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

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
The price is £444
includes taxes & fees
5 Jul - 6 Jul
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.
The price is £233
includes taxes & fees
30 Jun - 1 Jul
Waterfront Condo w/ Lanai · Pools & Hot Tubs · IMG Academy · Anna Maria Island
Outdoor pool, pool umbrellas, pool 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
The price is £474
includes taxes & fees
13 Jul - 14 Jul
Cedar Run Resort - Roam Hospitality
Beach nearby, sun-loungers, beach towels, snorkelling

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.
The price is £374
includes taxes & fees
2 Jul - 3 Jul
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
The price is £260
includes taxes & fees
30 Jun - 1 Jul
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
The price is £270
includes taxes & fees
12 Jul - 13 Jul
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)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
The price is £241
includes taxes & fees
2 Jul - 3 Jul
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.
The price is £283
includes taxes & fees
1 Jul - 2 Jul
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.
The price is £293
includes taxes & fees
6 Jul - 7 Jul
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.
The price is £397
includes taxes & fees
13 Jul - 14 Jul
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
The price is £299
includes taxes & fees
12 Jul - 13 Jul
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.
The price is £236
includes taxes & fees
25 Jul - 26 Jul
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.
The price is £255
includes taxes & fees
3 Jul - 4 Jul
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.
The price is £237
includes taxes & fees
15 Jul - 16 Jul
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
The price is £170
includes taxes & fees
6 Jul - 7 Jul
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.
The price is £242
includes taxes & fees
26 Jul - 27 Jul
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.
The price is £353
includes taxes & fees
30 Jun - 1 Jul
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.
The price is £293
includes taxes & fees
30 Jun - 1 Jul
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.
The price is £303
includes taxes & fees
30 Jun - 1 Jul
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Very clean and beautiful"
Veronika 1-night trip
Posted less than an hour ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
2,493
Accommodation
3650 Condo Rentals
Lowest Price
£170
Highest Price
£474

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from £170 to £474 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?
We recommend Venice Beach Villas. Kick back at this 3-star property which comes with a terrace and therapeutic mineral springs. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is another highly rated condo worth looking into. Spend your holiday at this popular 3-star option and you'll have access to amenities including a deck and a lanai. You can choose from multiple condos in Osprey with a total average guest review rating of 9.4.
How many condos are there in Osprey?
Work out your holiday dates and then pick from 3650 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?
Captiva Beach Resort is one of the best inexpensive condos in Osprey and includes pillow top mattresses and premium bedding. Another popular choice that's easy on the budget is Bs 1350 - #1 Siesta And Crescent Beach Are Walking Distance Away. It features a barbecue grill and a swimming pool. Rates for condos start from only £170 per night. If you want to save your hard-earned cash and still experience the best of Osprey, add a couple of awesome free attractions to your to-do list. Manasota Beach and Sarasota National Cemetery are always popular among visitors. 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?
Many visitors needing family-friendly condos in Osprey go for Venice Beach Villas. With a 3-star rating and amenities including therapeutic mineral springs and a barbecue grill, it'll feel like your home away from home. Or, consider 3-star Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village. A deck and a lanai help make it an ideal base for your Osprey getaway. Osprey has lots of family-friendly attractions to explore when the kids are getting restless. Manasota Beach and Heritage Oaks Golf and Country Club promise fun for everyone.
Are there any 5-star condos in Osprey?
You won't find any 5-star condos in Osprey. However, you will find some comfortable 4-star stays that have this feature. Check in to Gulf Holiday By Beachside Management, about 7 mi from downtown. a swimming pool and concierge services are a couple of the many conveniences included here. Jamaica Royale - 028 - 1 Bedroom Condo is another upmarket option. It comes with a furnished patio and a nearby seaside and is located around 6 mi from the centre of Osprey.
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 travellers alike.