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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
9.8 out of 10, Exceptional, (18 reviews)
"Great place and location "
United States
Cathy
$519 nightly
The price is $558
May 10 - May 11
Total with taxes and fees
Chadwick Cove Resort & Marina

Lovely Condo! IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs

Lovely Condo! IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs
Bradenton
10.0 out of 10, Exceptional, (127 reviews)
"Great place to stay"
United States
Tawnee H.
$263 nightly
The price is $293
May 10 - May 11
Total with taxes and fees
Lovely Condo! IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs

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, (90 reviews)
"Location, amazing!!!"
United States
Krista M.
$590 nightly
The price is $658
May 13 - May 14
Total with taxes and fees
Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

Beautiful 2BR Condo · IMG 5 Mins · Anna Maria Island 15 Mins · Pools & Hot Tubs

Beautiful 2BR Condo · IMG 5 Mins · Anna Maria Island 15 Mins · Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (156 reviews)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
$258 nightly
The price is $288
May 10 - May 11
Total with taxes and fees
Beautiful 2BR Condo · IMG 5 Mins · Anna Maria Island 15 Mins · Pools & Hot Tubs

Shorewalk Palms Heaven 2BR Villa • 2 Pools & Heated Hot Tubs •Near IMG / Beaches

Shorewalk Palms Heaven 2BR Villa • 2 Pools & Heated Hot Tubs •Near IMG / Beaches
Bradenton
10.0 out of 10, Exceptional, (38 reviews)
"Great location between beaches and Sarasota activities. Nice space in a lovely community. "
United States
Sara
$224 nightly
The price is $250
May 11 - May 12
Total with taxes and fees
Shorewalk Palms Heaven 2BR Villa • 2 Pools & Heated Hot Tubs •Near IMG / Beaches

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (80 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
$323 nightly
The price is $361
May 13 - May 14
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Bradenton
9.8 out of 10, Exceptional, (140 reviews)
"Stayed at the same place before, lovely accommodation and location, and the host very welcoming and professional."
United States
John S.
$314 nightly
The price is $350
May 11 - May 12
Total with taxes and fees
*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (120 reviews)
"Perfect spot and host "
United States
Dee B.
$258 nightly
The price is $288
Jun 1 - Jun 2
Total with taxes and fees
Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

Waterfront Condo Walkable to Everything with Beach Access

Waterfront Condo Walkable to Everything with Beach Access
Manasota Key
9.6 out of 10, Exceptional, (50 reviews)
"Property managers were very helpful to work with and will still stay again despite a hiccup. "
United States
Jennifer J.
$432 nightly
The price is $446
May 10 - May 11
Total with taxes and fees
Waterfront Condo Walkable to Everything with Beach Access

Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN

Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN
Bradenton
10.0 out of 10, Exceptional, (12 reviews)
"The place is cozy and conveniently located to IMG Academy. New appliances and very clean. There are chairs for the beach which is helpful; Coquina Beach is 20 mins away."
United States
Jen
$303 nightly
The price is $337
May 11 - May 12
Total with taxes and fees
Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (82 reviews)
"Beautiful condo!! The owner was very responsive and attentive. We will definitely recommend this place to anyone!"
United States
Kay C.
$370 nightly
The price is $409
May 12 - May 13
Total with taxes and fees
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches

Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches
Bradenton
9.8 out of 10, Exceptional, (70 reviews)
"Excellent stay. Great place that was nice, clean and quiet. "
United States
David S.
$346 nightly
The price is $386
May 10 - May 11
Total with taxes and fees
Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (77 reviews)
"The pool was disgusting, dirt and debris on the bottom and top so that was disappointing, while watching TV and sleeping a person actually opened up our porch door then the main door and just walked in and said they had booked the same room and had keys, what kind of place does not keep track of that and I'm not sure what the person was thinking the TV was on and it was up a little so I know they heard it from the outside but to get back to that place for allowing that to happen. He's lucky I...
United States
Joseph
$272 nightly
The price is $304
May 13 - May 14
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA

*Casa Mia* Fabulous 2BR Condo w/2Pools, Mins to IMG/Beach/Anna Maria Isl

*Casa Mia* Fabulous 2BR Condo w/2Pools, Mins to IMG/Beach/Anna Maria Isl
Bradenton
9.8 out of 10, Exceptional, (130 reviews)
"Good location and clean unit"
United States
Ronald M.
$309 nightly
The price is $344
May 11 - May 12
Total with taxes and fees
*Casa Mia* Fabulous 2BR Condo w/2Pools, Mins to IMG/Beach/Anna Maria Isl

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (97 reviews)
"Beautiful sunset view. "
United States
Rhonda V.
$309 nightly
The price is $344
May 16 - May 17
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA

Turtle Nest

Turtle Nest
Sarasota
10.0 out of 10, Exceptional, (9 reviews)
"Great property and a great host! Easy and enjoyable stay. Will absolutely do again."
United States
Chris and Cecilia Z.
$484 nightly
The price is $540
May 11 - May 12
Total with taxes and fees
Turtle Nest

Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (87 reviews)
"Location #1. Clean #2"
United States
Eric C.
$340 nightly
The price is $379
May 11 - May 12
Total with taxes and fees
Silver Sands 1BR – Gulfside Comfort #255 by RVA

Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG

Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG
South Bradenton
$490 nightly
The price is $546
May 12 - May 13
Total with taxes and fees
Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (95 reviews)
"Great view, clean, beautiful!"
United States
Bethany
$328 nightly
The price is $366
May 13 - May 14
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village
Siesta Key Village
9.4 out of 10, Exceptional, (81 reviews)
"This condo has been nicely appointed and has everything you need for a beach vacation. It's also in the village near all shops and eateries. "
United States
Abi-Gayil G.
$515 nightly
The price is $574
May 10 - May 11
Total with taxes and fees
Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village
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
1,389
Accommodation
3627 Condo Rentals
Lowest Price
$250
Highest Price
$658

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $250 to $658 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 3627 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 $250 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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