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Compare 3697 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, (227)
"Amazing 3 day get away. The best place to stay in Venice! "
Tropical Villas of Venice Beach

New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette

9.8 out of 10, Exceptional, (7)
"Everything was above expectations. We have a great time at this facilities, clean and nice room . Relax …."
The price is AED 364
AED 692 total
includes taxes & fees
7 May - 8 May
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette

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

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

9.6 out of 10, Exceptional, (43)
"We celebrated my birthday at this home and everyone had a nice time. We loved that you can see the ocean from every room on that side of the house."
The price is AED 2,564
AED 4,723 total
includes taxes & fees
27 Apr - 28 Apr
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, (45)
"The property was very clean and the check in process was incredibly easy. Just a couple minor issues like some wall outlets not working and the shower/bathtub not draining very well. They provided us with beach towels, beach chairs and umbrellas. Close to the beach, shops and dining. Would recommend for couples and families. "
The price is AED 731
AED 1,999 total
includes taxes & fees
2 May - 3 May
Close to Beach Access #7, Short Walk to the Village

Private Oasis in Sarasota Florida

10.0 out of 10, Exceptional, (31)
"We were looking for somewhere to stay for a few days before flying back to UK from Tampa. This house was ideal as it was equally distant from both Siesta Key and Armand Circle with the restaurants and bars and just a short Uber ride.The house was really well equipped and the neighbourhood is lovely and quiet for chilled pool days.Lovely stay and lovely hosts "
Private Oasis in Sarasota Florida

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

9.2 out of 10, Wonderful, (13)
"Great location! Clean, easy to find and perfect amount of room. "
The price is AED 290
AED 808 total
includes taxes & fees
4 May - 5 May
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Private pool House with Fountains & Beach Walkable

9.6 out of 10, Exceptional, (172)
"Great location. Beach couple blocks away-walkable which is a plus for us. During spring break traffic is heavy so we can walk to beach or historic downtown or to local restaurants.Rented e-bikes for a few days and explored."
Private pool House with Fountains & Beach Walkable

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

6.8 out of 10, (6)
"Property was clean, larger than expected and host was very accommodating and responsive. "
The price is AED 643
AED 1,802 total
includes taxes & fees
14 May - 15 May
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

Siesta Beach Getaway - Minutes to Beach, Shops, Dining

9.6 out of 10, Exceptional, (12)
"We were impressed with the property. Neighbors were even nice! Not on the beach, so that was a bit of a drive, especially with traffic. But stores were nearby and the neighborhood seemed decent. Would stay here again. "
Siesta Beach Getaway - Minutes to Beach, Shops, Dining

Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!

9.0 out of 10, Wonderful, (57)
"The pool was not very clean. No lights in the BBQ area and pool area. No gas for BBQ , we have to buy it. "
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!

Pineapples House- POOL private SOUTH facing - HOT TUB -close to BEACHES-walkable

10.0 out of 10, Exceptional, (71)
"My husband and 3 teenagers had the best time. The house is exactly as described. It’s a beautiful home, inside and out. It is fully stocked with everything you would need and was very clean!! The host was very accommodating and helpful. Beaches, shopping, restaurants and fishing are all a short drive away. "
Pineapples House- POOL private SOUTH facing - HOT TUB -close to BEACHES-walkable

Private Heated Pool House 6 miles from the Beach

9.8 out of 10, Exceptional, (224)
"The cleanliness of the home and outdoor space was emaculate. We loved the pool. However there are a couple things in the home that could be upgraded. The mattresses were old and need replaced. The pillows could use a refresh too. But the host provided everything needed and more. 6 miles to beach doesn't sound far but it could take 10 minutes or 30 minutes depending on when you head to the beach. Traffic can be backed up for miles. Other than that no complaints. "
Private Heated Pool House 6 miles from the Beach

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

10.0 out of 10, Exceptional, (101)
"Absolutely beautiful beach home. Fantastic layout for sharing with friends or family. Very quiet stretch of beach just a few steps away, close enough for a baby monitor during nap time (we had a one year old in our party)! Also a short walk to the bars and restaurants. Fantastic sunsets! Super friendly and responsive host/owner, and that special feel of actually staying in someone’s home that they use vs. just a pure vacation rental."
FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.

2-bedroom Spacious townhome in Osprey

10.0 out of 10, Exceptional, (6)
"property was immaculate, Host was very helpful, an excellent shower, beds very comfortable, location quiet and secluded.will stay again when in Osprey."
2-bedroom Spacious townhome in Osprey

Family Fun House near Siesta Key

10.0 out of 10, Exceptional, (8)
"longtime friends went for a week of golf to Sarasota. We were fortunate to find this property as it gave everybody their own bedroom own bathroom plenty of space to relax. Also, after our long days of golf, the pool was refreshing cleaned twice a week."
Family Fun House near Siesta Key

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

4 Bed pool House by Bay! Lido & Siesta Key Beaches very close

9.8 out of 10, Exceptional, (104)
"Good location to be close to airport and short drive to beaches. There’s lots to do in the area! We were a little frustrated when we arrived the pool was low on water so the pump had not been running. Had to have pool people and electricians there and didn’t get fixed until our last day. Pool guys did not do anything to clean besides dump chemicals so my husband was cleaning it and filling it with a garden hose so our kids could at least float in it. "
4 Bed pool House by Bay! Lido & Siesta Key Beaches very close

Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

9.6 out of 10, Exceptional, (10)
"We loved the house and the location was perfect! "
The price is AED 1,294
AED 3,352 total
includes taxes & fees
22 May - 23 May
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!

9.6 out of 10, Exceptional, (29)
"Clean and very close to village."
The price is AED 1,095
AED 2,343 total
includes taxes & fees
28 Apr - 29 Apr
SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!
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

Huge Pool, Close to Beaches, Restaurants, Shopping & More!

9.6 out of 10, Exceptional, (22)
"What a wonderful place to relax! Will definitely recommend to family and friends and even come back to stay!"
Huge Pool, Close to Beaches, Restaurants, Shopping & More!

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4641)
"Clean, new and good price. Beach close. restaurants within walking distance. Staff very nice and eager to please. No complaints at all !"
The price is AED 538
AED 691 total
includes taxes & fees
27 May - 28 May
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2117)
"Lovely well-appointed apartment with separate bedroom and a sitting room/kitchen. Everything you needed to cook your own food (small induction hob and a combination oven/microwave, pots etc). We only had 3 forks on arrival but quickly rectified. Despite being situated on a main road and our room being roadside, it was nice and quiet inside. Only downside was the pool being situated right next to the road - though it does get the sun for the longest there. "
The price is AED 553
AED 625 total
includes taxes & fees
1 May - 2 May
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.