Search and Rent Osprey Condos

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In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Osprey condo rentals

Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
$345 nightly
The price is $386
Apr 15 - Apr 16
Total with taxes and fees
Chadwick Cove Resort & Marina
Beach nearby

Turtle at Coastal Breeze | Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing

Turtle at Coastal Breeze | Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing
Sarasota
10.0 out of 10, Exceptional, (21 reviews)
"Will stay here again."
United States
Anonymous traveler
Turtle at Coastal Breeze | Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing
Property grounds

Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants

Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants
Manasota Key
9.8 out of 10, Exceptional, (33 reviews)
"We had a great time and a comfortable stay."
United States
Deb J.
$362 nightly
The price is $401
Apr 15 - Apr 16
Total with taxes and fees
Beach to Bay! Heated Pool and Dock on the Bay! Walk to the Beach and Restaurants
Property grounds

Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock

Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
Manasota Key
9.8 out of 10, Exceptional, (42 reviews)
"Host was very communicative and helpful. "
United States
Jennifer O.
$346 nightly
The price is $382
Apr 11 - Apr 12
Total with taxes and fees
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
Smart TV

Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (113 reviews)
"Beach view with sunset!!"
United States
joseph l.
$388 nightly
The price is $428
Apr 21 - Apr 22
Total with taxes and fees
Sunset and beach view from your balcony Unit 403
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, (93 reviews)
"Great location, clean, plenty of home essentials."
United States
Charlana W.
$287 nightly
The price is $320
May 1 - May 2
Total with taxes and fees
Shorewalk Sunny Bella Rosa • 2BR Villa • 2 Pools & Hot Tubs • Near IMG / Beaches
Property grounds

Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs

Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (118 reviews)
"Perfect spot and host "
United States
Dee B.
$262 nightly
The price is $292
May 3 - May 4
Total with taxes and fees
Lakefront Condo · IMG Academy 5 Min · Anna Maria Beach 15 Min · Pools & Hot Tubs
On the beach, sun loungers, beach towels

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (78 reviews)
"Beautiful condo and perfect location for a relaxing beach getaway! We celebrated my husband’s 50th birthday and it was perfect! We will definitely book again! "
United States
Yasamin G.
$449 nightly
The price is $497
Apr 19 - Apr 20
Total with taxes and fees
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Property grounds

Lake View Condo! IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Lanai

Lake View Condo! IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Lanai
Bradenton
10.0 out of 10, Exceptional, (124 reviews)
"We enjoyed our stay. Is as shown in pictures and description. "
United States
Erin M.
$271 nightly
The price is $301
May 9 - May 10
Total with taxes and fees
Lake View Condo! IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Lanai
Terrace/patio

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (58 reviews)
"Everything was great. "
United States
Maribel
$135 nightly
The price is $150
Apr 12 - Apr 13
Total with taxes and fees
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Beach nearby

Shorewalk Palms Heaven 2BR Villa • 2 Pools & Heated Hot Tubs •Near IMG / Beaches

Shorewalk Palms Heaven 2BR Villa • 2 Pools & Heated Hot Tubs •Near IMG / Beaches
Bradenton
10.0 out of 10, Exceptional, (35 reviews)
"Great location between beaches and Sarasota activities. Nice space in a lovely community. "
United States
Sara
$270 nightly
The price is $301
Apr 12 - Apr 13
Total with taxes and fees
Shorewalk Palms Heaven 2BR Villa • 2 Pools & Heated Hot Tubs •Near IMG / Beaches
1 bedroom, desk, iron/ironing board, WiFi

Riverside Oasis 1Bed/1Bath

Riverside Oasis 1Bed/1Bath
Bayou Oaks
9.4 out of 10, Exceptional, (52 reviews)
"This little getaway was an anniversary celebration and it felt like we were in the perfect place to celebrate 15 years of marriage .This beautiful little house was extra clean , cozy, well decorated and well equipped, with the strawberry on top being the peacefulness and tranquillity with a short 15 min ride to the nearest beach and city center. We highly recommend the place."
United States
Juan
$110 nightly
The price is $122
Apr 29 - Apr 30
Total with taxes and fees
Riverside Oasis 1Bed/1Bath
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.
$607 nightly
The price is $677
Apr 30 - May 1
Total with taxes and fees
Unlimited Golf with membership transfer- Lakewood National
Sun loungers

*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Bradenton
9.8 out of 10, Exceptional, (58 reviews)
"Host was very responsive and provided helpful information for our stay."
United States
Azure G.
$353 nightly
The price is $393
Apr 14 - Apr 15
Total with taxes and fees
*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
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, (12 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
$299 nightly
The price is $333
May 1 - May 2
Total with taxes and fees
Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN
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, (128 reviews)
"We had a pleasant stay! Very nice location! Close to everything. The host, Richard, was very helpful. Would definetely stay again "
United States
Marilu R.
$298 nightly
The price is $333
May 11 - May 12
Total with taxes and fees
*Casa Mia* Fabulous 2BR Condo w/2Pools, Mins to IMG/Beach/Anna Maria Isl
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, (89 reviews)
"Breathtaking view- super clean. Easy access. Perfect spot for a few days away with my husband."
United States
Ellen L.
$380 nightly
The price is $418
Apr 30 - May 1
Total with taxes and fees
Best views of the beach from your balcony Unit 301
On the beach, beach umbrellas

Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA

Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA
Longboat Key
9.2 out of 10, Wonderful, (77 reviews)
"Property was as indicated. Office staff was very friendly and accommodating. Property was quiet.We were just steps from the direct beach access."
United States
Leen S.
$310 nightly
The price is $346
May 11 - May 12
Total with taxes and fees
Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA
Beach

Bright Corner Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Two Pools

Bright Corner Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Two Pools
Bradenton
9.8 out of 10, Exceptional, (154 reviews)
"Condo was great, beds were comfortable!"
United States
CATHY T.
$262 nightly
The price is $293
Apr 27 - Apr 28
Total with taxes and fees
Bright Corner Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Two Pools
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, (78 reviews)
"Was good. Decent place to work remotely. Open to better rate in the future to stay for a month."
United States
Dan S.
$312 nightly
The price is $349
Apr 13 - Apr 14
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Great outdoor pool and hot tub, very friendly accommodating staff , great location ! Would definitely recommend and come back!"
Vincent 4-night trip
Posted 1 hour ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,361
Accommodation
3628 Condo Rentals
Lowest Price
$122
Highest Price
$677

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from $122 to $677 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 9.8. 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 $122 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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