Search Condos in Osprey

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Osprey condo rentals

Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,195 reviews)
"Excellent place and location, "
United States
Richard
The price is ￥33,725
￥40,734 total
includes taxes & fees
Feb 4 - Feb 5
Captiva Beach Resort
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, (593 reviews)
"The location is ideal, rooms are nice and the owners are extremely accommodating. "
United States
Catherine
A Beach Retreat
1 bedroom, desk, iron/ironing board, WiFi

Riverside Oasis 1Bed/1Bath

Riverside Oasis 1Bed/1Bath
Bayou Oaks
9.2 out of 10, Wonderful, (43 reviews)
"Excellent place to stay"
United States
garry s.
The price is ￥11,454
￥22,160 total
includes taxes & fees
Feb 8 - Feb 9
Riverside Oasis 1Bed/1Bath
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.
The price is ￥18,221
￥35,799 total
includes taxes & fees
Feb 4 - Feb 5
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
1 bedroom, desk, iron/ironing board, WiFi

The Sapphire Suite 1Bed/1Bath

The Sapphire Suite 1Bed/1Bath
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (90 reviews)
"We loved our stay here, it was a perfect location with lots to do within even walking distance! "
United States
Austin S.
The price is ￥15,014
￥26,183 total
includes taxes & fees
Mar 2 - Mar 3
The Sapphire Suite 1Bed/1Bath
Sun loungers, beach towels

5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..

5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..
Sarasota
9.6 out of 10, Exceptional, (27 reviews)
"Excellent location and really nice atmosphere"
United States
Eduardo V.
The price is ￥21,669
￥67,917 total
includes taxes & fees
Feb 28 - Mar 1
5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..
Beach towels

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.
The price is ￥21,771
￥64,412 total
includes taxes & fees
Feb 28 - Mar 1
5 minutes drive to nr Siesta Key 1/1 Large condo. The pool heated
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (16 reviews)
"Great place and location "
United States
Cathy
The price is ￥27,318
￥100,576 total
includes taxes & fees
Feb 16 - Feb 17
Chadwick Cove Resort & Marina
Sun loungers

*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, (135 reviews)
"This is our second time staying here. This such a great location. We are always pleased with the layout and easy access to anywhere in the area. "
United States
Nancy D.
The price is ￥27,214
￥62,243 total
includes taxes & fees
Feb 18 - Feb 19
*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Property grounds

Stunning Waterfront Condo: Heated Pools~Lanai~WiFi! Near IMG~Beaches~Restaurants

Stunning Waterfront Condo: Heated Pools~Lanai~WiFi! Near IMG~Beaches~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 ￥17,845
￥51,191 total
includes taxes & fees
Feb 7 - Feb 8
Stunning Waterfront Condo: Heated Pools~Lanai~WiFi! Near IMG~Beaches~Restaurants
On the beach, sun loungers, beach towels

3 Bedroom-Beach Front Condo w/ Beautiful Views of the Gulf

3 Bedroom-Beach Front Condo w/ Beautiful Views of the Gulf
Manasota Key
9.6 out of 10, Exceptional, (57 reviews)
"Very clean. Great view. Only issue was no elevator but understand. Highly recommend "
United States
Mark R.
The price is ￥30,646
￥66,982 total
includes taxes & fees
Feb 5 - Feb 6
3 Bedroom-Beach Front Condo w/ Beautiful Views of the Gulf
On the beach

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (76 reviews)
"Perfect for our family."
United States
Kayla c.
The price is ￥20,014
￥51,225 total
includes taxes & fees
Feb 4 - Feb 5
Drift & Dune – Longboat Beachfront #101 RVA
TV

Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS

Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS
Sarasota
9.4 out of 10, Exceptional, (47 reviews)
"This is our second year staying at the villas i had a great time unit was cleaned ,pool was great,wahing machine worked good cant wait till next year"
United States
Edelmiro R.
The price is ￥23,171
￥48,245 total
includes taxes & fees
Feb 5 - Feb 6
Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS
Interior

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

3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf
Manasota Key
9.2 out of 10, Wonderful, (60 reviews)
"This rental is so comfortable and beautiful. You can tell that it's freshly remodeled everything is new and in perfect condition. Unfortunately many things in the area are still in bad shape from last year's hurricanes but this condo is located on a great shelling beach with beautiful sunsets. And we found lots of shark teeth!"
United States
Becky D.
The price is ￥30,646
￥66,982 total
includes taxes & fees
Feb 4 - Feb 5
3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf
Beach nearby

POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES
South Village
9.6 out of 10, Exceptional, (43 reviews)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
The price is ￥26,158
￥51,208 total
includes taxes & fees
Feb 9 - Feb 10
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES
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.
The price is ￥33,123
￥73,553 total
includes taxes & fees
Feb 4 - Feb 5
*Charming 2bed 2 bath 6 mins from IMG*
Beach

Solitude Suite Studio-Siesta Key-Waterfront Resort

Solitude Suite Studio-Siesta Key-Waterfront Resort
Siesta Key
8.0 out of 10, Very Good, (10 reviews)
"Check in was not smooth, I don’t believe I ever received an email detailing the check in process. We did get a text the morning of so we had contact info, but the text did not include check in information. When we arrived we had a hard time getting a hold of our contact. Internet also went out at one point and the contact was not very responsive. The bed was very uncomfortable, the blankets were very thin and given that it was cold when we were there it made it all the more uncomfortable....
United States
TAIYLOR
The price is ￥20,431
￥46,124 total
includes taxes & fees
Feb 4 - Feb 5
Solitude Suite Studio-Siesta Key-Waterfront Resort
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.
The price is ￥33,432
￥74,795 total
includes taxes & fees
Feb 4 - Feb 5
New! Renovated Coastal 2/2, 6 mins to IMG
Sun loungers

*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, (122 reviews)
"We absolutely loved our stay! Such clean and relaxing atmosphere. "
United States
Stephen
The price is ￥30,956
￥66,788 total
includes taxes & fees
Feb 27 - Feb 28
*Casa Mia* Fabulous 2BR Condo w/2Pools, Mins to IMG/Beach/Anna Maria Isl
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.
The price is ￥31,885
￥72,800 total
includes taxes & fees
Feb 4 - Feb 5
Modern Coastal 2/2 condo w/pool 6 mins to IMG
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"Nice modern room. Nice pool . Good food at lobby bar "
Gregory 5-night trip
Posted 1 day ago
Casey Key Resorts - Mainland

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
2,616
Accommodation
3714 Condo Rentals
Lowest Price
￥22,160
Highest Price
￥100,576

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from ￥22,160 to ￥100,576 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 9.4. 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 ￥22,160 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 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.
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.