A marina with docked boats, a wooden bridge, and a building with a red roof.

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Osprey condo rentals

Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
$545 nightly
The price is $586
Jul 7 - Jul 8
Total with taxes and fees
Chadwick Cove Resort & Marina
Beach nearby, beach towels

Waterfront Condo w/ Lanai · Pools & Hot Tubs · IMG Academy · Anna Maria Island

Waterfront Condo w/ Lanai · Pools & Hot Tubs · IMG Academy · Anna Maria Island
Bradenton
9.8 out of 10, Exceptional, (121 reviews)
"We loved the property, large pool & access to activities. "
United States
Mary Beth M.
$297 nightly
The price is $331
Jul 31 - Aug 1
Total with taxes and fees
Waterfront Condo w/ Lanai · Pools & Hot Tubs · IMG Academy · Anna Maria Island
Outdoor pool, pool umbrellas, sun loungers

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.0 out of 10, Wonderful, (6 reviews)
"I would stay again, very accommodating"
United States
Deliondra
$554 nightly
The price is $626
Jul 1 - Jul 2
Total with taxes and fees
Cedar Run Resort - Roam Hospitality
Beach nearby, sun loungers, beach towels, snorkeling

Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock

Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock
Sarasota
9.6 out of 10, Exceptional, (16 reviews)
"the place was great and the host was very responsive to out requests."
United States
David R.
$510 nightly
The price is $569
Jul 2 - Jul 3
Total with taxes and fees
Dolphin at Coastal Breeze | Quiet and Cozy Retreat, Walk to Turtle Beach, Bayfront Patio, Boat Dock
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, (14 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
Jul 1 - Jul 2
Total with taxes and fees
Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN
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
$317 nightly
The price is $353
Jul 12 - Jul 13
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
Sun loungers, beach towels

Beautiful Corner Condo · Resort Pools/Hot Tubs · IMG Academy · Anna Maria Island

Beautiful Corner Condo · Resort Pools/Hot Tubs · IMG Academy · Anna Maria Island
Bradenton
9.8 out of 10, Exceptional, (159 reviews)
"It was a very clean apartment and the host answered all my questions quickly! Very nice experience!!"
United States
Michael P.
$278 nightly
The price is $309
Jul 2 - Jul 3
Total with taxes and fees
Beautiful Corner Condo · Resort Pools/Hot Tubs · IMG Academy · Anna Maria Island
Outdoor pool, a heated pool

Unlimited Golf with membership transfer- Lakewood National

Unlimited Golf with membership transfer- Lakewood National
Bradenton
10.0 out of 10, Exceptional, (23 reviews)
"Zoe was a great host and quick to answer any questions."
United States
John K.
Unlimited Golf with membership transfer- Lakewood National
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.
$333 nightly
The price is $371
Jul 1 - Jul 2
Total with taxes and fees
Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches
On the beach

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (102 reviews)
"Beautiful sunset view. "
United States
Rhonda V.
$312 nightly
The price is $347
Jul 26 - Jul 27
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA
Marina

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.
$466 nightly
The price is $483
Jul 9 - Jul 10
Total with taxes and fees
Waterfront Condo Walkable to Everything with Beach Access
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, (96 reviews)
"Great view, clean, beautiful!"
United States
Bethany
$392 nightly
The price is $437
Jul 12 - Jul 13
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)
"Loved the location, near all the best restaurants and golf. Condo was well equipped and provided all the essentials. Especially loved the soth facing lani to give us full sun all day."
United States
Jenny J.
$254 nightly
The price is $283
Jul 8 - Jul 9
Total with taxes and fees
Shorewalk Sunny Bella Rosa • 2BR Villa • 2 Pools & Hot Tubs • Near IMG / Beaches
Property grounds

Heated Pool Apartment Near Siesta Key 1BR

Heated Pool Apartment Near Siesta Key 1BR
Sarasota
9.2 out of 10, Wonderful, (47 reviews)
"Great location for my interests. My life long indoor cat loved the lanai.The host was kind and helpful in local suggestions .The accommodations was clean and comfortable. I would not hesitate to return . "
United States
Kathy B.
$292 nightly
The price is $326
Jul 3 - Jul 4
Total with taxes and fees
Heated Pool Apartment Near Siesta Key 1BR
On the beach

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (79 reviews)
"The cabana was a fantastic place to escape. It had easy access to both the beach and the pool. My kids loved every moment there."
United States
Roxana P.
$279 nightly
The price is $311
Jul 15 - Jul 16
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,272 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
$177 nightly
The price is $197
Jul 7 - Jul 8
Total with taxes and fees
Captiva Beach Resort
Beach nearby, sun loungers, beach towels

Spacious Waterfront Condo · Pools & Hot Tubs · IMG Academy · Anna Maria Island

Spacious Waterfront Condo · Pools & Hot Tubs · IMG Academy · Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (130 reviews)
"It was a perfect location, looked exactly like the pictures and the host did everything to make our stay great!"
United States
Martha B.
$285 nightly
The price is $318
Jul 26 - Jul 27
Total with taxes and fees
Spacious Waterfront Condo · Pools & Hot Tubs · IMG Academy · Anna Maria Island
On the beach

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (82 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
$550 nightly
The price is $613
Jul 23 - Jul 24
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA
On the beach, beach umbrellas

Gulf Front Escape – Silver Sands #252 by RVA

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.2 out of 10, Wonderful, (104 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
$323 nightly
The price is $360
Jul 1 - Jul 2
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA
On the beach, beach umbrellas

Relax, Recharge & Repeat – Silver Sands #241 by RVA

Relax, Recharge & Repeat – Silver Sands #241 by RVA
Longboat Key
9.4 out of 10, Exceptional, (42 reviews)
"Great location! Beach steps away. Relaxing pool. Clean unit"
United States
Deborah F.
$391 nightly
The price is $436
Jul 25 - Jul 26
Total with taxes and fees
Relax, Recharge & Repeat – Silver Sands #241 by RVA
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

Lantern Inn & Suites

Lantern Inn & Suites

8/10 Good
"This hotel doesn't look like anything special from the road. However, the rooms were well kept and comfortable. Everything was clean and in good shape. The room had a Keurig coffee maker, refrigerator, etc. -- Probably the coolest feature of the hotel is an outdoor Tiki bar, which has several TV's. No breakfast is offered at this hotel, so if that's important to you, book elsewhere. Otherwise, for the money, this was a decent place to stay."
Christopher 1-night trip
Posted 1 hour ago
Lantern Inn & Suites

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,950
Accommodation
3755 Condo Rentals
Lowest Price
$197
Highest Price
$1,958

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $197 to $1,958 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 9.3. 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 3755 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 $197 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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