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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 3697 Vacation Homes in Osprey with updated reviews, rates, and availability.

Siesta Key Island Rentals
Room amenity

Siesta Key Island Rentals

3.0 star property
9.8 out of 10, Exceptional, (33)
"Great vacation stay "
The price is AED 767
AED 1,533 total
includes taxes & fees
8 Jun - 9 Jun
Siesta Key Island Rentals
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, (233)
"The property was in a quiet area and was very pleasant and comfortable. "
Tropical Villas of Venice Beach
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very Good, (31)
"Just want to provide a few words of advice to future guests: Although there is a coffee maker, its a Keurig so you'll need to buy kcups (we brought ground coffee). Minor issue: you may also need to BYO salt and pepper shakers, but perhaps by the time you are reading this previous guests will have left them behind. To be fair, the list of "what to bring" is clear that nothing is provided, so it might be best to check-in first, then go grocery shopping! "
The price is AED 445
AED 1,242 total
includes taxes & fees
6 Jun - 7 Jun
Siesta Heron Suites & Villas
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Beach nearby, sun loungers, beach towels

Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

9.6 out of 10, Exceptional, (102)
"Beautiful property! Host was exceptional. Loved our time here! "
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Casa Azul 2Bed/1Bath
Terrace/patio

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (60)
"Very comfortable and perfect location to the airport! "
The price is AED 331
AED 717 total
includes taxes & fees
22 Jun - 23 Jun
Casa Azul 2Bed/1Bath
GORGEOUS 3 Bedroom/2 Bath Home NEAR SIESTA KEY!
Fridge, microwave, oven, stovetop

GORGEOUS 3 Bedroom/2 Bath Home NEAR SIESTA KEY!

9.8 out of 10, Exceptional, (13)
"Our family stayed here for vacation and the property was great! Clean with a beautiful pool."
GORGEOUS 3 Bedroom/2 Bath Home NEAR SIESTA KEY!
Beachfront estate near Sarasota with spectacular gulf views
A heated pool

Beachfront estate near Sarasota with spectacular gulf views

8.8 out of 10, Excellent, (19)
"The house was beautiful and having the beach on one side and the bay on the other was amazing! Perfect vacation home! Absolutely gorgeous!"
Beachfront estate near Sarasota with spectacular gulf views
Comfy private home In Venice, Florida - Heated Pool, Minutes From the Beach
Beach nearby, sun loungers, beach towels

Comfy private home In Venice, Florida - Heated Pool, Minutes From the Beach

9.8 out of 10, Exceptional, (145)
"Wonderful home and host. Just minutes from beaches. Great time had by all. "
Comfy private home In Venice, Florida - Heated Pool, Minutes From the Beach
All-New, Huge Pool, 70" TV, Bunk Beds, Tiki Bar & Grill!
Outdoor pool, a heated pool

All-New, Huge Pool, 70" TV, Bunk Beds, Tiki Bar & Grill!

8.8 out of 10, Excellent, (15)
"I booked this place with my 3 children and husband. The set up is nice and it was perfect for our family. We will definitely come back soon."
The price is AED 364
AED 729 total
includes taxes & fees
6 Jun - 7 Jun
All-New, Huge Pool, 70" TV, Bunk Beds, Tiki Bar & Grill!
Updated and Spacious, Minutes to Siesta Key and Downtown Sarasota, 2 Game Rooms
A heated pool

Updated and Spacious, Minutes to Siesta Key and Downtown Sarasota, 2 Game Rooms

10.0 out of 10, Exceptional, (8)
"Absolutely wonderful place to stay in the area. Check in was so smooth, and the hosts were so accommodating when it came to getting us into the home before the bad weather. Would absolutely stay here again!"
Updated and Spacious, Minutes to Siesta Key and Downtown Sarasota, 2 Game Rooms
Beautiful 3 BR pool home minutes from Siesta Key - Blue Dolphin
Fridge, microwave, oven, stovetop

Beautiful 3 BR pool home minutes from Siesta Key - Blue Dolphin

9.2 out of 10, Wonderful, (17)
"Safe, plenty of kitchen utensils, and excellent communication with the rental company. Everything was excellent, especially the location of the property."
Beautiful 3 BR pool home minutes from Siesta Key - Blue Dolphin
1.3 Acres PETS Waterfront FUN! Caged/Heated Pool, 100' Pier, CANOES Kayaks incl!
A heated pool

1.3 Acres PETS Waterfront FUN! Caged/Heated Pool, 100' Pier, CANOES Kayaks incl!

9.4 out of 10, Exceptional, (80)
"For a mini vacation you can't ask for more. It's a short drive to several beaches and has a pool. To top it off they offer use of there kayaks to use right off the dock!"
The price is AED 731
AED 1,670 total
includes taxes & fees
29 Jun - 30 Jun
1.3 Acres PETS Waterfront FUN! Caged/Heated Pool, 100' Pier, CANOES Kayaks incl!
Newly Renovated Large 4BR w/ Pool - Walk to Gated beach
Beach nearby, sun loungers, beach towels

Newly Renovated Large 4BR w/ Pool - Walk to Gated beach

9.4 out of 10, Exceptional, (35)
"This property is excellent!"
Newly Renovated Large 4BR w/ Pool - Walk to Gated beach
Oceanfront home
Outdoor pool, a heated pool

Oceanfront home

9.6 out of 10, Exceptional, (77)
"Sitting at the dock in the late evening was beautiful!"
Oceanfront home
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, (10)
"The home was great, it had everything we needed for our stay. "
The price is AED 578
AED 1,722 total
includes taxes & fees
6 Jun - 7 Jun
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches
WATERFRONT STUDIO UNIT 107 at the Ramada Inn Sara Bay Marina 7150 N Tamiami Tr
Beach

WATERFRONT STUDIO UNIT 107 at the Ramada Inn Sara Bay Marina 7150 N Tamiami Tr

8.0 out of 10, Very Good, (132)
"Very nice trip. Hope to go back there again."
WATERFRONT STUDIO UNIT 107 at the Ramada Inn Sara Bay Marina 7150 N Tamiami Tr
Walk to Beach: Pet-Friendly Oasis on Manasota Key!
Beach nearby, beach umbrellas

Walk to Beach: Pet-Friendly Oasis on Manasota Key!

2.5 star property
10.0 out of 10, Exceptional, (22)
"Thanks!"
Walk to Beach: Pet-Friendly Oasis on Manasota Key!
Casey Key Oasis 3BR home on .75 acre w heated pool, boat dock, beach access
Beach nearby, sun loungers, beach towels

Casey Key Oasis 3BR home on .75 acre w heated pool, boat dock, beach access

9.8 out of 10, Exceptional, (24)
"Very convenient everything is close Large pool and back yard"
Casey Key Oasis 3BR home on .75 acre w heated pool, boat dock, beach access
3 miles to beach, hot tub & fenced yard for pup
Outdoor dining

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

9.8 out of 10, Exceptional, (17)
"Wife and I enjoyed the place very much."
3 miles to beach, hot tub & fenced yard for pup
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)
"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 3,262
AED 5,604 total
includes taxes & fees
8 Jun - 9 Jun
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
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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