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Compare 3019 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, (1061)
"Beautiful property. Walk to beach. "
The price is SAR 868
SAR 1,109 total
includes taxes & fees
5 Jan - 6 Jan
Captiva Beach Resort
Venice Beach Villas
Pool

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (401)
"We’ve stayed here before and it was an easy decision to book again. The location is perfect, it’s quiet and the manager that booked us in was so nice. We’ll be back and recommend it to anyone else looking for a place to stay in Venice. "
Venice Beach Villas
5 Minutes from Siesta Key!
Living area

5 Minutes from Siesta Key!

9.8 out of 10, Exceptional, (14)
"We had a great, quick stay. The bedrooms were spacious, and house very clean! Right off a busy road, easy to get to the beach. "
5 Minutes from Siesta Key!
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, (116)
"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, (99)
"We enjoyed our staff. It was just right for what we were looking for. "
*Casa Mia* Fabulous 2BR Condo w/2Pools, Mins to IMG/Beach/Anna Maria Isl
Panoramic beach View and amazing Sunset.
Living area

Panoramic beach View and amazing Sunset.

9.8 out of 10, Exceptional, (95)
"Beautiful unit!"
Panoramic beach View and amazing Sunset.
Paradise 🏝Beach heaven 🌞condo 🦩<br>
Living area

Paradise 🏝Beach heaven 🌞condo 🦩<br>

10.0 out of 10, Exceptional, (33)
"Condo was very clean and has enough room for 8 people. Very spacious. "
Paradise 🏝Beach heaven 🌞condo 🦩<br>
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Beautiful Lido Key Beach

Vacation delight! Cozy condo just steps from the beach and St. Armands circle.

10.0 out of 10, Exceptional, (127)
"Sue worked very hard on restoring this property after the hurricanes. It was beautiful on the inside. It was very spacous with all new furnishings. The location is within walking distance to the beach, food, drinks, and shopping. The only downside was having to leave. We cannot recommend this place enough."
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Beautiful Condo! Heated Pools~WiFi~A/C. By IMG Academy~Beaches~AMI~Restaurants.
Angle view of the large pool. A great place to catch a tan or take a swim.

Beautiful Condo! Heated Pools~WiFi~A/C. By IMG Academy~Beaches~AMI~Restaurants.

9.8 out of 10, Exceptional, (127)
"We enjoyed our stay at this condo. It was clean, comfortable, and looked like the pictures. Grocery store and pharmacy within walking distance. The pool we used was nice and well maintained. Would stay here again. "
The price is SAR 469
SAR 1,274 total
includes taxes & fees
6 Jan - 7 Jan
Beautiful Condo! Heated Pools~WiFi~A/C. By IMG Academy~Beaches~AMI~Restaurants.
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, (130)
"Overall good property. Needs a gym and hot tub and a volleyball net out on the sand would be fun. Very friendly staff, good pool, great beach. "
Breathtaking Beach Front Property Ground Floor Condo
Beach view. Year-round Balcony Sunsets. Just renovated.
Property grounds

Beach view. Year-round Balcony Sunsets. Just renovated.

9.8 out of 10, Exceptional, (75)
"Beautiful view.. home was clean and the front staff was amazing. "
The price is SAR 657
SAR 1,530 total
includes taxes & fees
5 Jan - 6 Jan
Beach view. Year-round Balcony Sunsets. Just renovated.
Luxury Beach Condo with Breathtaking PROMO AUGUST- 2024 -175- NIGHT BEST PRICE!
Property grounds

Luxury Beach Condo with Breathtaking PROMO AUGUST- 2024 -175- NIGHT BEST PRICE!

9.8 out of 10, Exceptional, (230)
"This property is so special. Right on the beach and with only 4 units in the building it feels like your own private beach. The unit itself is large, clean and nicely decorated. I look forward to staying here again. "
Luxury Beach Condo with Breathtaking PROMO AUGUST- 2024 -175- NIGHT BEST PRICE!
Beach View Condo- Quiet & Secluded with Private Beach
Beach

Beach View Condo- Quiet & Secluded with Private Beach

10.0 out of 10, Exceptional, (21)
"10/10! We stayed at this property Nov 21-26 (my mom, 2 boys age 5 and 7, and myself). The property was easy to get to (25 min drive from Sarasota-Bradenton), check-in was effortless (host sent a code), and the property was very clean and quiet. When you see how close the beach is in the pictures, that truly is how close it is! The chairs on the beach were super convenient. The seller was an excellent communicator! She kept in touch with us after the hurricane and was upfront about issues caused...
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, (29)
"I had a very pleasant say and the manager was able to help me with the A/C in the room"
*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Siesta Key Condo Siesta Breakers
Exterior

Siesta Key Condo Siesta Breakers

10.0 out of 10, Exceptional, (11)
"Clean property and excellent location. Rental was just as described."
Siesta Key Condo Siesta Breakers
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
View of our private beach area

DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.

10.0 out of 10, Exceptional, (69)
"All we can say is WOW! The property was exactly as described. The view was AMAZING and it was exactly what we needed...quiet, peaceful and relaxing!! Loved the SUNSETS!"
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
Beach Front View 2 Bed, 2 Bath, Condo with AC & WiFi in Fabulous Venice!
Beach

Beach Front View 2 Bed, 2 Bath, Condo with AC & WiFi in Fabulous Venice!

2.0 star property
Beach Front View 2 Bed, 2 Bath, Condo with AC & WiFi in Fabulous Venice!
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, (7)
"It was a great time! "
Siesta Key 4th Floor Condo, Facing Gulf of Mexico 2B/2B
Sand in Your Toes . . . Right Out Your Front Door!
The beach out front!

Sand in Your Toes . . . Right Out Your Front Door!

9.4 out of 10, Exceptional, (97)
"The unit is clean, well decorated and has all the necessities. Right on the sand. Enjoyed having coffee on the rocking chairs in the morning. Manasota key is one of the most beautiful areas in southwest Florida. The recovery from the hurricane is underway. It’s amazing that this unit is in such great condition.! I highly recommend it owners are great!"
Sand in Your Toes . . . Right Out Your Front Door!
Paradise! Remodeled 2 bedroom 2 bathroom with incredible views
View from living room

Paradise! Remodeled 2 bedroom 2 bathroom with incredible views

9.8 out of 10, Exceptional, (140)
"This property is the best! We have loved staying here over the past few years and look forward to next year already. The owner is wonderful to work with!"
Paradise! Remodeled 2 bedroom 2 bathroom with incredible views
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, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
The price is SAR 674
SAR 846 total
includes taxes & fees
20 Jan - 21 Jan
Tropical Beach Resorts
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
9.8 out of 10, Exceptional, (220)
"Very lovely (and large!) accommodation. Extremely clean. Front desk staff kind of rude/pretentious.Great location right on the beach at Siesta Key. Heated pool with good poolside bar. Also had a hot tub, which was nice as the weather was a bit cool when we were there. Feel like I was misled a bit based on room description--thought we were booking a room with beach view, but instead got "city view"--which essentially looked into a back alley and at a 7-eleven. For the price/my personal budget,...
The price is SAR 1,836
SAR 2,266 total
includes taxes & fees
16 Jan - 17 Jan
The Residences at Siesta Key Beach by Hyatt Vacation Club
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2081)
"Just over the bridge from the Key, stores with in walking distance. Room had a full size refrigerator! Two burner stove pots and pans and local super market not far, no need to eat out every night. The building has been upkept suprisingly very nice , and the staff was very helpful if anything came up. The area is a little older but overall you cant beat the value here. Oh yeah the pool was nice and hey have a grill you can use. "
The price is SAR 559
SAR 632 total
includes taxes & fees
6 Jan - 7 Jan
Hibiscus Suites - Gateway to Siesta Key
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 SAR 469 to SAR 868 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 offers multiple condos with a total average guest review rating of 9.6. Venice Beach Villas is a top 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 a winner with travelers to the area. This 3-star property has a deck and a lanai.
How many condos are there in Osprey?
Choose from 3019 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 4-star accommodations that will fit your needs. Located around 11 kilometers from downtown, Gulf Holiday By Beachside Management comes with a swimming pool and concierge services. Another upscale stay is Jamaica Royale - 302 - 2 Bedroom Condo. It’s around 10 kilometers from central Osprey and features amenities such as a swimming pool and a balcony.
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.