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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Osprey condo rentals

Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
$503 nightly
The price is $539
May 28 - May 29
Total with taxes and fees
Chadwick Cove Resort & Marina
Outdoor pool, pool umbrellas, sun loungers

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"Every room is very well equipped, I had to communicate with the host for some issues and it was really easy and helpful, I would recommend this place!"
United States
Liz
$311 nightly
The price is $351
Jun 2 - Jun 3
Total with taxes and fees
Cedar Run Resort - Roam Hospitality
Sun loungers, beach towels

Waterfront Siesta key entire King suite

Waterfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (10 reviews)
$245 nightly
The price is $273
May 28 - May 29
Total with taxes and fees
Waterfront Siesta key entire King suite
Exterior

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.
$423 nightly
The price is $436
May 28 - May 29
Total with taxes and fees
Waterfront Condo Walkable to Everything with Beach Access
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)
" Great location, office staff are very pleasant, room was very spacious with everything you need"
United States
GLENNA M.
$315 nightly
The price is $351
May 28 - May 29
Total with taxes and fees
Silver Sands Serenity – Unit 234 by RVA
Beach nearby, beach towels

2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches

2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches
Bradenton
9.8 out of 10, Exceptional, (122 reviews)
"Perfect spot and host "
United States
Dee B.
$274 nightly
The price is $306
Jun 1 - Jun 2
Total with taxes and fees
2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches
On the beach, beach umbrellas

Oceanfront 1BR – Silver Sands #257 by RVA

Oceanfront 1BR – Silver Sands #257 by RVA
Longboat Key
8.8 out of 10, Excellent, (48 reviews)
"Blown away at location and amenities! Spent 20 yrs renting on AMI, no more......this is what AMI used to be. Laid back, family oriented. Brittany checked us in and was soo very friendly. Room was great, rented for myself, spouse, and 2 adult children and we had plenty of room. Only thing that was disconcerting was the adjoining room.......we heard EVERYTHING coming from under the door which connects to the bedrooms. We will book again, but stuff towels under that door to help with the noise. "
United States
Kelly
$368 nightly
The price is $410
Jun 3 - Jun 4
Total with taxes and fees
Oceanfront 1BR – Silver Sands #257 by RVA
Beach nearby, sun loungers, beach towels

Upscale 2BR Condo w/ Lanai · Two Pools & Hot Tubs · IMG Academy · Gulf Beaches

Upscale 2BR Condo w/ Lanai · Two Pools & Hot Tubs · IMG Academy · Gulf Beaches
Bradenton
10.0 out of 10, Exceptional, (129 reviews)
"Lovely spot. Clean and roomy. Host was easy to contact and accommodating. "
United States
April R.
$272 nightly
The price is $304
May 29 - May 30
Total with taxes and fees
Upscale 2BR Condo w/ Lanai · Two Pools & Hot Tubs · IMG Academy · Gulf Beaches
On the beach

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (81 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
$332 nightly
The price is $370
May 28 - May 29
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA
Lobby

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (480 reviews)
"Clean room, staff was excellent. Close to downtown area and beach, all within walking distance. "
Canada
John
$201 nightly
The price is $228
Jun 5 - Jun 6
Total with taxes and fees
Venice Beach Villas
Beach

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

Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG
Bradenton
9.6 out of 10, Exceptional, (28 reviews)
"Perfect for our weekend getaway Full kitchen / easy for cooking in Pool was nice for us"
United States
Carolyn
$187 nightly
The price is $208
May 28 - May 29
Total with taxes and fees
Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG
On the beach

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (78 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
$277 nightly
The price is $309
May 28 - May 29
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
Property grounds

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.
$343 nightly
The price is $383
May 28 - May 29
Total with taxes and fees
Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches
Interior

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, (13 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
$305 nightly
The price is $340
Jun 1 - Jun 2
Total with taxes and fees
Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN
Beach nearby

Coastal Comfort – Beach Castle #26 by RVA

Coastal Comfort – Beach Castle #26 by RVA
Longboat Key
9.4 out of 10, Exceptional, (45 reviews)
"Easy check-in and out. The pool, hot tub and beach are great features. The unit is small, but had everything we needed. The only complaints we had were that the bed was very hard and not comfortable, and there is very limited parking. We had a nice stay and enjoyed LBK. "
United States
Laura K.
$296 nightly
The price is $330
May 28 - May 29
Total with taxes and fees
Coastal Comfort – Beach Castle #26 by RVA
On the beach, beach umbrellas

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (80 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
$316 nightly
The price is $353
May 28 - May 29
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
Sun loungers, beach towels

2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches

2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches
Bradenton
9.8 out of 10, Exceptional, (156 reviews)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
$286 nightly
The price is $319
Jun 6 - Jun 7
Total with taxes and fees
2BR Corner Condo w/ Lanai · Dual Pools & Hot Tubs · IMG Academy · Gulf Beaches
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, (90 reviews)
"Everything was great "
United States
kirt v.
$377 nightly
The price is $415
Jun 6 - Jun 7
Total with taxes and fees
Best views of the beach from your balcony Unit 301
On the beach, beach umbrellas

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
$333 nightly
The price is $371
May 28 - May 29
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA
Sun loungers, beach towels

Shorewalk Sunny Bella Rosa • 2BR Villa • 2 Pools & Hot Tubs • Near IMG / Beaches

Shorewalk Sunny Bella Rosa • 2BR Villa • 2 Pools & Hot Tubs • Near IMG / Beaches
Bradenton
9.8 out of 10, Exceptional, (95 reviews)
"Very nice accommodations! I would suggest putting a shelf or niche in the master shower! There is only a soap dish with no where to sit shampoo, body wash etc!! Thank you for your kindness!! "
United States
Kimberly
$279 nightly
The price is $311
Jun 7 - Jun 8
Total with taxes and fees
Shorewalk Sunny Bella Rosa • 2BR Villa • 2 Pools & Hot Tubs • Near IMG / Beaches
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

Siesta Key Palms Resort

Siesta Key Palms Resort

10/10 Excellent
"Overall, excellent hotel."
Vanna 1-night trip
Posted less than an hour ago
Siesta Key Palms Resort

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,651
Accommodation
3628 Condo Rentals
Lowest Price
$208
Highest Price
$539

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $208 to $539 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 3628 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 $208 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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