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Check prices for these dates

Next weekend
16 Jum. I - 18 Jum. I
In two weeks
23 Jum. I - 25 Jum. I
In one month
6 Jum. II - 8 Jum. II
In two months
4 Raj. - 6 Raj.

Compare 3679 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, (230)
"Great stay. Villa was clean and spacious and had everything you need including nice beach gear and beach towels. Beautiful tropical landscaping and nice pool area. Perfect location for walking to shops and restaurants on Venice Ave and short drive or bike ride to beach. Best place to stay in Venice!"
Tropical Villas of Venice Beach
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette
Marina

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

9.8 out of 10, Exceptional, (7)
"This unit was immaculate down to details with a comfortable bed and crystal clear large smart tv. Also, steps from the marina, pool, and dining. "
The price is SAR 371
SAR 707 total
includes taxes & fees
14 May - 15 May
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette
Siesta Key Island Rentals
Room amenity

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (30)
"Great vacation stay "
Siesta Key Island Rentals
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

9.6 out of 10, Exceptional, (45)
"My family and I had such a great stay! The house was the perfect amount of space and had its own beach access. Great place for a family beach getaway"
The price is SAR 1,868
SAR 3,927 total
includes taxes & fees
11 May - 12 May
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, (46)
"Love that it’s a close walk to the beach and Main Street. Will definitely stay here again. "
Close to Beach Access #7, Short Walk to the Village
Private Oasis in Sarasota Florida
Indoor pool

Private Oasis in Sarasota Florida

10.0 out of 10, Exceptional, (33)
"Check in was easy and the back yard was perfect."
Private Oasis in Sarasota Florida
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Smart TV, Netflix, streaming services

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

9.2 out of 10, Wonderful, (15)
"Calm neighborhood super quiet enjoyed my stay"
The price is SAR 296
SAR 825 total
includes taxes & fees
9 May - 10 May
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Private pool House with Fountains & Beach Walkable
Beach nearby

Private pool House with Fountains & Beach Walkable

9.6 out of 10, Exceptional, (173)
"I have stayed at several VRBO's and this house was the cleanest we've ever stayed at! Immaculate was the word I used to my family who live near this property. Everything is updated and had every amenity you could want. I will be staying at this property for all my future visits. Thank you Amy and team!!!"
Private pool House with Fountains & Beach Walkable
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

7.6 out of 10, Good, (9)
"The property was fun but what set this property apart from other stays was the property manager. Excellent communication and was very accomodating to my requests. I even had left something behind at the property and was assisted fully in recovering those items after leaving the property. Exceptional and above expectations!"
The price is SAR 656
SAR 1,859 total
includes taxes & fees
12 May - 13 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
Interior

Siesta Beach Getaway - Minutes to Beach, Shops, Dining

9.4 out of 10, Exceptional, (13)
"Nice decor. Comfortable bedding. Perfect accommodations for our family of three adult couples. Owner’s suite had a spacious shower. Laundry room was equipped with nice washer/dryer. Spacious ranch home in quiet neighborhood. Convenient location. "
Siesta Beach Getaway - Minutes to Beach, Shops, Dining
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!
Outdoor pool, a heated pool

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

9.0 out of 10, Wonderful, (57)
"Great location. Loved being able to bring our doggies! Had everything we needed! Would definitely recommend."
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!
Pineapples House- POOL private SOUTH facing - HOT TUB -close to BEACHES-walkable
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (73)
"The house is i great place to get away and enjoy the beach and house pool and hot tub. Second time staying and definitely would come back. Great host. The only thing I wish was the the pool was a little warmer but we are from Ohioso can be too picky"
Pineapples House- POOL private SOUTH facing - HOT TUB -close to BEACHES-walkable
Private Heated Pool House 6 miles from the Beach
Beach nearby, sun loungers, beach towels

Private Heated Pool House 6 miles from the Beach

9.8 out of 10, Exceptional, (225)
"This house was a pleasant surprise. Extremely clean and well maintained. I plan to return this spring for a longer stay."
Private Heated Pool House 6 miles from the Beach
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, (102)
"We love staying here and keep coming back year after year! Best rental on the key!"
FLASH SALE - Beach & restaurants are OPEN - Fully renovated! Steps to beach.
2-bedroom Spacious townhome in Osprey
Fridge, microwave, oven, stovetop

2-bedroom Spacious townhome in Osprey

10.0 out of 10, Exceptional, (6)
2-bedroom Spacious townhome in Osprey
Family Fun House near Siesta Key
Game room

Family Fun House near Siesta Key

10.0 out of 10, Exceptional, (9)
"Mike was the most thoughtful host and the property and location couldn't have been better. We loved our stay and will certainly be returning next time we’re in Sarasota!"
Family Fun House near Siesta Key
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)
"Friendly guest services!!🤗"
Breezy coastal duplex with private beach access & deck- dog-friendly
4 Bed pool House by Bay! Lido & Siesta Key Beaches very close
Exterior

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

9.8 out of 10, Exceptional, (106)
"This home is in a great location close to the Tamiami Trail. We were able to ride our bikes around the neighborhood and into downtown Sarasota. Our hosts were very responsive and helpful. "
4 Bed pool House by Bay! Lido & Siesta Key Beaches very close
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (11)
"Great Location, convenient to beach and restaurants & shopping.. never drove anywhere in our time at Siesta Key!!"
The price is SAR 1,898
SAR 4,108 total
includes taxes & fees
27 May - 28 May
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village
SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!
Beach nearby

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

9.6 out of 10, Exceptional, (30)
"We had a great time, great location. I would definitely stay again! "
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!
Smart TV, foosball, books

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
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4644)
"Wonderful stay. I enjoy that the resort is so close to the beautiful beach and also local dining and shopping."
The price is SAR 580
SAR 740 total
includes taxes & fees
27 May - 28 May
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, (2123)
"Spacious, clean, affordable and good location for a first trip to Sarasota. "
The price is SAR 564
SAR 638 total
includes taxes & fees
13 May - 14 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.