Casey Key”

8. 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)
"Facilities were clean and well appointed. Close enough to walk to beach and several restaurants/shops. "
United States
Anonymous traveller
The price is CA $286
CA $674 total
includes taxes & fees
Aug 11 - Aug 12
Breathtaking Turquoise Gulf Water-The Beach Club at Siesta Key #104D by RVA

9. House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!
South Village
9.2 out of 10, Wonderful, (142 reviews)
"Accommodations were perfect for our family of 6. Extremely convenient to have private beach access along with chairs and ability to get umbrellas for shade."
United States
James N.
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

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 CA $210
CA $451 total
includes taxes & fees
Aug 2 - Aug 3
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

11. 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
The price is CA $385
CA $759 total
includes taxes & fees
Aug 3 - Aug 4
Renovated condo with easy beach access on Siesta

12. 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 CA $258
CA $866 total
includes taxes & fees
Aug 19 - Aug 20
Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

13. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 1bdr

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 1bdr
Siesta Key Village
9.2 out of 10, Wonderful, (7 reviews)
"Loved having all of the beach supplies provided! Also, location was ideal. Very close to Siesta Key Village. "
United States
Tracy F.
The price is CA $839
CA $1,069 total
includes taxes & fees
Aug 1 - Aug 2
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 1bdr

14. 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, (99 reviews)
"Great location"
United States
Daphane
The price is CA $345
CA $582 total
includes taxes & fees
Aug 14 - Aug 15
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

15. 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 CA $279
CA $472 total
includes taxes & fees
Aug 4 - Aug 5
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

16. 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, (62 reviews)
"Great!"
United States
Douglas
The price is CA $291
CA $682 total
includes taxes & fees
Aug 23 - Aug 24
The Beach Club at Siesta Key #106D Resort by RVA

17. 2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA

2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
South Village
9.2 out of 10, Wonderful, (74 reviews)
"Great short stay. Close walk to the beach! "
United States
Tera S.
The price is CA $263
CA $644 total
includes taxes & fees
Aug 4 - Aug 5
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA

18. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"We found this property to be delightful. We loved the balcony for enjoying our evenings. I would have liked to see a table on the balcony for eating at, it is FL, and I wanted to sit outside for my meals. It was a very close walk to the beach, the pool and hot tub were in excellent working condition. We enjoyed the property. We had a problem, but they had maintenance there within an hour to fix it, I call that a win for the property. "
United States
Jackie J.
The price is CA $282
CA $669 total
includes taxes & fees
Aug 5 - Aug 6
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

19. In the heart of Siesta Key Village | Walk to Beach | Fully renovated & remodeled

In the heart of Siesta Key Village | Walk to Beach | Fully renovated & remodeled
Siesta Key Village
9.4 out of 10, Exceptional, (24 reviews)
"Great place to stay the pool was amazing, warm quiet, and walking distance to the restaurants, shopping and to the beach. We had an amazing week stay"
United States
Tawnya s.
The price is CA $274
CA $882 total
includes taxes & fees
Aug 13 - Aug 14
In the heart of Siesta Key Village | Walk to Beach | Fully renovated & remodeled

20. Fully Renovated Beachside Getaway with Heated Pool – Walk to Restaurants

Fully Renovated Beachside Getaway with Heated Pool – Walk to Restaurants
Siesta Key
9.2 out of 10, Wonderful, (93 reviews)
"Great place to stay"
United States
Skyler A.
The price is CA $426
CA $773 total
includes taxes & fees
Aug 5 - Aug 6
Fully Renovated Beachside Getaway with Heated Pool – Walk to Restaurants
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

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
3,043
Accommodation
3674 Condo Rentals
Lowest Price
CA $270
Highest Price
CA $1,069

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from CA $270 to CA $1,069 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 travelling 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 3674 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 CA $270 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 favourite 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 11 kilometres 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 8 kilometres from the centre 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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