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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Osprey condo rentals

Exterior

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
$503 nightly
The price is $540
Jan 27 - Jan 28
Total with taxes and fees
Chadwick Cove Resort & Marina
Beach nearby

New! Renovated Coastal 2/2, 6 mins to IMG

New! Renovated Coastal 2/2, 6 mins to IMG
South Bradenton
9.8 out of 10, Exceptional, (18 reviews)
"Accommodating for family group, quick drive to the beach."
United States
Ginger B.
$356 nightly
The price is $393
Jan 21 - Jan 22
Total with taxes and fees
New! Renovated Coastal 2/2, 6 mins to IMG
Fridge, microwave, oven, stovetop

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

*Modern 2/2 condo w/pool 6 mins to IMG*
South Bradenton
9.8 out of 10, Exceptional, (27 reviews)
"Great place. My family had a great time."
United States
AZAAM R.
$355 nightly
The price is $391
Jan 21 - Jan 22
Total with taxes and fees
*Modern 2/2 condo w/pool 6 mins to IMG*
TV

Casa Azul 2Bed/1Bath

Casa Azul 2Bed/1Bath
Bayou Oaks
9.6 out of 10, Exceptional, (70 reviews)
"We enjoyed our stay. Comfortable, neat and tidy. Everything we needed."
United States
Diana C.
Casa Azul 2Bed/1Bath
Beach

Upscale 2/2 Key West style condo 6 mins from IMG

Upscale 2/2 Key West style condo 6 mins from IMG
South Bradenton
10.0 out of 10, Exceptional, (23 reviews)
"Great location, attentive host, great stay"
United States
JUDY T.
$356 nightly
The price is $393
Jan 21 - Jan 22
Total with taxes and fees
Upscale 2/2 Key West style condo 6 mins from IMG
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, individually decorated

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
$184 nightly
The price is $208
Jan 21 - Jan 22
Total with taxes and fees
A Beach Retreat
Beach nearby

*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.
$356 nightly
The price is $392
Jan 21 - Jan 22
Total with taxes and fees
*Charming 2bed 2 bath 6 mins from IMG*
Terrace/patio

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.
$380 nightly
The price is $424
Jan 30 - Jan 31
Total with taxes and fees
Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available
Beach nearby

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.
$356 nightly
The price is $393
Jan 21 - Jan 22
Total with taxes and fees
Modern Coastal 2/2 condo w/pool 6 mins to IMG
Beach

*Farmhouse 2/2 Renovated Condo 6 mins from IMG*

*Farmhouse 2/2 Renovated Condo 6 mins from IMG*
South Bradenton
9.8 out of 10, Exceptional, (27 reviews)
"This was the perfect place to stay for an IMG baseball tournament. Very close to the facility as described. This condo unit was modern and clean. An overall excellent place to stay."
United States
Lassier
$337 nightly
The price is $372
Jan 21 - Jan 22
Total with taxes and fees
*Farmhouse 2/2 Renovated Condo 6 mins from IMG*
Marina

Bayfront Condo Walkable to Everything. Unit 2

Bayfront Condo Walkable to Everything. Unit 2
Manasota Key
9.6 out of 10, Exceptional, (50 reviews)
"We stayed in the 3 BR unit the month before and came back ...love this place!"
United States
Jo Ann K.
$324 nightly
The price is $358
Jan 23 - Jan 24
Total with taxes and fees
Bayfront Condo Walkable to Everything. Unit 2
Outdoor pool, a 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.
$175 nightly
The price is $205
Jan 21 - Jan 22
Total with taxes and fees
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,190 reviews)
"Excellent place and location, "
United States
Richard
$223 nightly
The price is $250
Jan 21 - Jan 22
Total with taxes and fees
Captiva Beach Resort
On the beach

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (73 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
$259 nightly
The price is $289
Jan 21 - Jan 22
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
Interior

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.
$332 nightly
The price is $366
Jan 21 - Jan 22
Total with taxes and fees
Sunset and Beach view unit 402
Beach

Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG

Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG
Bradenton
9.4 out of 10, Exceptional, (13 reviews)
"The location was great for traveling to events at the convention center. Lots of food options nearby. The property was clean. Check-in was simple. The host responded quickly to all of our communication and she was very nice to accommodate all of our requests. "
United States
Philippe G.
$267 nightly
The price is $298
Jan 21 - Jan 22
Total with taxes and fees
Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG
On the beach, beach umbrellas

Silver Sands Serenity – Unit 234 by RVA

Silver Sands Serenity – Unit 234 by RVA
Longboat Key
9.4 out of 10, Exceptional, (30 reviews)
"Love this place and staff. Will book again. Everything is so easy!"
United States
Emily
$294 nightly
The price is $328
Jan 24 - Jan 25
Total with taxes and fees
Silver Sands Serenity – Unit 234 by RVA
Terrace/patio

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (56 reviews)
"A cute and cozy place to stay. Located in a good spot. Close to every thing we wanted to do. "
United States
Beth H.
$171 nightly
The price is $191
Feb 8 - Feb 9
Total with taxes and fees
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Beach nearby

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.
$376 nightly
The price is $414
Jan 23 - Jan 24
Total with taxes and fees
Best views of the beach from your balcony Unit 301
Interior

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.
$481 nightly
The price is $532
Jan 24 - Jan 25
Total with taxes and fees
3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf
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 pool area was clean and poo was warm it was pretty cold during our visit so we may have just dipped some toes in. But it was great"
Kelsey 1-night trip
Posted 1 day ago
Golden Host Resort - Sarasota

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
2,473
Accommodation
3714 Condo Rentals
Lowest Price
$191
Highest Price
$540

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $191 to $540 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 9.5. 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.
What are the best cheap condos in Osprey?
With condos starting from $191 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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