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Our top choices for Osprey condo rentals

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (15 reviews)
"Great place and location "
United States
Cathy
The price is €508
includes taxes & fees
18 Jan - 19 Jan
Chadwick Cove Resort & Marina

3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf

3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf
Manasota Key
9.6 out of 10, Exceptional, (60 reviews)
"Very good view"
United States
william t.
The price is €458
includes taxes & fees
24 Jan - 25 Jan
3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf

Coastal Breeze Siesta - Turtle

Coastal Breeze Siesta - Turtle
2.0 star property
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"Great little place to stay and enjoy the nearby beaches and restaurants! The communication was on point. We will be back "
United States
Jacob
The price is €361
includes taxes & fees
18 Jan - 19 Jan
Coastal Breeze Siesta - Turtle

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (586 reviews)
"Room was nice & staff was friendly. "
United States
Paula
A Beach Retreat

5 minutes drive to nr Siesta Key 1/1 Large condo. The pool heated

5 minutes drive to nr Siesta Key 1/1 Large condo. The pool heated
Sarasota
10.0 out of 10, Exceptional, (13 reviews)
"The place was exactly what I needed: Clean, open, and easy access to our destinations. Communication with the owner was great. I'd do it again!"
United States
ken s.
5 minutes drive to nr Siesta Key 1/1 Large condo. The pool heated

Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!

Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!
Sarasota
9.2 out of 10, Wonderful, (10 reviews)
"We loved the closeness to the bay, our backyard"
United States
Alec V.
The price is €376
includes taxes & fees
18 Jan - 19 Jan
Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!

Bayfront Condo Walkable to Everything. Unit 2

Bayfront Condo Walkable to Everything. Unit 2
Manasota Key
9.6 out of 10, Exceptional, (49 reviews)
"We stayed in the 3 BR unit the month before and came back ...love this place!"
United States
Jo Ann K.
The price is €351
includes taxes & fees
23 Jan - 24 Jan
Bayfront Condo Walkable to Everything. Unit 2

Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available

Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available
Venice Island
9.8 out of 10, Exceptional, (105 reviews)
"Absolutely wonderful rental home, very clean and comfortable in a fabulous location close to town and the beaches. One of my best stays in Venice and would highly recommend!"
United States
Bonnie S.
The price is €385
includes taxes & fees
30 Jan - 31 Jan
Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available

Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Bradenton
9.8 out of 10, Exceptional, (60 reviews)
"It was clean, comfy and ideal locarion. Close to beaches AMI and the pool was great. "
United States
Marge G.
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Turtle Nest

Turtle Nest
Sarasota
10.0 out of 10, Exceptional, (3 reviews)
"Highly recommend - we'll be back!"
United States
GK M.
The price is €575
includes taxes & fees
29 Jan - 30 Jan
Turtle Nest

Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool

Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool
Siesta Key
9.0 out of 10, Wonderful, (21 reviews)
"Great stay. Great place."
United States
Jennifer h.
The price is €306
includes taxes & fees
20 Jan - 21 Jan
Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool

Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!

Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
Whitfield Estates
9.2 out of 10, Wonderful, (49 reviews)
"Great place and great location! We really enjoyed our stay!"
United States
Meghan I.
The price is €178
includes taxes & fees
29 Jan - 30 Jan
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!

Sunset and Beach view unit 402

Sunset and Beach view unit 402
Longboat Key
9.8 out of 10, Exceptional, (15 reviews)
"Accommodation were outstanding with beautiful views of the gulf!"
United States
Mike C.
The price is €318
includes taxes & fees
21 Jan - 22 Jan
Sunset and Beach view unit 402

Beautifully furnished condo

Beautifully furnished condo
Bradenton
9.8 out of 10, Exceptional, (151 reviews)
"We would stay there again."
United States
Connie S.
Beautifully furnished condo

*Charming 2bed 2 bath 6 mins from IMG*

*Charming 2bed 2 bath 6 mins from IMG*
South Bradenton
9.6 out of 10, Exceptional, (21 reviews)
"Cool place. Everything just as mentioned. Kids had a blast at pool and place was super clean"
United States
Jason G.
The price is €379
includes taxes & fees
19 Jan - 20 Jan
*Charming 2bed 2 bath 6 mins from IMG*

Modern Coastal 2/2 condo w/pool 6 mins to IMG

Modern Coastal 2/2 condo w/pool 6 mins to IMG
South Bradenton
9.8 out of 10, Exceptional, (28 reviews)
"Great place to stay !"
Canada
Teddy N.
The price is €362
includes taxes & fees
20 Jan - 21 Jan
Modern Coastal 2/2 condo w/pool 6 mins to IMG

Coastal Comfort - Beach Castle #23 by RVA

Coastal Comfort - Beach Castle #23 by RVA
Longboat Key
10.0 out of 10, Exceptional, (55 reviews)
"Amazing family vacation and loved the location!"
United States
Kaitlin M.
The price is €532
includes taxes & fees
6 Feb - 7 Feb
Coastal Comfort - Beach Castle #23 by RVA

Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!

Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
2.0 star property
South Village
10.0 out of 10, Exceptional, (6 reviews)
"Great time and great accommodations. Phyllis was great to work with and will rent again."
United States
Gabe L.
The price is €451
includes taxes & fees
19 Jan - 20 Jan
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!

Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (88 reviews)
"It was so great loved everything in the home"
United States
TERRY C.
The price is €368
includes taxes & fees
23 Jan - 24 Jan
Best views of the beach from your balcony Unit 301

Elegant Waterfront Condo: Two Pools~Private Lanai~WiFi! Near IMG~AMI~Restaurants

Elegant Waterfront Condo: Two Pools~Private Lanai~WiFi! Near IMG~AMI~Restaurants
Bradenton
9.8 out of 10, Exceptional, (115 reviews)
"Enjoyed our stay, we will return for future fun in AMI"
United States
Karen J.
The price is €279
includes taxes & fees
29 Jan - 30 Jan
Elegant Waterfront Condo: Two Pools~Private Lanai~WiFi! Near IMG~AMI~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
1,369
Accommodation
3714 Condo Rentals
Lowest Price
€178
Highest Price
€575

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from €178 to €575 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 9.6. 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 holiday dates and then pick from 3714 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 €178 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 accommodation 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 travellers alike.