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Compare 2978 Condo Rentals in Osprey with updated reviews, rates, and availability.

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1074)
"Cute place! Lower Kitchen cabinets were built wrong and opened up and hit the dishwasher handle "
The price is AED 1,087
AED 1,353 total
includes taxes & fees
13 Mar - 14 Mar
Captiva Beach Resort

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (2)
"Very friendly service!! Jim was amazing ! "
The price is AED 641
AED 1,452 total
includes taxes & fees
10 Apr - 11 Apr
Chadwick Cove Resort & Marina

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (403)
"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

Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key

9.0 out of 10, Wonderful, (53)
"Stay was comfortable."
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key

The Sapphire Suite 1Bed/1Bath

9.8 out of 10, Exceptional, (67)
"The property is beautiful. The bed was very comfortable. It looks exactly as the pictures and we had a wonderful stay here we would definitely rent again."
The price is AED 312
AED 571 total
includes taxes & fees
9 Apr - 10 Apr
The Sapphire Suite 1Bed/1Bath

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

9.8 out of 10, Exceptional, (47)
"It was close to everything we wanted to do this time in Sarasota bring right off 41."
The price is AED 455
AED 765 total
includes taxes & fees
31 Mar - 1 Apr
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"The property pictures are accurate. You can see the ocean and beach clearly, doors open four-fold. We give Venice Island grace right now as it is healing, lots of sand, lots of destruction. This unit was not damaged, had super comfortable seating, beds. New pillows, bedding, soft towels. The supplies were abundant! Tons of kitchen items, spices, drinks, kitchen stapes, paper products, etc. Hosts are outstanding, willing to provide upon a phone call. We were very impressed with the owners and the...
Beach Front View 2 Bed, 2 Bath, Condo with AC & WiFi in Fabulous Venice!

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#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. "
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!

10.0 out of 10, Exceptional, (27)
"We were thrilled with the condo, the beach and the area! The condo was exactly as described, plus the added bonus of beach equipment. The proximity to the beach was ideal. We would absolutely stay here again. "
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (55)
"Located in a safe, well-maintained, but lower middle class neighborhood, this property has been beautifully re-done interioraly, and the grounds are well maintained. patio is delightful. I'd stay here again if in SW Florida."
Casa Azul 2Bed/1Bath

Riverside Oasis 1Bed/1Bath

9.4 out of 10, Exceptional, (23)
"The space was clean and well decorated. The bed was comfortable but small. I didn’t love the curtains on the glass door. They are too small and do not completely cover the door. While the room was very clean, the cleaners had used strong bleach and the smell was over powering. The space is cozy for two people and on a quiet street. It is near town and convenient to local businesses. Overall it was very nice. "
The price is AED 356
AED 621 total
includes taxes & fees
2 Apr - 3 Apr
Riverside Oasis 1Bed/1Bath

Saltwater Serenity - Beachfront, Pool Access, Walk to Restaurants & Live Music

10.0 out of 10, Exceptional, (1)
"This was, hands down, our best visit and best rental in Manasota. The stairs were a bit daunting at first, but the amazing views made the climb worth the effort. Everything in the unit felt new, fresh and clean. Each of the 3 balconies has a lovely view of the gulf or the bay, so sunrises and sunsets were wonderful. We very much appreciated the pool on the few days where red tide made the beach impossible. Overall, we had such a great time that we have already booked for 2026."
Saltwater Serenity - Beachfront, Pool Access, Walk to Restaurants & Live Music

Unit 68 - 1 Bedroom and 1 Bathroom Condominium with Partial South Views

9.6 out of 10, Exceptional, (81)
"Clean, great location. May sound funny but great amount of hangers and hooks!!!!!!!"
Unit 68 - 1 Bedroom and 1 Bathroom Condominium with Partial South Views

Siesta Key Voted #1 Beach Siesta Dunes 2 Bedroom Condo Beautiful Beach Book Now

9.8 out of 10, Exceptional, (114)
"Best place to be in Jan-Mar. Perfect location to everything. Property is very well maintained, and the staff is exceptional. Absolutely a beautiful Paradise."
Siesta Key Voted #1 Beach Siesta Dunes 2 Bedroom Condo Beautiful Beach Book Now

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

9.4 out of 10, Exceptional, (103)
"We found this to be our absolute favorite place yet!! It is PERFECT for us. It was clean and you cannot beat the location. We hope to stay again this time next year. THANK YOU. "
Sand in Your Toes . . . Right Out Your Front Door!

☀️ Beachfront. Gulf View from Every Room, Beach & Pool Open, Sunset View, CLEAN

10.0 out of 10, Exceptional, (69)
"Despite the recent hurricanes, the property and the island were in remarkable shape! The condo is beautiful and had everything we needed plus more. The hosts were very quick to respond to messages we sent with questions. We will definitely choose this location for our next girl’s trip to Siesta Key!"
☀️ Beachfront. Gulf View from Every Room, Beach & Pool Open, Sunset View, CLEAN

7th-Floor Oceanfront Palm Beach Club Condo | Stunning Views | Heated Pool | Prime Location!

9.6 out of 10, Exceptional, (90)
"We stayed late-Dec / early-Jan and had an absolutely amazing trip. The condo is exactly as advertised and was perfectly clean upon arrival. Check-in was very easy and instructions were very clear. The master king bed is very comfortable; one of the best my wife and I have slept in staying at a VRBO. The kids room is nice and connects to the 2nd bathroom. Views from both bedrooms are fantastic. Our girls are 4.5 and 1.5 and the unit was perfect for them. Kitchen has everything you need for all...
7th-Floor Oceanfront Palm Beach Club Condo | Stunning Views | Heated Pool | Prime Location!

Charming Siesta Key Village Vacation Condo - Unbeatable Location, Free WiFi

9.2 out of 10, Wonderful, (82)
"This condo had everything we needed! The loaded cart/wagon was such a nice addition & unexpected - thank you! It was close to the beach (2 blocks) & Siesta Village. It was nicely furnished & very comfortable. We loved the keyless entry! The pool was nice too."
Charming Siesta Key Village Vacation Condo - Unbeatable Location, Free WiFi

Beautifully furnished condo

9.8 out of 10, Exceptional, (125)
"The apartment was great...just as advertised. It was well stocked with household items....towels, dishes, etc. The community has two pools and two hot tubs that we used frequently. Also has pickle ball and tennis courts that we did not use. The only issue was when we got to the apartment it had not been cleaned from the previous stay. I messaged the owner and they were very responsive and helpful in getting it rectified as well as a small refund on the cleaning fee for the issue. Would...
The price is AED 496
AED 1,060 total
includes taxes & fees
27 Mar - 28 Mar
Beautifully furnished condo

Lovely Waterfront Condo! Two Pools~Lanai~WiFi. Near IMG~Beaches~AMI~Restaurants.

10.0 out of 10, Exceptional, (103)
"This was our second visit to this condo and we enjoyed it as much as the first time. It is quiet, clean and comfortable."
Lovely Waterfront Condo! Two Pools~Lanai~WiFi. Near IMG~Beaches~AMI~Restaurants.
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

3.5 star property
9.4 out of 10, Exceptional, (4580)
"Very nice accommodation and staff. We will stay there again."
The price is AED 846
AED 1,039 total
includes taxes & fees
1 Apr - 2 Apr
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2096)
"We enjoyed our stay. Staff was extremely nice and helpful. Room was clean but a few things like the couch, blankets could be updated or replaced. "
The price is AED 868
AED 981 total
includes taxes & fees
13 Mar - 14 Mar
Hibiscus Suites - Gateway to Siesta Key

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (235)
"❤️"
The price is AED 334
AED 585 total
includes taxes & fees
1 Apr - 2 Apr
Tiny House Siesta
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 AED 312 to AED 1,087 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?
Osprey has multiple condos with a total average guest review rating of 9.6. Venice Beach Villas is one highly recommended option. Guests of this 3-star condo will have use of a barbecue grill and an electric car charging station. 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?
Work out your vacation dates and then pick from 2978 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.
Are there any 5-star condos in Osprey?
Osprey unfortunately doesn’t have any 5-star condos — but you and the crew can still enjoy a stylish getaway! Why not try Gulf Holiday By Beachside Management? Located about 11 kilometers from downtown, this 4-star property offers concierge services and a swimming pool. Jamaica Royale - 028 - 1 Bedroom Condo is another great choice just 10 kilometers from the center of Osprey. Also with a 4-star rating, it comes with a furnished patio and a patio.
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.