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Air conditioning
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Private pool

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Private indoor pool
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Jacuzzi or hot tub
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Cot available
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Private outdoor pool (unheated)
Private outdoor pool (heated)
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Staffed property
Private fishing lake or river
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Linen provided
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Housekeeping Included

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Pets allowed
Parking
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Smoking allowed
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Golf course on site or within 15 min walk
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1,183 Houses

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Dunmore

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$191

Sunny Oasis w/ New Appliances & Furnishings - Near Coast, Dining

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$171

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$282

2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key

Osprey condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$79

2Bedroom Beach Cottage - 3 Miles to Siesta Key

Osprey cottage

2 bedrooms / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 57 minutes

Price per night from

$98

CKBH (Casey Key Beach House)

Osprey house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$583

Tranquil Sarasota Home < 1 Mile to Boat Launch!

Osprey house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$83

Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key

Osprey condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$153

New Executive Listing. Heated Pool, Dog Friendly, Kayak Launch & Park, Private S

Osprey house

3 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 3 minutes

Price per night from

$185

Great rentals within 20 miles that match your search

Beautiful 2 bedroom 2 bath in Palm Aire Country Club near fabulous beaches

Sarasota condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$114

Park Model with lanai, large deck, block from pool

Venice house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$138

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 17 minutes

Price per night from

$141

Tropical retreat with pool and gardens in the heart of Sarasota

Sarasota house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$240

Palm Bay Club - 100 Yards From The Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$275

Charming Private Studio in Historic Downtown Area

Sarasota studio

Studio / 1 bathroom / sleeps 3

Responds fast! avg. 17 minutes

Price per night from

$130

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$381

Addy's Villas: 2BR

Nokomis villa

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$222

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$656

One Bedroom in Historic Burns Square District downtown

Sarasota apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 17 minutes

Price per night from

$150

Castel del Mare, Luxury Condo, Near Siesta Key

Sarasota condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$112

March 21-28, 2020 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$787

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$337

It's Not Too Late! 2B/2B Condo available for season at the Plantation G & CC

Venice condo

2 bedrooms / 2 bathrooms / sleeps 3

Price per night from

$132

Piece of Paradise

Sarasota condo

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Price per night from

$109

Downtown Apartment in Historic Burns Square downtown Sarasota

Sarasota apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 17 minutes

Price per night from

$150

Sarasota! 6 miles from world rowing at Benderson, rare opportunity

Fruitville house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$394

LAKEFRONT,POOL,WALK TO BEACH, FREE KAYAKS,BICYCLES

Nokomis house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$125

Rare Beach to Bay Condo

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$193

Your perfect vacation starts here !

Casey Key villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$256

Sarasota River House Paradise. 4BR. Free kayaks, bikes, fishing, hot tub + more.

Sarasota house

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$407

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,144

Siesta Key Condo

Siesta Key condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$147

Venice Island on BEACH 8th flr near Siesta Key

Venice apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$203

Warm Mineral Spring Vacation Home

Warm Mineral Springs house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$91

Tropical Dreams Sarasota - Close to Siesta Key, Updated Villa Avail Feb Mar Apr

Sarasota house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 32 minutes

Price per night from

$240

Tropical Dreams Sarasota -Updated, Near Siesta Key, Lg patio King beds Unit #2

Sarasota apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 32 minutes

Price per night from

$240

Tropical Dreams Sarasota - New tile & granite New king beds Near Siesta Key #3

Sarasota apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 32 minutes

Price per night from

$240

Tropical Dreams Sarasota - Updated 2 Br 2 King beds, Near Siesta Key villa # 4

Sarasota apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 32 minutes

Price per night from

$240

Viewing 38 of 1,183
rentals in Osprey

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COVID-19 Update

Osprey Rentals

Per night

1,183 Houses

Viewing 38 of 1,183rentals in Osprey

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Viewing 38 of 1,183
rentals in Osprey