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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Osprey condo rentals

A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

1. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,303 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
$165 nightly
The price is $184
Sep 8 - Sep 9
Total with taxes and fees
Captiva Beach Resort
A covered patio with a sofa, a table, and potted plants.

2. 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
$488 nightly
The price is $544
Sep 8 - Sep 9
Total with taxes and fees
Turtle Nest
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

3. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (672 reviews)
"Lovely place on a family beach."
United States
Robert
$205 nightly
The price is $231
Sep 7 - Sep 8
Total with taxes and fees
A Beach Retreat
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

4. 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.
$429 nightly
The price is $478
Sep 7 - Sep 8
Total with taxes and fees
The Beach Club at Siesta Key #106A Resort by RVA
A beach with a building in the background during sunset.

5. 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.
$259 nightly
The price is $289
Sep 7 - Sep 8
Total with taxes and fees
Canalfront Siesta key entire King suite
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

6. 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.
$319 nightly
The price is $355
Sep 7 - Sep 8
Total with taxes and fees
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

7. 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.
$227 nightly
The price is $253
Sep 9 - Sep 10
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A beach path leading to the sea with grass on either side.

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

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (34 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
$348 nightly
The price is $387
Sep 13 - Sep 14
Total with taxes and fees
Jetties Pointe Cottage #5 - 408 “Casey Key”
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

9. 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
$425 nightly
The price is $473
Sep 7 - Sep 8
Total with taxes and fees
2BR Beach Style w Pool Beach Club Siesta 204C RVA
A beach with clear blue water and a sandy shore.

10. Beachfront Getaway in Siesta Key

Beachfront Getaway in Siesta Key
South Village
9.8 out of 10, Exceptional, (39 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.
$345 nightly
The price is $385
Sep 17 - Sep 18
Total with taxes and fees
Beachfront Getaway in Siesta Key
A beach with tall grasses and a sunset.

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
$404 nightly
The price is $450
Sep 8 - Sep 9
Total with taxes and fees
Renovated condo with easy beach access on Siesta
A beach with tall grasses and a sunset.

12. 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.
$345 nightly
The price is $385
Sep 7 - Sep 8
Total with taxes and fees
Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach
A beach with a clear sky and calm sea.

13. 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.
$336 nightly
The price is $354
Sep 9 - Sep 10
Total with taxes and fees
Heart of Village: Dog-Friendly w/ Pool & Parking
A beach with tall grasses and a sunset.

14. 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, (143 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.
$264 nightly
The price is $295
Sep 8 - Sep 9
Total with taxes and fees
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

15. Tropical Waters & Sunsets–Beach Club Siesta 106B RVA

Tropical Waters & Sunsets–Beach Club Siesta 106B RVA
South Village
8.4 out of 10, Very Good, (68 reviews)
"Easy walk to great beach"
United States
Carole A.
$396 nightly
The price is $442
Sep 7 - Sep 8
Total with taxes and fees
Tropical Waters & Sunsets–Beach Club Siesta 106B RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

16. 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
$324 nightly
The price is $361
Sep 7 - Sep 8
Total with taxes and fees
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.

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.
$325 nightly
The price is $362
Sep 7 - Sep 8
Total with taxes and fees
1BR Pool-View Condo at The Beach Club on Siesta Key | Steps to the beach
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

18. 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 traveler
$320 nightly
The price is $357
Sep 7 - Sep 8
Total with taxes and fees
Romantic Getaway Beach Club Siesta 202B by RVA
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.
$324 nightly
The price is $361
Sep 7 - Sep 8
Total with taxes and fees
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. 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, (76 reviews)
"Great short stay. Close walk to the beach! "
United States
Tera S.
$410 nightly
The price is $457
Sep 7 - Sep 8
Total with taxes and fees
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E 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 Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"We had a wonderful time here!! Close to a beautiful beach with amazing sunsets!! Their new pool was AMAZING with waterfalls and plenty of comfortable lounges and umbrellas! The front desk person learned it was our 30th wedding anniversary and changed our room to a better location. We also arrived really early and were prepared to be turned away, but we were welcomed and allowed early check in! It is walking distance to and amazing seafood restaurant, awesome pizza, a breakfast restaurant, ice cream and more!! Highly recommend and hope to make stays here a yearly thing!!"
Mark 4-night trip
Posted 3 hours ago
Tropical Beach Resorts

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,615
Accommodation
3588 Condo Rentals
Lowest Price
$184
Highest Price
$544

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $184 to $544 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 9.2. Venice Beach Villas comes highly recommended if you're traveling 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 3588 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 $184 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 favorite 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 7 miles 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 5 miles from the center 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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