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

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Check prices for these dates

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

Our top choices for Osprey holiday 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 £214
includes taxes & fees
13 Jul - 14 Jul
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 £180
includes taxes & fees
25 Jul - 26 Jul
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 £185
includes taxes & fees
11 Aug - 12 Aug
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)
"Great home with a wonderful back yard and very welcoming for pets. Very comfortable , great shower. I would stay here again!"
United States
Anonymous traveller
The price is £160
includes taxes & fees
15 Jul - 16 Jul
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 £169
includes taxes & fees
13 Jul - 14 Jul
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 £225
includes taxes & fees
13 Jul - 14 Jul
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 £247
includes taxes & fees
13 Jul - 14 Jul
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 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 £235
includes taxes & fees
15 Jul - 16 Jul
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 £206
includes taxes & fees
23 Jul - 24 Jul
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 £196
includes taxes & fees
13 Jul - 14 Jul
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 £242
includes taxes & fees
13 Jul - 14 Jul
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 £196
includes taxes & fees
13 Jul - 14 Jul
Nautical Nook
Interior

Cozy 1-bedroom private room in Sarasota.

Cozy 1-bedroom private room in Sarasota.
Sarasota Springs
The price is £57
includes taxes & fees
9 Aug - 10 Aug
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 £249
includes taxes & fees
13 Jul - 14 Jul
[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 £255
includes taxes & fees
14 Jul - 15 Jul
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 £263
includes taxes & fees
16 Jul - 17 Jul
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.
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 £269
includes taxes & fees
13 Jul - 14 Jul
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 £297
includes taxes & fees
17 Jul - 18 Jul
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.
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Top Osprey Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

8/10 Good
"Staff was friendly. Very helpful. Resort was in a great location. Less than a 3 minute walk to a private beach. A very nice tropical pool oasis was right across from where we were located. We were within walking distance of restaurants and beach shops. The rooms were a little dated but very clean. A little smaller than what we are used too but it was very cozy. We would stay there again."
Christy 5-night trip
Posted 4 hours ago
Tropical Beach Resorts

Find out more about Osprey

Osprey Holiday Homes information

Number of reviews
276
Accommodation
4065 Holiday Homes
Lowest Price
£57
Highest Price
£297