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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Osprey condo rentals

Exterior

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (15 reviews)
"Great place and location "
United States
Cathy
The price is SAR 474
SAR 2,219 total
includes taxes & fees
18 Jan - 19 Jan
Chadwick Cove Resort & Marina
Interior

Condo in Manasota Key

3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf
9.6 out of 10, Exceptional, (60 reviews)
"Very good view"
United States
william t.
The price is SAR 1,043
SAR 2,000 total
includes taxes & fees
29 Jan - 30 Jan
3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf
Exterior

Condo in Siesta Key

Coastal Breeze Siesta - Turtle
2.0 star property
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 SAR 612
SAR 1,578 total
includes taxes & fees
18 Jan - 19 Jan
Coastal Breeze Siesta - Turtle
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, individually decorated

Condo in Casey Key

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

Condo in Sarasota

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

Condo in Sarasota

Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!
9.2 out of 10, Wonderful, (10 reviews)
"We loved the closeness to the bay, our backyard"
United States
Alec V.
Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!
Marina

Condo in Manasota Key

Bayfront Condo Walkable to Everything. Unit 2
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 SAR 563
SAR 1,496 total
includes taxes & fees
23 Jan - 24 Jan
Bayfront Condo Walkable to Everything. Unit 2
Terrace/patio

Condo in Venice Island

Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available
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 SAR 649
SAR 1,653 total
includes taxes & fees
30 Jan - 31 Jan
Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available
Property grounds

Condo in Bradenton

Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
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.
The price is SAR 570
SAR 1,478 total
includes taxes & fees
18 Jan - 19 Jan
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Terrace/patio

Condo in Sarasota

Turtle Nest
10.0 out of 10, Exceptional, (3 reviews)
"Highly recommend - we'll be back!"
United States
GK M.
Turtle Nest
Beach nearby

Condo in Siesta Key

Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool
9.0 out of 10, Wonderful, (21 reviews)
"Great stay. Great place."
United States
Jennifer h.
Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool
Outdoor pool, a heated pool

Condo in Whitfield Estates

Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
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 SAR 354
SAR 759 total
includes taxes & fees
19 Jan - 20 Jan
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
Interior

Condo in Longboat Key

Sunset and Beach view unit 402
9.8 out of 10, Exceptional, (15 reviews)
"Accommodation were outstanding with beautiful views of the gulf!"
United States
Mike C.
The price is SAR 563
SAR 1,364 total
includes taxes & fees
21 Jan - 22 Jan
Sunset and Beach view unit 402
Sun loungers, beach towels

Condo in Bradenton

Beautifully furnished condo
9.8 out of 10, Exceptional, (151 reviews)
"We would stay there again."
United States
Connie S.
The price is SAR 536
SAR 1,185 total
includes taxes & fees
31 Jan - 1 Feb
Beautifully furnished condo
Beach nearby

Condo in South Bradenton

*Charming 2bed 2 bath 6 mins from IMG*
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 SAR 611
SAR 1,540 total
includes taxes & fees
20 Jan - 21 Jan
*Charming 2bed 2 bath 6 mins from IMG*
Beach nearby

Condo in South Bradenton

Modern Coastal 2/2 condo w/pool 6 mins to IMG
9.8 out of 10, Exceptional, (28 reviews)
"Great place to stay !"
Canada
Teddy N.
The price is SAR 581
SAR 1,525 total
includes taxes & fees
20 Jan - 21 Jan
Modern Coastal 2/2 condo w/pool 6 mins to IMG
Beach nearby, beach umbrellas, beach towels

Condo in Longboat Key

Coastal Comfort - Beach Castle #23 by RVA
10.0 out of 10, Exceptional, (55 reviews)
"Amazing family vacation and loved the location!"
United States
Kaitlin M.
The price is SAR 1,260
SAR 2,277 total
includes taxes & fees
6 Feb - 7 Feb
Coastal Comfort - Beach Castle #23 by RVA
On the beach, sun loungers, beach towels

Condo in South Village

Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
2.0 star property
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 SAR 844
SAR 1,663 total
includes taxes & fees
17 Jan - 18 Jan
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
Beach nearby

Condo in Longboat Key

Best views of the beach from your balcony Unit 301
9.8 out of 10, Exceptional, (88 reviews)
"It was so great loved everything in the home"
United States
TERRY C.
The price is SAR 694
SAR 1,569 total
includes taxes & fees
23 Jan - 24 Jan
Best views of the beach from your balcony Unit 301
Property grounds

Condo in Bradenton

Elegant Waterfront Condo: Two Pools~Private Lanai~WiFi! Near IMG~AMI~Restaurants
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 SAR 398
SAR 1,181 total
includes taxes & fees
19 Jan - 20 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

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"The room was spacious and clean! Had a great view of the pool and a balcony! The property looks older but the rooms are remodeled nicely! Will for sure stay again. The staff was incredible helpful and friendly!"
Stephany 2-night trip
Posted 2 days ago
Golden Host Resort - Sarasota

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from SAR 759 to SAR 2,277 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 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 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.
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 kilometers 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 kilometers 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.