Search and Rent Osprey Condos

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Our top choices for Osprey condo rentals

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
$508 nightly
The price is $545
Jan 7 - Jan 8, 2026
Total with taxes and fees
Chadwick Cove Resort & Marina
9.6 out of 10, Exceptional, (4)
"Great stay! "
United States
Athan K.
$252 nightly
The price is $281
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cozy 2-Bedroom Condo in Prime Siesta Key Location
10.0 out of 10, Exceptional, (119)
"We enjoyed our stay. Host is nice and respond quickly. "
Canada
Sonia S.
$298 nightly
The price is $333
Jan 3 - Jan 4, 2026
Total with taxes and fees
Lovely Waterfront Condo: Two Pools~Private Lanai~Fast WiFi! Near IMG~AMI~Beaches

Condo in Bayou Oaks

Casa Azul 2Bed/1Bath
9.6 out of 10, Exceptional, (69)
"We enjoyed our stay. Comfortable, neat and tidy. Everything we needed."
United States
Diana C.
Casa Azul 2Bed/1Bath

Condo in Whitfield Estates

The Getaway at the Marina
9.0 out of 10, Wonderful, (6)
"The property was as advertised. Clean with everything we needed for our stay. Owner was very responsive when I had a question. Front desk people were great and very helpful."
United States
Mary
$204 nightly
The price is $228
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Getaway at the Marina

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (580)
"Great location, recent updates"
United States
Michael
$184 nightly
The price is $208
Jan 4 - Jan 5, 2026
Total with taxes and fees
A Beach Retreat
9.8 out of 10, Exceptional, (39)
"Perfect for 2 adults and 2 kids. The house was very clean and all the extras in the kitchen were nice. Also, beach essentials are onsite so no need to bring much. Found lots of sharks teeth too! "
United States
Koren L.
$332 nightly
The price is $368
Jan 14 - Jan 15, 2026
Total with taxes and fees
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock

Condo in Indian Beach Sapphire Shores

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
9.8 out of 10, Exceptional, (55)
"A cute and cozy place to stay. Located in a good spot. Close to every thing we wanted to do. "
United States
Beth H.
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
9.4 out of 10, Exceptional, (47)
"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.
$220 nightly
The price is $246
Jan 4 - Jan 5, 2026
Total with taxes and fees
Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS
9.6 out of 10, Exceptional, (44)
"The location of the property could not have been better. A very short walk to the quietest beach on Siesta Key. The manager was very attentive when we called with a minor issue and had it resolved quickly. The property could use a pretty thorough cleaning of the baseboards and other nooks and crannies but overall it was pretty clean. We would stay again."
United States
Mel S.
$214 nightly
The price is $238
Jan 1 - Jan 2, 2026
Total with taxes and fees
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3
9.8 out of 10, Exceptional, (60)
"It was clean, comfy and ideal locarion. Close to beaches AMI and the pool was great. "
United States
Marge G.
$342 nightly
The price is $382
Jan 17 - Jan 18, 2026
Total with taxes and fees
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
9.8 out of 10, Exceptional, (18)
"Accommodating for family group, quick drive to the beach."
United States
Ginger B.
$404 nightly
The price is $445
Dec 30 - Dec 31
Total with taxes and fees
New! Renovated Coastal 2/2, 6 mins to IMG
9.6 out of 10, Exceptional, (41)
"Loved the pool and view!"
United States
Victoria P.
$220 nightly
The price is $246
Jan 4 - Jan 5, 2026
Total with taxes and fees
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

Condo in Bradenton

Beautifully furnished condo
9.8 out of 10, Exceptional, (149)
"Beautiful property and quiet. "
United States
Sandy K.
$254 nightly
The price is $282
Jan 5 - Jan 6, 2026
Total with taxes and fees
Beautifully furnished condo
8.2 out of 10, Very Good, (73)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
$255 nightly
The price is $285
Jan 9 - Jan 10, 2026
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
9.6 out of 10, Exceptional, (21)
"Cool place. Everything just as mentioned. Kids had a blast at pool and place was super clean"
United States
Jason G.
$380 nightly
The price is $418
Dec 30 - Dec 31
Total with taxes and fees
*Charming 2bed 2 bath 6 mins from IMG*
9.2 out of 10, Wonderful, (10)
"We loved the closeness to the bay, our backyard"
United States
Alec V.
$389 nightly
The price is $436
Jan 18 - Jan 19, 2026
Total with taxes and fees
Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!
9.6 out of 10, Exceptional, (31)
"The condo itself had everything we needed the covered out door balcony was perfect for relaxing with a drink before dinner with out having to be concerned with the sun or rain "
Canada
Joseph D C.
$630 nightly
The price is $703
Jan 3 - Jan 4, 2026
Total with taxes and fees
Newly Renovated Jamaica Royale Unit, Heated Pools
10.0 out of 10, Exceptional, (23)
"Great location, attentive host, great stay"
United States
JUDY T.
$417 nightly
The price is $460
Dec 30 - Dec 31
Total with taxes and fees
Upscale 2/2 Key West style condo 6 mins from IMG
9.8 out of 10, Exceptional, (149)
"Great location, clean, everything we needed for a low key beach vacation!"
United States
Stephanie H.
$302 nightly
The price is $337
Jan 2 - Jan 3, 2026
Total with taxes and fees
Beautiful 2BR Condo: Heated Pools~Fast WiFi. Near IMG~Beaches~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

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,349
Accommodation
3714 Condo Rentals
Lowest Price
$208
Highest Price
$703

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $208 to $703 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 $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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