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Our top choices for Osprey condo rentals

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (74 reviews)
"Was good. Decent place to work remotely. Open to better rate in the future to stay for a month."
United States
Dan S.
Relax at Gulf – Silver Sands Resort #232, Longboat

Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (74 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The condo was clean and had all that we needed for our two night stay. Loved it will be back again... just a little walk to the beach and some he pool was very nice as well."
United States
Nancy C.
Newly Renovated 1BR – Cabana Beach #5 RVA

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (16 reviews)
"Great place and location "
United States
Cathy
The price is €645
includes taxes & fees
31 Mar - 1 Apr
Chadwick Cove Resort & Marina

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear
Sarasota
9.6 out of 10, Exceptional, (14 reviews)
"We had a lovely week in this property and even saw some dolphins swimming by!"
United States
Hilda H.
The price is €575
includes taxes & fees
10 Mar - 11 Mar
Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
Longboat Key
8.6 out of 10, Excellent, (18 reviews)
"This was amazing ! It was just as pictured! Everything was new and clean on the property and the beach was 10 feet outside your door. "
United States
Jeremy P.
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to 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, (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
The price is €287
includes taxes & fees
11 Mar - 12 Mar
Oceanfront Bliss–Longboat Key Beach 106 by RVA

Silver Sands Serenity – Unit 234 by RVA

Silver Sands Serenity – Unit 234 by RVA
Longboat Key
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.
The price is €302
includes taxes & fees
15 Mar - 16 Mar
Silver Sands Serenity – Unit 234 by RVA

Riverside Oasis 1Bed/1Bath

Riverside Oasis 1Bed/1Bath
Bayou Oaks
9.2 out of 10, Wonderful, (46 reviews)
"Excellent place to stay"
United States
garry s.
The price is €130
includes taxes & fees
22 Mar - 23 Mar
Riverside Oasis 1Bed/1Bath

Beautiful 2BR Condo: Heated Pools~Fast WiFi. By IMG~Beaches~AMI~SRQ~Restaurants.

Beautiful 2BR Condo: Heated Pools~Fast WiFi. By IMG~Beaches~AMI~SRQ~Restaurants.
Bradenton
9.8 out of 10, Exceptional, (151 reviews)
"Great location, clean, everything we needed for a low key beach vacation!"
United States
Stephanie H.
The price is €309
includes taxes & fees
4 Apr - 5 Apr
Beautiful 2BR Condo: Heated Pools~Fast WiFi. By IMG~Beaches~AMI~SRQ~Restaurants.

Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Bradenton
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.
The price is €378
includes taxes & fees
25 Mar - 26 Mar
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
7.8 out of 10, Good, (7 reviews)
"Great locale right on the beach "
United States
Carole
Beachfront Bliss on Longboat Key- Steps to the sand

Beautifully furnished condo

Beautifully furnished condo
Bradenton
9.8 out of 10, Exceptional, (154 reviews)
"We would stay there again."
United States
Connie S.
The price is €278
includes taxes & fees
31 Mar - 1 Apr
Beautifully furnished condo

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Bradenton
9.8 out of 10, Exceptional, (136 reviews)
"The condo was cleaned and well maintained. "
United States
Scott Z.
The price is €412
includes taxes & fees
13 Mar - 14 Mar
*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

Coastal Breeze Siesta - Turtle

Coastal Breeze Siesta - Turtle
2.0 star property
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"Great little place to stay and enjoy the nearby beaches and restaurants! The communication was on point. We will be back "
United States
Jacob
The price is €545
includes taxes & fees
1 Apr - 2 Apr
Coastal Breeze Siesta - Turtle

1BR Beach Oasis – Silver Sands #258, Longboat Key by RVA

1BR Beach Oasis – Silver Sands #258, Longboat Key by RVA
Longboat Key
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.
1BR Beach Oasis – Silver Sands #258, Longboat Key by RVA

Vitamin Sea Escape: Open Wed, March 18th!

Vitamin Sea Escape: Open Wed, March 18th!
Longboat Key
10.0 out of 10, Exceptional, (88 reviews)
"The perfect beach cottage for our wedding anniversary. We had everything we needed including beautiful weather ."
United States
Julie Q.
The price is €387
includes taxes & fees
18 Mar - 19 Mar
Vitamin Sea Escape: Open Wed, March 18th!

2BR Beach & Trolley–Beach Club Siesta 204B by RVA

2BR Beach & Trolley–Beach Club Siesta 204B by RVA
South Village
8.6 out of 10, Excellent, (42 reviews)
"Would definitely stay there again"
United States
Nini R.
2BR Beach & Trolley–Beach Club Siesta 204B by RVA

Seaside Escape – Beach Castle #24 by RVA

Seaside Escape – Beach Castle #24 by RVA
Longboat Key
9.2 out of 10, Wonderful, (47 reviews)
"Loved staying here"
United States
James
The price is €384
includes taxes & fees
9 Mar - 10 Mar
Seaside Escape – Beach Castle #24 by RVA

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, (32 reviews)
"It was an amazing accommodation!! I hope to stay there each time I visit!!!!!!"
United States
Anonymous traveller
The price is €396
includes taxes & fees
24 Mar - 25 Mar
Shorewalk Palms Heaven 2BR Villa • 2 Pools & Heated Hot Tubs •Near IMG / Beaches

3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf

3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf
Manasota Key
9.6 out of 10, Exceptional, (61 reviews)
"We just needed to get away. This was the prefect spot. We would definitely come back. The view of the water was amazing "
United States
Angela S.
The price is €587
includes taxes & fees
8 Mar - 9 Mar
3 Bedroom-Beachfront Condo with Most 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.
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Top Osprey Hotel Reviews

Find out more about Osprey

Osprey Condo Rentals information

Number of reviews
1,172
Accommodation
3535 Condo Rentals
Lowest Price
€130
Highest Price
€645

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from €130 to €645 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 travelling 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 holiday dates and then pick from 3535 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 €130 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 favourite 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 accommodation that have what you're looking for. Located about 11 kilometres 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 8 kilometres from the centre 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 travellers alike.