Search and Rent Osprey Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (17 reviews)
"Great place and location "
United States
Cathy
$650 nightly
The price is $704
Mar 15 - Mar 16
Total with taxes and fees
Chadwick Cove Resort & Marina

Condo in Bayou Oaks

Riverside Oasis 1Bed/1Bath
9.2 out of 10, Wonderful, (46 reviews)
"Excellent place to stay"
United States
garry s.
$129 nightly
The price is $143
Mar 22 - Mar 23
Total with taxes and fees
Riverside Oasis 1Bed/1Bath
9.4 out of 10, Exceptional, (13 reviews)
"We loved the closeness to the bay, our backyard"
United States
Alec V.
$540 nightly
The price is $603
Apr 1 - Apr 2
Total with taxes and fees
Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock
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.
$349 nightly
The price is $389
Mar 15 - Mar 16
Total with taxes and fees
Silver Sands Serenity – Unit 234 by RVA
10.0 out of 10, Exceptional, (12 reviews)
"The host was great, everything we needed was already there. Great property, super clean, excellent location. "
United States
Ellen L.
$305 nightly
The price is $342
Apr 9 - Apr 10
Total with taxes and fees
Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN
9.8 out of 10, Exceptional, (151 reviews)
"Great location, clean, everything we needed for a low key beach vacation!"
United States
Stephanie H.
$296 nightly
The price is $332
Apr 4 - Apr 5
Total with taxes and fees
Cozy 2BR Condo ~ Heated Pools & Fast WiFi ~ Minutes to Anna Maria Island & IMG
9.8 out of 10, Exceptional, (117 reviews)
"Enjoyed our stay, we will return for future fun in AMI"
United States
Karen J.
$296 nightly
The price is $332
Apr 9 - Apr 10
Total with taxes and fees
Serene Waterfront Retreat ~ 2BR, Pools & Private Lanai ~ Near Anna Maria & IMG
9.8 out of 10, Exceptional, (136 reviews)
"The condo was cleaned and well maintained. "
United States
Scott Z.
$417 nightly
The price is $466
Mar 13 - Mar 14
Total with taxes and fees
*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
8.0 out of 10, Very Good, (12 reviews)
"Amazing property with direct beach access. "
United States
maria m.
$347 nightly
The price is $387
Mar 23 - Mar 24
Total with taxes and fees
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

Condo in Bradenton

Beautifully furnished condo
9.8 out of 10, Exceptional, (155 reviews)
"We would stay there again."
United States
Connie S.
$284 nightly
The price is $318
Mar 31 - Apr 1
Total with taxes and fees
Beautifully furnished condo
9.8 out of 10, Exceptional, (144 reviews)
"Great location, great property! "
United States
Chelsy K.
$365 nightly
The price is $402
Apr 7 - Apr 8
Total with taxes and fees
Beachfront Escape – Private Balcony, Gulf Views, No Street to Cross
8.8 out of 10, Excellent, (92 reviews)
"Gorgeous location, the beach was exceptional and the area was quiet and felt secluded. The condo was a bit shabby but clean and had everything we needed. "
United States
Jessie
$358 nightly
The price is $399
Mar 16 - Mar 17
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA
10.0 out of 10, Exceptional, (11 reviews)
"The location was perfect. The dock is awesome for fishing. The balcony is great for views."
United States
Adrienne W.
$677 nightly
The price is $755
Mar 12 - Mar 13
Total with taxes and fees
Pelican at Coastal Breeze | Stunning Water Views | Quiet Bayfront Balcony | Dock Access | Beach Gear
10.0 out of 10, Exceptional, (21 reviews)
"Will stay here again."
United States
Anonymous traveler
$532 nightly
The price is $595
Apr 1 - Apr 2
Total with taxes and fees
Turtle at Coastal Breeze | Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing
8.8 out of 10, Excellent, (24 reviews)
"Great location. We loved that it was an easy drive to lots of parks an other attractions. Great beach walks."
United States
Deb W.
$393 nightly
The price is $438
Mar 11 - Mar 12
Total with taxes and fees
1BR Beach Oasis – Silver Sands #258, Longboat Key by RVA
9.4 out of 10, Exceptional, (136 reviews)
"Great place. Easy check in and check out.Very cozy."
United States
Anonymous traveler
$335 nightly
The price is $375
Mar 11 - Mar 12
Total with taxes and fees
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
10.0 out of 10, Exceptional, (65 reviews)
"Great stay - great location for what we needed. Everything was as listed - host was very helpful. "
United States
Emily S.
$342 nightly
The price is $383
Apr 9 - Apr 10
Total with taxes and fees
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
7.8 out of 10, Good, (9 reviews)
"Great locale right on the beach "
United States
Carole
$429 nightly
The price is $478
Mar 30 - Mar 31
Total with taxes and fees
Beachfront Bliss on Longboat Key- Steps to the sand
10.0 out of 10, Exceptional, (32 reviews)
"This is a beautiful condo with all of the amenities you would want in a location that is close to stores, restaurants, etc. The host checked in with us to make sure we had everything we needed. We will definitely stay here in the future! This was a 10/10 stay!"
United States
Petula G.
$411 nightly
The price is $458
Mar 24 - Mar 25
Total with taxes and fees
Shorewalk Palms Heaven 2BR Villa • 2 Pools & Heated Hot Tubs •Near IMG / Beaches
9.2 out of 10, Wonderful, (61 reviews)
"Perfect stay for a quick Birthday trip. "
United States
melissa b.
$393 nightly
The price is $435
Mar 15 - Mar 16
Total with taxes and fees
3 Bedroom- Beachfront Condo with 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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Osprey Hotel Reviews

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,057
Accommodation
3715 Condo Rentals
Lowest Price
$143
Highest Price
$704

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $143 to $704 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 3715 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 $143 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.

Explore a world of travel with Expedia