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

Search Condos Rentals in Osprey from CA $260

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Our top choices for Osprey condo rentals

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 CA $249
CA $756 total
includes taxes & fees
Sep 18 - Sep 19
Turtle Nest

2. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,307 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is CA $209
CA $260 total
includes taxes & fees
Sep 17 - Sep 18
Captiva Beach Resort

3. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (680 reviews)
"Great stay!!"
United States
Genghis
The price is CA $256
CA $289 total
includes taxes & fees
Sep 20 - Sep 21
A Beach Retreat

4. 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 $149
CA $371 total
includes taxes & fees
Sep 17 - Sep 18
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

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

Jetties Pointe Cottage #6 - 408 “Casey Key”
Casey Key
10.0 out of 10, Exceptional, (19 reviews)
"Unique property, right on the beach . Great view from balcony Plan to visit again"
United States
Tonya
The price is CA $220
CA $514 total
includes taxes & fees
Sep 19 - Sep 20
Jetties Pointe Cottage #6 - 408 “Casey Key”

6. 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 CA $237
CA $495 total
includes taxes & fees
Sep 22 - Sep 23
Romantic Getaway Beach Club Siesta 202B by RVA

7. Private Gated Beach & Heated Pool: Modern Siesta Key Cottage at Beach Club on Crescent Beach

Private Gated Beach & Heated Pool: Modern Siesta Key Cottage at Beach Club on Crescent Beach
South Village
9.8 out of 10, Exceptional, (49 reviews)
"Great location for easy beach access. Clean property and great amenities."
United States
Jennifer G.
The price is CA $177
CA $758 total
includes taxes & fees
Sep 20 - Sep 21
Private Gated Beach & Heated Pool: Modern Siesta Key Cottage at Beach Club on Crescent Beach

8. 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 CA $277
CA $659 total
includes taxes & fees
Sep 17 - Sep 18
2BR Beach Style w Pool Beach Club Siesta 204C RVA

9. 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, (79 reviews)
"Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The stay was very good; the only thing I have to point out is that the Wi-Fi was very, very slow."
United States
Grisel E.
The price is CA $276
CA $656 total
includes taxes & fees
Sep 17 - Sep 18
Turquoise Water & Soft White Sand - The Beach Club at Siesta Key #104A by RVA

10. 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 CA $149
CA $465 total
includes taxes & fees
Sep 23 - Sep 24
Heart of Village: Dog-Friendly w/ Pool & Parking

11. 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)
"Good location, everything was clean. Enjoyed beach access. Will stay again."
United States
Pat G.
The price is CA $278
CA $617 total
includes taxes & fees
Sep 17 - Sep 18
Updated unit with easy beach access on Siesta Key

12. 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 $327
CA $643 total
includes taxes & fees
Sep 17 - Sep 18
Fully Renovated Beachside Getaway with Heated Pool – Walk to Restaurants

13. Location, location! Private Beach, Gulf Views from Balcony, Heated Pool, Siesta Sands with King Bed

Location, location! Private Beach, Gulf Views from Balcony, Heated Pool, Siesta Sands with King Bed
South Village
9.6 out of 10, Exceptional, (103 reviews)
"Nice condo, great view, perfect for us! "
United States
tracey h.
The price is CA $262
CA $1,024 total
includes taxes & fees
Sep 20 - Sep 21
Location, location! Private Beach, Gulf Views from Balcony, Heated Pool, Siesta Sands with King Bed

14. Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout
South Village
9.8 out of 10, Exceptional, (100 reviews)
"It was all great, really enjoyed our stay."
United States
Roger K.
The price is CA $353
CA $1,082 total
includes taxes & fees
Oct 8 - Oct 9
Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

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

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (35 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
The price is CA $215
CA $540 total
includes taxes & fees
Sep 18 - Sep 19
Jetties Pointe Cottage #5 - 408 “Casey Key”

16. 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 CA $221
CA $476 total
includes taxes & fees
Sep 20 - Sep 21
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

17. 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 CA $242
CA $506 total
includes taxes & fees
Sep 17 - Sep 18
1BR Pool-View Condo at The Beach Club on Siesta Key | Steps to the beach

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 CA $241
CA $504 total
includes taxes & fees
Sep 17 - Sep 18
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

19. 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, (144 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.
The price is CA $319
CA $1,066 total
includes taxes & fees
Sep 21 - Sep 22
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

20. 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 CA $215
CA $540 total
includes taxes & fees
Sep 23 - Sep 24
Jetties Pointe Cottage #2 - 408 “Casey Key”
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
2,026
Accommodation
3584 Condo Rentals
Lowest Price
CA $260
Highest Price
CA $2,731

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from CA $260 to CA $2,731 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 9.0. 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 3584 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 $260 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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