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

Manatee at Coastal Breeze | Waterfront | Dock & Fishing | Turtle Beach | Siesta Key

Manatee at Coastal Breeze | Waterfront | Dock & Fishing | Turtle Beach | Siesta Key
Sarasota
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful location Perfect for what we wanted in a quick escape. "
United States
Antonio
Manatee at Coastal Breeze | Waterfront | Dock & Fishing | Turtle Beach | Siesta Key

Turtle Nest

Turtle Nest
Sarasota
10.0 out of 10, Exceptional, (11 reviews)
"Check was smooth and easy and location was GREAT!"
United States
Annie S.
$485 nightly
The price is $541
Aug 3 - Aug 4
Total with taxes and fees
Turtle Nest

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,290 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
$180 nightly
The price is $201
Aug 9 - Aug 10
Total with taxes and fees
Captiva Beach Resort

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (655 reviews)
"The beach is right there, very clean and nice place."
United States
Maryna
$205 nightly
The price is $231
Aug 2 - Aug 3
Total with taxes and fees
A Beach Retreat

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.
$280 nightly
The price is $312
Aug 2 - Aug 3
Total with taxes and fees
Heated Pool Apartment Near Siesta Key 1BR

Canalfront Siesta key entire King suite

Canalfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful stay nice secluded.but still close to all sites to see very relaxing you couldnt find more wonderful host Sue & Nandy beautiful experience "
United States
Brian B.
$259 nightly
The price is $289
Aug 11 - Aug 12
Total with taxes and fees
Canalfront Siesta key entire King suite

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)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
$328 nightly
The price is $365
Jul 31 - Aug 1
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

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, (88 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
$320 nightly
The price is $357
Jul 26 - Jul 27
Total with taxes and fees
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Jetties Pointe Cottage #5 - 408 “Casey Key”

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.8 out of 10, Exceptional, (31 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
$377 nightly
The price is $420
Aug 3 - Aug 4
Total with taxes and fees
Jetties Pointe Cottage #5 - 408 “Casey Key”

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
10.0 out of 10, Exceptional, (36 reviews)
"This is the cleanest house we have ever stayed in. Very well equipped. Just a few minutes' walk to the beach. It is located in a quiet area. I would definitely rent it again."
United States
Noraycis
$574 nightly
The price is $640
Jul 27 - Jul 28
Total with taxes and fees
Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!

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
$574 nightly
The price is $640
Aug 19 - Aug 20
Total with taxes and fees
Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

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, (140 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.
$324 nightly
The price is $361
Aug 17 - Aug 18
Total with taxes and fees
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

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
$434 nightly
The price is $484
Jul 26 - Jul 27
Total with taxes and fees
2BR Beach Style w Pool Beach Club Siesta 204C RVA

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, (95 reviews)
"Location, amazing!!!"
United States
Krista M.
Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

Siesta Key Condo: Beach, Pool & Village Fun!

Siesta Key Condo: Beach, Pool & Village Fun!
Siesta Key Village
9.2 out of 10, Wonderful, (15 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.
$387 nightly
The price is $411
Aug 2 - Aug 3
Total with taxes and fees
Siesta Key Condo: Beach, Pool & Village Fun!

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
$376 nightly
The price is $420
Aug 14 - Aug 15
Total with taxes and fees
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

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, (141 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.
$760 nightly
The price is $848
Jul 27 - Jul 28
Total with taxes and fees
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

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
$431 nightly
The price is $480
Jul 26 - Jul 27
Total with taxes and fees
Turquoise Water & Soft White Sand - The Beach Club at Siesta Key #104A by RVA

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.
Updated unit with easy beach access on Siesta Key

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)
"We enjoyed our stay, would stay again."
United States
Robert
$326 nightly
The price is $363
Jul 27 - Jul 28
Total with taxes and fees
Relax & Unwind – 1BR Beach Club Siesta Key 110D 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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Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from to 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 . 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 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 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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