A marina with docked boats, a wooden bridge, and a building with a red roof.

Search Vacation Homes in Osprey

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Osprey vacation homes

Hair dryer, towels, soap, shampoo

Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.6 out of 10, Exceptional, (4 reviews)
"The house was very clean and well accommodating. There was room for our boat in the driveway. Will definitely stay again if in the area."
United States
Jeremy
The price is ￥14,406
￥45,795 total
includes taxes & fees
Jul 13 - Jul 14
Path to Paradise.
Sun loungers

Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (3 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is ￥10,913
￥37,834 total
includes taxes & fees
Aug 11 - Aug 12
Charming 2-bedroom house in Englewood with WiFi and AC
Dining

Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is ￥17,146
￥39,907 total
includes taxes & fees
Aug 11 - Aug 12
Lakeview Bradenton Rental Near Beaches & IMG
Microwave, oven, stovetop

Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
9.2 out of 10, Wonderful, (32 reviews)
"What a lovely find! Yani’s place is cute, clean, and perfectly located. We had a fantastic stay and appreciated the hospitality. We’ll definitely be back—highly recommend!"
United States
Jani S.
The price is ￥13,824
￥33,956 total
includes taxes & fees
Jul 15 - Jul 16
Charming 2-bedroom house in lovely Sarasota with yard.
Living area

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
The price is ￥13,922
￥35,712 total
includes taxes & fees
Jul 13 - Jul 14
Nestled in North Port. Updated 2 Bed / 1 Bath.
TV

Lemon Bay Hideaway, Retro Beach Bungalow

Lemon Bay Hideaway, Retro Beach Bungalow
South Venice
10.0 out of 10, Exceptional, (12 reviews)
"Good location, very clean Thanks"
United States
Randy R.
The price is ￥12,213
￥48,045 total
includes taxes & fees
Jul 13 - Jul 14
Lemon Bay Hideaway, Retro Beach Bungalow
Beach nearby, sun loungers, beach towels

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Ridge Wood Heights
10.0 out of 10, Exceptional, (17 reviews)
"Great place. Clean with everything you need"
United States
Thomas Lee
The price is ￥19,644
￥53,920 total
includes taxes & fees
Jul 13 - Jul 14
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Property grounds

The Ashton Hideaway

The Ashton Hideaway
2.0 star property
Sarasota
The price is ￥14,320
￥44,504 total
includes taxes & fees
Jul 13 - Jul 14
The Ashton Hideaway
Beach nearby, sun loungers, beach towels

Home in quiet Bird Sanctuary Neighborhood, close to Beach

Home in quiet Bird Sanctuary Neighborhood, close to Beach
South Venice
9.6 out of 10, Exceptional, (19 reviews)
"Good location for us"
United States
EdgefieldFarm
The price is ￥14,551
￥50,040 total
includes taxes & fees
Jul 15 - Jul 16
Home in quiet Bird Sanctuary Neighborhood, close to Beach
Fridge, microwave, oven, stovetop

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (79 reviews)
"Her stay was outstanding everything was so professionally ready for us we felt at home comfortable the Privacy was impeccable"
United States
James W.
The price is ￥14,406
￥43,644 total
includes taxes & fees
Jul 23 - Jul 24
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Terrace/patio

Sunshine Hideaway 6 mins to Warm Mineral Springs

Sunshine Hideaway 6 mins to Warm Mineral Springs
North Port
10.0 out of 10, Exceptional, (9 reviews)
"Very nice place with comfortable beds "
United States
Josh H.
The price is ￥16,976
￥41,980 total
includes taxes & fees
Jul 13 - Jul 14
Sunshine Hideaway 6 mins to Warm Mineral Springs
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is ￥16,157
￥50,778 total
includes taxes & fees
Jul 13 - Jul 14
Siesta Heron Suites & Villas
Beach nearby, beach towels

Nautical Nook

Nautical Nook
Englewood
10.0 out of 10, Exceptional, (8 reviews)
"Stayed here several times. Always perfect. Feels like home. "
United States
christine w.
The price is ￥16,896
￥41,399 total
includes taxes & fees
Jul 15 - Jul 16
Nautical Nook
Interior

Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.
Sarasota Springs
The price is ￥7,421
￥18,926 total
includes taxes & fees
Jul 19 - Jul 20
Cozy 1-bedroom private room in Sarasota.
2 bedrooms, iron/ironing board, WiFi, bed sheets

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (31 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is ￥18,152
￥53,856 total
includes taxes & fees
Jul 13 - Jul 14
[escape to paradise] siesta key beach getaway
Fridge, microwave, oven, stovetop

3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport

3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport
Siesta Key
9.0 out of 10, Wonderful, (31 reviews)
"Perfect spot to stay near Siesta Key village, would definitely stay here again! "
United States
Dale R.
The price is ￥27,348
￥55,294 total
includes taxes & fees
Jul 20 - Jul 21
3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport
Fridge, microwave, oven, stovetop

Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota

Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota
Sarasota
9.8 out of 10, Exceptional, (7 reviews)
"This was a great stay for us. It was extremely clean and just as described."
United States
Kenzie Q.
The price is ￥20,695
￥57,257 total
includes taxes & fees
Jul 16 - Jul 17
Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota
Sun loungers, beach towels

Spacious Updated 7 Min to Beach. Loaded w/amenities Private and fenced yard PETS

Spacious Updated 7 Min to Beach. Loaded w/amenities Private and fenced yard PETS
South Venice
9.4 out of 10, Exceptional, (23 reviews)
"Family friendly. Plenty of space. Exactly what we needed. "
United States
Andréa H.
The price is ￥16,168
￥53,301 total
includes taxes & fees
Jul 27 - Jul 28
Spacious Updated 7 Min to Beach. Loaded w/amenities Private and fenced yard PETS
Dining

Sunny 3BR Oasis • Water View • Beach Gear • Fully Fenced Yard • Near Siesta Key

Sunny 3BR Oasis • Water View • Beach Gear • Fully Fenced Yard • Near Siesta Key
Sarasota Springs
10.0 out of 10, Exceptional, (10 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
The price is ￥16,734
￥58,425 total
includes taxes & fees
Jul 13 - Jul 14
Sunny 3BR Oasis • Water View • Beach Gear • Fully Fenced Yard • Near Siesta Key
Fridge, microwave, oven, stovetop

10 minutes to Mineral Springs w/large Pool and Pet Friendly!

10 minutes to Mineral Springs w/large Pool and Pet Friendly!
North Port
9.6 out of 10, Exceptional, (14 reviews)
"This house was phenomenal!! We were so happy there were spices in the kitchen for us to be able to cook dinner our first night there! We had a great time. Convenient location to do multiple areas for activities!"
United States
Madeline W.
The price is ￥18,189
￥64,046 total
includes taxes & fees
Jul 17 - Jul 18
10 minutes to Mineral Springs w/large Pool and Pet Friendly!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"Old Florida style motel property. All staff was extremely helpful and friendly. Adjacent tiki bar was a good time. Great place to unwind after a hot summer day. Live music on Friday night was nice addition. Not fancy, but clean and comfortable for a great price!"
Shari 1-night trip
Posted less than an hour ago
Golden Host Resort - Sarasota

Find out more about Osprey

Osprey Vacation Homes information

Number of reviews
276
Accommodation
4087 Vacation Homes
Lowest Price
￥18,926
Highest Price
￥64,046