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Compare 2960 Condo Rentals in Osprey with updated reviews, rates, and availability.

Captiva Beach Resort
Front of property - evening/night
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, (1057)
"Nice and quiet place, close to the beach and dining places."
Captiva Beach Resort
Venice Beach Villas
Pool
Venice Beach Villas
3.0 star property
9.4 out of 10, Exceptional, (394)
"I love the quiet and relaxing atmosphere and great pool. This charming oasis is situated just steps from shops and dining options and an extremely enjoyable short walk to Venice Beach. The Pavilion at the beach is a great place to grab a drink or quick lunch and people watch. I love Venice Beach Villas and will return as often as I get the chance! Thanks Ken!"
Venice Beach Villas
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
View from the lanai. Pool is on the left.
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
9.8 out of 10, Exceptional, (235)
"Despite the order to evacuate for the hurricane we enjoyed our stay in the condo. The location was great and it was nice to be close to parking and the ground level. Thanks to Lynn for a refund for the rest of the stay. I appreciate it as I did not expect it."
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US
Private Beach access right outside Your front door
WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US
10.0 out of 10, Exceptional, (114)
"Very nice. Clean "
WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US
*Casa Mia* Fabulous 2BR Condo w/2Pools, Mins to IMG/Beach/Anna Maria Isl
Living area
*Casa Mia* Fabulous 2BR Condo w/2Pools, Mins to IMG/Beach/Anna Maria Isl
9.8 out of 10, Exceptional, (95)
"Enjoyed the property! Clean and great location . Check in a breeze . Owner very organized and informative during our stay. Thanks "
*Casa Mia* Fabulous 2BR Condo w/2Pools, Mins to IMG/Beach/Anna Maria Isl
Breathtaking Beach Front Property Ground Floor Condo
Gulf of Mexico on Longboat Key
Breathtaking Beach Front Property Ground Floor Condo
9.6 out of 10, Exceptional, (128)
"Upscale, very well kept condo with all the necessary items for a pleasant vacation. Quality towels and linen. Very clean and tastefully decorated. No clutter. Highly recommend."
Breathtaking Beach Front Property Ground Floor Condo
Renovated! Private Beachfront Complex with 3 Pools
New furnishings in the living and dining area. Smart TV including cable & WiFi
Renovated! Private Beachfront Complex with 3 Pools
9.4 out of 10, Exceptional, (23)
"The condo was just as described. It had everything we needed for our stay including starter supplies. The trolly service is fantastic and dropped off passengers directly in from of the complex when we picked it up. They dropped us off there again later that evening. The unit is close to the grill which we loved. The only complaint we had was that the thermostat was unable to be set any lower than 73 degrees. As Floridians, we typically lower our temp from 75 during the day to 69 at night. We...
Renovated! Private Beachfront Complex with 3 Pools
On beach, View, pool, beautifully remodeled professionally managed
Livingroom 5 leather recliners
On beach, View, pool, beautifully remodeled professionally managed
9.8 out of 10, Exceptional, (88)
"We had a nice time at this condo. All the chairs in the living area were a nice bonus. The location was great. We didnt really use the deck at all so cant comment on it. The refrigerator was connected to the hot water . If you are not the first one to get water you get hot water . Also the king bed was very uncomfortable for us. I know everyone is different but our experience was not that pleasant. The kids beds were good though. Also your only allowed in a little section of the beach. ...
On beach, View, pool, beautifully remodeled professionally managed
Casa Del Mar Longboat Key
Living area
Casa Del Mar Longboat Key
4.0 star property
9.4 out of 10, Exceptional, (159)
"A pleasant peaceful stay."
Casa Del Mar Longboat Key
Siesta Key 4th Floor Condo, Facing Gulf of Mexico 2B/2B
Living area
Siesta Key 4th Floor Condo, Facing Gulf of Mexico 2B/2B
10.0 out of 10, Exceptional, (5)
" Booked our unit 48 hours ahead, due to an unforseen issue with our prior booking. We found this gem and had a great week."
Siesta Key 4th Floor Condo, Facing Gulf of Mexico 2B/2B
Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.
Romantic Getaway
Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.
9.8 out of 10, Exceptional, (137)
"Cute little cottage with 2br, 1ba. Very clean, close to the beach. Lots of supplies for the beach. Could use softer towels in bathroom and perhaps some instructions on the shower as it was quite hot on any setting. Prior communication was slow but once there was pretty attentive. "
Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.
Silver Sands on the Gulf!
White sandy beaches for miles
Silver Sands on the Gulf!
10.0 out of 10, Exceptional, (64)
"Our stay was amazing! A perfect beach condo for a family with young kids, short walk to the beautiful beach & pool! Heidi was a wonderful host, very thorough & so kind! This was our first visit to Longboat Key, we loved it! Would highly recommend this condo & hope to return in the future! "
Silver Sands on the Gulf!
Beach view. Year-round Balcony Sunsets. Just renovated.
Property grounds
Beach view. Year-round Balcony Sunsets. Just renovated.
9.8 out of 10, Exceptional, (73)
"Beautiful view.. home was clean and the front staff was amazing. "
The price is SAR 582
SAR 1,448 total
includes taxes & fees
23 Oct - 24 Oct
Beach view. Year-round Balcony Sunsets. Just renovated.
Clean, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach
Entrance to complex
Clean, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach
9.8 out of 10, Exceptional, (77)
"The beach area was amazing. Only issue was not many towels for an 8 day stay and the main laundry room was closed for renovations. The beach umbrella, wagon, cooler and chairs is great."
Clean, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach
🏝Beachfront Condo Overlooking Gulf of Mexico🏝 Jetties Pointe Cottage #5
Outdoor dining
🏝Beachfront Condo Overlooking Gulf of Mexico🏝 Jetties Pointe Cottage #5
10.0 out of 10, Exceptional, (10)
"Great view and was able to enjoy the beach in between rain storms. We will come back"
The price is SAR 739
SAR 1,652 total
includes taxes & fees
17 Oct - 18 Oct
🏝Beachfront Condo Overlooking Gulf of Mexico🏝 Jetties Pointe Cottage #5
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN CONDO.
View of our private beach area
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN CONDO.
10.0 out of 10, Exceptional, (65)
"The place is just as it looks in photos. Private beach access with a 15 second walk. Plenty of restaurants and entertainment in the area. We will definitely go back!"
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN CONDO.
Lower Pricing! Private Beach, 2 Heated Pools, Bay Sunrises, Unaffected by Hurricane, Ready to Book!
Comfortable furnishings include a queen sofa sleeper
Lower Pricing! Private Beach, 2 Heated Pools, Bay Sunrises, Unaffected by Hurricane, Ready to Book!
9.4 out of 10, Exceptional, (87)
"Overall we had a great experience, however the place needs a new toaster and utensils, we accommodate based with what we’ve got. "
Lower Pricing! Private Beach, 2 Heated Pools, Bay Sunrises, Unaffected by Hurricane, Ready to Book!
Located Directly on the Gulf of Mexico Beachfront!
Beach
Located Directly on the Gulf of Mexico Beachfront!
8.8 out of 10, Excellent, (60)
"We had a nice stay, just steps from the beach!"
Located Directly on the Gulf of Mexico Beachfront!
Beach View Condo- Quiet & Secluded with Private Beach
Beach
Beach View Condo- Quiet & Secluded with Private Beach
9.8 out of 10, Exceptional, (20)
"I visited Danielle's condo for a 4 night trip with my elderly parents. The condo was clean and well equipped - even had a kettle which pleased my mum greatly. The condo has access to the beach which is less than a 5 minute walk. Free parking was available close to the condo. The resort also has a hot tub and small pool available to use (across the road) Having visited the area before we wanted a more central location with easy access to restaurants, shops and sarasota. This location was super...
Beach View Condo- Quiet & Secluded with Private Beach
*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Living area
*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
10.0 out of 10, Exceptional, (24)
"It was a very comfortable stay with a lovely pool to cool off in. The proximity to the beach and local family was ideal. Our stay in this condo was nice. My only suggestion would be to install an icemaker and maybe supply some more dish towels and dish cloths! Overall, a nice place to stay."
*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
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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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Other property types in Osprey

Tropical Beach Resorts
Outdoor pool
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4535)
"The people who worked there where so pleasant and even the other customers seem to enjoy there stay "
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2070)
"Very clean. Friendly staff. Spacious suite. Though the furniture is not very comfortable. But all in all, it wasn’t too bad if a stay. "
The price is SAR 673
SAR 737 total
includes taxes & fees
9 Oct - 10 Oct
Hibiscus Suites - Gateway to Siesta Key
The Residences at Siesta Key Beach by Hyatt Vacation Club
Exterior
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (208)
"Everyone on the staff was wonderful, fun and friendly! The resort is beautiful and soooo accommodating! "
The price is SAR 1,657
SAR 2,030 total
includes taxes & fees
23 Oct - 24 Oct
The Residences at Siesta Key Beach by Hyatt Vacation Club
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.

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from to per night. This gives you loads of space for the whole family at a price you can afford. 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?
Osprey has multiple condos with a total average guest review rating of 9.5. Venice Beach Villas is a favorite pick here. Guests staying at this 3-star condo will have use of a garden and a barbecue grill. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is also very popular with travelers to the area. This 3-star property features a deck and a lanai.
How many condos are there in Osprey?
Choose from 2960 condos in Osprey. Whether you’re traveling with the little ones or planning a weekend escape with your buddies, Expedia will help you find the best space for your whole crew.
Are there any 5-star condos in Osprey?
Although there aren’t any 5-star condos in Osprey, there are some 4-star accommodations that will fit your needs. Located about 11 kilometers from downtown, Gulf Holiday By Beachside Management comes with concierge services and a swimming pool. Another recommended retreat is Jamaica Royale 205 - 2 Bedroom Condo. It’s around 10 kilometers from central Osprey and offers conveniences like a swimming pool and a lanai.
Why book your condo in Osprey with Expedia?
Booking a condo in Osprey is as simple as entering your travel dates and selecting a place that checks your boxes. On the search for something low cost or luxurious, or a stay that also offers a kitchenette? Use Expedia’s search filters to narrow your results even further and find the perfect fit.
How can I find cheap condos in Osprey?
With Expedia’s handy filter tool, scoring cheap condos in Osprey is a breeze. To discover stays that’ll make your wallet smile, tailor your search results by star rating, amenities and budget.