Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

Holiday Home in Bay Acres

2.0 star property
The price is AU$545
includes taxes & fees
8 Dec - 9 Dec
Charming Osprey Home

Holiday Home in North Port

10.0 out of 10, Exceptional, (12)
"Very cute and cozy home in North Port FL close to shops and not a far drive to the beach. "
United States
James Y.
Nestled in North Port. Updated 2 Bed / 1 Bath.

Holiday Home in South Venice

10.0 out of 10, Exceptional, (42)
"We had a wonderful time! The house was perfect and such a great location."
United States
Kellee N.
The price is AU$527
includes taxes & fees
16 Dec - 17 Dec
8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear

Holiday Home in Siesta Key

3.0 star property
9.6 out of 10, Exceptional, (50)
"Very nice place, we loved it. Great location. "
United States
Derrick
The price is AU$436
includes taxes & fees
3 Dec - 4 Dec
Siesta Key Island Rentals

Holiday Home in Manasota Key

8.4 out of 10, Very good, (12)
"Great place to stay. "
United States
Scott
The price is AU$579
includes taxes & fees
1 Dec - 2 Dec
Coastal duplex with private beach access & deck - dog-friendly

Holiday Home in Sarasota Springs

9.6 out of 10, Exceptional, (25)
"Such a nice place!!!! And the sweetest hostess! Hope it’s available next time I’m in town. "
United States
Tricia L.
Peaceful Room 15 Minutes from Downtown or Beach

Holiday Home in Olde Englewood Village

9.8 out of 10, Exceptional, (60)
"Very good, great location 👍👍"
United States
James M.
The price is AU$394
includes taxes & fees
26 Nov - 27 Nov
Old Floridian cottage in Historic Gulf Village

Holiday Home in North Port

10.0 out of 10, Exceptional, (16)
"Had an awesome with friends and family and will stay again if we’re in the area."
United States
Eric H.
The price is AU$714
includes taxes & fees
29 Nov - 30 Nov
New Two story Cozy House Near Warm Mineral Springs

Holiday Home in Siesta Key

3.5 star property
8.4 out of 10, Very good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is AU$538
includes taxes & fees
10 Dec - 11 Dec
Siesta Heron Suites & Villas

Holiday Home in Englewood South

The price is AU$475
includes taxes & fees
26 Nov - 27 Nov
Charming 2-bedroom house in Englewood with WiFi and AC

Holiday Home in Sarasota

9.4 out of 10, Exceptional, (16)
"Great location! Clean, easy to find and perfect amount of room. "
United States
Maribeliz G.
The price is AU$343
includes taxes & fees
8 Dec - 9 Dec
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Holiday Home in Siesta Key

9.8 out of 10, Exceptional, (25)
"The property was very clean and conveniently located ."
United States
David
The price is AU$450
includes taxes & fees
1 Dec - 2 Dec
[lounge like locals] walk to siesta beach +bikes

Holiday Home in South Venice

9.6 out of 10, Exceptional, (26)
"Great location and safe neighborhood. Definitely will stay again if available."
United States
Luis M.
Stylish house minutes from the beach

Holiday Home in Southgate

10.0 out of 10, Exceptional, (4)
"We loved the retro decor of the home, the comfy beds, and the great location! We loved being close to downtown Sarasota and to all the activities we attended! "
United States
Merita S.
The price is AU$538
includes taxes & fees
1 Dec - 2 Dec
Retro-Inspired Stay, BBQ Patio, Close to Downtown

Holiday Home in The Meadows

10.0 out of 10, Exceptional, (18)
"Fun place "
United States
Maureen
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Holiday Home in Sabal Harbour

2.0 star property
10.0 out of 10, Exceptional, (19)
"Everything was great!"
United States
Lisa and Colin M.
The price is AU$534
includes taxes & fees
29 Nov - 30 Nov
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Holiday Home in Venice

9.8 out of 10, Exceptional, (18)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is AU$718
includes taxes & fees
26 Nov - 27 Nov
Myakka River

Holiday Home in Sarasota Springs

9.8 out of 10, Exceptional, (27)
"The house was great and everything was well equipped. The area is nice and the famous beaches are just a short drive away. I fully recommend this house although it was a bit pricey during our stay"
Germany
Alina L.
The price is AU$440
includes taxes & fees
9 Dec - 10 Dec
Coastal Pool Bungalow - 15 Mins to Famous Beaches

Holiday Home in Alta Vista

9.8 out of 10, Exceptional, (63)
"extremely comforting and accommodating for me and my friends. "
United States
Carolina V.
The price is AU$488
includes taxes & fees
7 Dec - 8 Dec
Luxury Family Home Near Downtown & Siesta Key Beach

Holiday Home in Englewood

10.0 out of 10, Exceptional, (46)
"Very well maintained. Host was super responsive from booking to check out. On time, on budget and very accommodating. Highly recommended "
United States
Ernest C.
The price is AU$543
includes taxes & fees
26 Nov - 27 Nov
Waterfront Getaway, a Boating Paradise
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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Top Osprey Hotel Reviews

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Osprey Holiday Homes information

Number of reviews
503
Accommodation
3899 Holiday Homes
Lowest Price
AU$347
Highest Price
AU$718

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