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Compare 3679 Vacation Homes in Osprey with updated reviews, rates, and availability.

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (224)
"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

Private pool House with Fountains & Beach Walkable

9.6 out of 10, Exceptional, (170)
"Great place for our short visit for my dad’s 80th birthday! Everyone enjoyed the accommodations and the kids loved the pool. We would have loved to stay longer."
Private pool House with Fountains & Beach Walkable

Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts

9.8 out of 10, Exceptional, (109)
"Terrific property with outstanding host/manager. The best appointed and provisioned property ever leased. Very considerate of vacationers and visitors with all amenities in good repair and staples provided. Outstanding experience."
Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts

Tropical Oasis 5 min to Siesta Key, Private Salt Water Pool w Lanai!

10.0 out of 10, Exceptional, (58)
"Our stay at was absolutely wonderful! From the moment we arrived, we felt right at home. The property is even more beautiful in person than in the photos. The space was clean, spacious, and thoughtfully decorated. We loved the cozy ambiance and all the little touches that made it feel like a true retreat. The backyard is a lush wonderland of gorgeous trees and plants, and is fully fenced, so great for dogs. The location is fantastic – quiet, yet close enough to all the attractions we wanted to...
The price is SAR 1,313
SAR 2,847 total
includes taxes & fees
19 Apr - 20 Apr
Tropical Oasis 5 min to Siesta Key, Private Salt Water Pool w Lanai!

FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.

10.0 out of 10, Exceptional, (98)
"Everything was clean & beautiful! Wonderful property manager that reached out to ensure that everything was working properly and we were having a great time! Would definitely stay again!"
FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.

Modern 2 Bedroom Farmhouse

9.2 out of 10, Wonderful, (5)
"Would highly recommend for a one or two night stay"
The price is SAR 675
SAR 1,568 total
includes taxes & fees
31 Mar - 1 Apr
Modern 2 Bedroom Farmhouse

SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

9.8 out of 10, Exceptional, (36)
"We had a wonderful stay. This is truly a very short walk to the beach as well as to the Siesta Key restaurants and shops. We truly enjoyed our stay!"
The price is SAR 2,243
SAR 4,355 total
includes taxes & fees
26 Mar - 27 Mar
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Close to Beach Access #7, Short Walk to the Village

9.8 out of 10, Exceptional, (43)
"The accommodations were actually better than the description. All new appliances, bedding etc. it was all new. Freshly painted and accessories. 3 minute walk to beach. 3 minute walk to Siesta Village restaurants and bars. Highly recommend. "
Close to Beach Access #7, Short Walk to the Village

Luxury Home w/ Heated Pool and Private Beach Access

9.4 out of 10, Exceptional, (97)
"The four of us had a wonderful "Retreat from The Winter" at Miramar! The home, especially the kitchen, was comfortable and well equipped, including many beach chairs. The access to the beach was terrific, with a short walk across the street, through the Aloha Kai gate, and down the private driveway to the white sandy beach. The weather cooperated too, after the one day of rain. The traffic was horrendous, due to a weekday maintenance of the bridge, which was totally out of the hands of the...
Luxury Home w/ Heated Pool and Private Beach Access

Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

7.0 out of 10, Good, (4)
"The home was great, it had everything we needed for our stay. "
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

Luxury Family House - Near Coast - Sleeps 14

2.0 star property
10.0 out of 10, Exceptional, (1)
"A nice big vacation home"
The price is SAR 1,144
SAR 3,091 total
includes taxes & fees
21 Apr - 22 Apr
Luxury Family House - Near Coast - Sleeps 14

Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage

9.6 out of 10, Exceptional, (83)
"We enjoyed our stay and the owners were super helpful and great. Description was just as advertised and close to everything we needed. Would stay here again. Thank you "
Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage

Private Oasis in Sarasota Florida

10.0 out of 10, Exceptional, (26)
"My family and I came down for a weekend stay and the place was perfect for us (2 adults, 3 children ages 3, 9, 13.) We made great use of the backyard pool and lounge area. The location was great for our needs - allowed us to easily get to Siesta Key and up to Ed Smith Stadium for some O's spring training games. The house was exactly as pictured. Check in and out were very easy. "
Private Oasis in Sarasota Florida

Gorgeous Sarasota Private Home with Heated Pool

10.0 out of 10, Exceptional, (28)
"This property is maintained with every consideration in mind. The owners thought of everything - we were very pleased."
Gorgeous Sarasota Private Home with Heated Pool

Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

8.6 out of 10, Excellent, (7)
"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 319
SAR 647 total
includes taxes & fees
16 Apr - 17 Apr
Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

House in Venice Gardens, Heated Pool, Wi-Fi, Waterfront

9.2 out of 10, Wonderful, (69)
"Property was "as advertised. Location was excellent for ease of access to Venice and the surrounding area. Bird life was especially good for viewing in the back yard and we had at least 3 small alligators in the lake. Interior of the house was clean but could use some further maintenance (eg not all the blinds are in good repair.). Host was responsive and easy to work with."
House in Venice Gardens, Heated Pool, Wi-Fi, Waterfront

Charming Private Suite, Close to Siesta Key, Florida

9.8 out of 10, Exceptional, (42)
"The property was clean and cozy. It had all the things we needed and worked great for the few days we were in Sarasota to visit friends. We hope to stay here again on our next visit. "
Charming Private Suite, Close to Siesta Key, Florida

Breezy coastal duplex with private beach access & deck- dog-friendly

9.0 out of 10, Wonderful, (8)
"We had a lovely time.. needs to be updated. Area rug was very dirty.. could use some small upgrades. Kitchen well equipped."
The price is SAR 784
SAR 1,973 total
includes taxes & fees
22 Mar - 23 Mar
Breezy coastal duplex with private beach access & deck- dog-friendly

3bed house with pool in lovely West of Trail Sarasota. Big yard, central AC&WiFi

10.0 out of 10, Exceptional, (3)
"Nice property. Owners new to Vrbo with this property and really want to make it great. Good communication. Had a few hiccups with cleanliness as we first got in and pool condition but the owners got right on it to make it right. Neighborhood is fantastic. I do the living room could use some extra seating in the living room for a larger family stay. Maybe a loveseat or another sofa . Pool was nice but note that the whirlpool spa pictured is not working as a spa and is same temp as pool and no...
3bed house with pool in lovely West of Trail Sarasota. Big yard, central AC&WiFi

SKV 311 - Pool, Walk to Village, Beach, Bars, Restaurants !!

9.4 out of 10, Exceptional, (29)
"Great location, and we love the beach."
SKV 311 - Pool, Walk to Village, Beach, Bars, 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, (4596)
"Brandy at front desk is the best. Outstanding service"
The price is SAR 960
SAR 1,169 total
includes taxes & fees
30 Mar - 31 Mar
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2104)
"Friendly, great location. Clean and good value"
The price is SAR 772
SAR 872 total
includes taxes & fees
1 Apr - 2 Apr
Hibiscus Suites - Gateway to Siesta Key

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (239)
"This place was big enough to fit my family of 5, comfortably. Staff was amazing and check in and out was easy! Will stay again! "
The price is SAR 338
SAR 593 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.