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Compare 2976 Vacation Homes in Osprey with updated reviews, rates, and availability.

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.6 out of 10, Exceptional, (85)
"Over all great, just never got a response on if the pool was heated or not"
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (223)
"Perfect location to walk to beach and town. The Villas and grounds were well maintained. I wouldnt hesitate staying hefe again."
Tropical Villas of Venice Beach

New home 3/2 renovation 3 miles to Siesta Key

9.2 out of 10, Wonderful, (7)
"This was a really great find. Comfortable beds, close to beach and easy access back to the airport. Only issue was a lot of animal hair was left behind, but easy fix with the vacuum. If we return for vacation we’ll stay again! "
The price is SAR 544
SAR 1,239 total
includes taxes & fees
18 Mar - 19 Mar
New home 3/2 renovation 3 miles to Siesta Key

Casa Azul 2bed/1bath

9.4 out of 10, Exceptional, (54)
"nice place close to the things we wanted to do..ringling museum,beach,yoders restaurant etc.while the house is located in not the best part of town..it was quiet..and clean..and a very good price"
The price is SAR 446
SAR 791 total
includes taxes & fees
10 Mar - 11 Mar
Casa Azul 2bed/1bath

Bohemian Sunrise

10.0 out of 10, Exceptional, (77)
"From the beginning of finding/ choosing this place the whole process was so smooth. Laura was always accessible when we had questions. The place and location are both awesome. The house was super clean and nicely decorated. We loved Manasota key and the area. Due to recent hurricanes the beach is under construction, but some restaurants were open. We traveled a bit to ride bikes and at the end of each day/ night, this place was great to go “home “ to. We will most definitely stay again!!!"
Bohemian Sunrise

Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

9.6 out of 10, Exceptional, (14)
"Cute little home. Host was super communicative & accommodating. Lots of essentials provided. Great stay, thank you! "
Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

Private Heated Pool House 6 miles from the Beach

9.8 out of 10, Exceptional, (219)
"Every step for rental went flawlessly. From check-in to condition of property to eminities. Everything was top notch and I would highly recommend this rental. "
Private Heated Pool House 6 miles from the Beach

Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

8.8 out of 10, Excellent, (5)
"We stayed 2 nights and everything was good. I was Leary booking a vacation from a hotel name for a small condo/ hotel room. This room had 2 queen beds, bathroom and all amenities as a hotel for half the price. Thank you … would recommend this for others that don’t need a high end place. Thanks again"
The price is SAR 296
SAR 622 total
includes taxes & fees
11 Mar - 12 Mar
Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

9.6 out of 10, Exceptional, (114)
"Everything was as expected with the property - however, there was no communication about the cleanup and construction going on all around - I know it was out of your control with the hurricane damage, but I would say that we overpayed for the condition of the area.Lisa did a very good job with communication and the checkin process - Thanks "
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

BRAND NEW EVERYTHING!!!!! 4 bedrooms and sleeps 10 easily.

10.0 out of 10, Exceptional, (14)
"We loved this home. Newly renovated and spacious. We especially liked that half of the house can be closed off for our visiting guest. We would definitely stay here again. "
BRAND NEW EVERYTHING!!!!! 4 bedrooms and sleeps 10 easily.

Private pool House with Fountains & Beach Walkable

9.6 out of 10, Exceptional, (166)
"My mom and I stayed at the Villa for a week and it was amazing!!! Perfect for our needs. Plenty of space, very clean and cozy! Updated throughout and the pool/outdoor space was fantastic. The Villa is located in a great neighborhood-safe, fun and quiet BUT close to awesome hotspot restaurants, the beach and great shopping/ nightlife on Venice avenue. 12/10 recommend will definitely stay again!!"
Private pool House with Fountains & Beach Walkable

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals

Beachside Retreat with Pool and Beach Access

9.0 out of 10, Wonderful, (33)
"See above "
The price is SAR 3,091
SAR 5,463 total
includes taxes & fees
22 Feb - 23 Feb
Beachside Retreat with Pool and Beach Access

Cozy house near Siesta Key Beach

10.0 out of 10, Exceptional, (9)
"This was a last minute VRBO find during peak peak season in Sarasota near the the beach islands and resorts. Couldn’t have been more relieved when we arrived after a 26 hour drive thru heavy traffic, to find a clean, well kept bungalow that had clearly been remodeled and repaired. The place was literally half block away from a very popular seafood restaurant, and not far from the bridges to access the beach islands. (Though in fairness getting to the beaches took awhile simply because of very...
Cozy house near Siesta Key Beach

Charming Private Garden Cottage hide away in the heart of Sarasota

10.0 out of 10, Exceptional, (149)
"We enjoyed our stay here and hopefully we will be back. It is just like the pictures. The owners were great! Thank you for letting us stay at your property!"
Charming Private Garden Cottage hide away in the heart of Sarasota

Beautiful Beach Longboat Key Townhouse

10.0 out of 10, Exceptional, (17)
"The property was perfect for our family ranging in age from 8 months to grandparents. Very comfortable, clean, and cozy. Looking forward to coming back to this property again!"
Beautiful Beach Longboat Key Townhouse

Game Room Florida Home

9.8 out of 10, Exceptional, (16)
"Had eeverything we need and clean and guiet neighborhood"
The price is SAR 413
SAR 1,502 total
includes taxes & fees
10 Mar - 11 Mar
Game Room Florida Home

3 miles to beach, hot tub & fenced yard for pup

10.0 out of 10, Exceptional, (10)
"Very clean and perfect location"
3 miles to beach, hot tub & fenced yard for pup

Spacious coastal retreat with private yard | Minutes from Bradenton Beach

9.0 out of 10, Wonderful, (19)
"Inside was clean and fresh and enough room for all outside needs some cleaning and work on the porch "
Spacious coastal retreat with private yard | Minutes from Bradenton Beach

Beautiful 3 BR pool home minutes from Siesta Key

9.4 out of 10, Exceptional, (9)
"The property was very roomy and had everything we needed. There there is someone that lives on the property but he does not face the property and does not come around. Just know that if you are a skinny Dipper the pool guy shows up unannounced. We enjoyed the place and would stay there again. It's about a 10-minute drive to Siesta Key Beach in 20 minutes drive to Lido beach. Restaurants are not far but you do need to drive as this is in a residential neighborhood. It was very quiet there."
Beautiful 3 BR pool home minutes from 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.
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Other property types in Osprey

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4556)
"Loved the ambiance and close proximity to beach and dining."
The price is SAR 960
SAR 1,169 total
includes taxes & fees
9 Mar - 10 Mar
Tropical Beach Resorts

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (213)
"Very cute and great idea for a place to stay!! Clean and everything was very smooth as far as contact to get in and instructions, definitely would stay again"
The price is SAR 458
SAR 729 total
includes taxes & fees
26 Feb - 27 Feb
Tiny House Siesta

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (290)
"Could be more clean and updated. Great location!"
The price is SAR 961
SAR 1,467 total
includes taxes & fees
24 Feb - 25 Feb
The Ringling Beach House
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.