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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 3695 Vacation Homes in Osprey with updated reviews, rates, and availability.

Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

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
Beach nearby

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
Outdoor pool, a heated pool

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!
Beach nearby, sun loungers

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 AED 1,286
AED 2,803 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.
On the beach, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (99)
"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
Private kitchen

Modern 2 Bedroom Farmhouse

9.2 out of 10, Wonderful, (5)
"Would highly recommend for a one or two night stay"
The price is AED 661
AED 1,535 total
includes taxes & fees
30 Mar - 31 Mar
Modern 2 Bedroom Farmhouse
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
On the beach, sun loungers, beach towels

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 AED 1,829
AED 3,802 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
Beach nearby, sun loungers, beach towels

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

9.8 out of 10, Exceptional, (43)
"Perfectly situated to the beach and the village! Well appointed with all necessities niceties."
Close to Beach Access #7, Short Walk to the Village
Luxury Home w/ Heated Pool and Private Beach Access
Property grounds

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
Terrace/patio

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
Dining

Luxury Family House - Near Coast - Sleeps 14

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property is great overall - lots of space inside and out. We enjoyed the outdoor seating areas, fire pit, and lawn games (Cornhole, ladderball, etc). One disappointment was that the beds did NOT have top sheets. Very strange to us. The pool was very cold so we couldn't make much use of that. But overall it was a great place and location for a friend's weekend. "
The price is AED 1,047
AED 2,933 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
Outdoor dining

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

9.6 out of 10, Exceptional, (84)
"Very nice townhouse with excellent amenities. Located near great restaurants and beaches. Would definitely stay there again."
Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage
Private Oasis in Sarasota Florida
Indoor pool

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
Fridge, microwave, oven, stovetop

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
Bar (on property)

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 AED 312
AED 634 total
includes taxes & fees
1 Apr - 2 Apr
Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill
House in Venice Gardens, Heated Pool, Wi-Fi, Waterfront
Dining

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

9.0 out of 10, Wonderful, (70)
"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
Exterior

Charming Private Suite, Close to Siesta Key, Florida

9.8 out of 10, Exceptional, (43)
"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
Fridge, microwave, oven, stovetop

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."
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
Dining

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

10.0 out of 10, Exceptional, (4)
"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 !!
Beach nearby

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
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4601)
"The room was OK but the bathtub drain was almost clogged. There is a lot of works going on around this property. Basically, it is a standard motel with a pool."
The price is AED 865
AED 1,060 total
includes taxes & fees
31 Mar - 1 Apr
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2105)
"Great little hotel close to the beach, but not so close as to be over-priced. Easy 15 min walk to a public beach access in one direction and 10 min walk to several restaurants/groceries in the other direction. Very clean and updated room with a full size refrigerator and small kitchen. The pool was the best part. Comfortable chairs and never crowded."
The price is AED 711
AED 804 total
includes taxes & fees
2 Apr - 3 Apr
Hibiscus Suites - Gateway to Siesta Key
The Ringling Beach House
Aerial view

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (295)
"We very much enjoyed our stay. Our room was clean and ready for us early. Nancy, the manager, couldn’t have been nicer. This is a no-frills place—but the location can’t be beat! You walk across the street to the beach, and the lively shopping area with restaurants and fun is so close. It’s a quick walk, or you can take the free trolleys/busses. The outdoor area with a nice pool was so relaxing. We used it often. We would stay again. We had 3 teens with us, and they had a blast. We all felt safe....
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.