Vacation Rentals & House Rentals in Osprey

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Fireplace
Wireless Internet
Air conditioning
Swimming pool

Private pool
Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
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Internet access
DVD player
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Cot available
Sea view
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Shared outdoor pool (unheated)
Shared indoor pool
Private outdoor pool (heated)
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Pool or snooker table
Cribs
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Shared outdoor pool (heated)
Swing set or jungle gym
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Iron
Hair dryer
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Freezer
Linen provided
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Bicycles available
Climbing frame
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Staffed property
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Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
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Non-Smoking property
Smoking - Ask
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Skiing – property near ski resort
Walking trips
Tennis in town
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Golf course on site or within 15 min walk
Golf within 30mins drive
Waterfront

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31 Houses

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Dunmore

Osprey house

3 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$218

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$161

Great rentals within 20 miles that match your search

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

2 bedrooms
4 bathrooms

sleeps 6

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$430

Sunset Point Siesta Key FL AWESOME RENTAL !!

Siesta Key villa

2 bedrooms
2 bathrooms

sleeps 4

“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!

Responds fast! avg. 3 hours 50 minutes

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Price per night from

$802

Sandy Toes Town Home

Siesta Key townhouse

3 bedrooms
3 bathrooms

sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

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Price per night from

$272

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

3 bedrooms
2 bathrooms

sleeps 6

“Location location” Great house convincent , clean , close to everything

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Price per night from

$121

Quiet pool home with lake view, close to beaches

Venice house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$229

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$295

Perfect Venice Island 2+2 Vacation Rental close to downtown and the beach!

Venice house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$132

The Siesta Studio

Sarasota studio

Studio
1 bathroom

sleeps 2

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Price per night from

$155

Peaceful, Private, Paradise in Englewood. House with heated pool

Englewood house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$258

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$745

Vacation Rental Boutique Suite Windmills

Englewood private room

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$224

Beautiful Florida Home

Venice house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$249

5 min to the Beach, Sleeps 6

Nokomis house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$137

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$1,030

LEMON BAY COTTAGE

Englewood house

3 bedrooms
2 bathrooms

sleeps 6

“Perfect family cottage in Lemon Bay” Such a great little house and surprisingly bigger than pictures reveal. Perfect for a family with kids. 3rd toilet tucked away in laundry shed for easy access from pool. Great location as well, close to beaches, parks and many restaurants within walking distance. Definitely will rent there again. House was fresh, clean and inviting.

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$103