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Jacuzzi or hot tub
Wireless Internet
Air conditioning
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Private pool
Heated pool
Private indoor pool
Balcony or terrace
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DVD player
Grill
Fireplace
Cot available
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Dishwasher
Children's pool
Shared outdoor pool (unheated)
Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
Pool or snooker table
Cribs
Ceiling Fans
Clothes dryer
Games room
Table tennis
Shared outdoor pool (heated)
Swing set or jungle gym
Fax machine
Microwave
Toaster
Iron
Hair dryer
Stove
Fridge
Freezer
Linen provided
Video player
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
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Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
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Skiing – property near ski resort
Walking trips
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Golf course on site or within 15 min walk
Golf within 30mins drive
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107 Houses in Osprey with hot tubs

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LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms
2 bathrooms

sleeps 6

Match: Jacuzzi or hot tub

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Price per night from

$161

Great rentals within 20 miles that match your search

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Jacuzzi or hot tub

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Price per night from

$272

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

6 bedrooms
5 bathrooms

sleeps 14

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Price per night from

$1,001

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$402

Manasota Beach Vacation Rental

Englewood house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$270

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$161

Luxury Sarasota Golf Home

Sarasota house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$369

Enjoy our pool and prime location for beach, downtown and bike trail.

Venice house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$150

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$259

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

$273

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

3 bedrooms
2 bathrooms

sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

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Price per night from

$501

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

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Price per night from

$272

Luxury All Inclusive Fully Furnished House on the Gulf Coast in Venice Florida

Venice house

3 bedrooms
2 bathrooms

sleeps 2

Responds fast! avg. 54 minutes

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Price per night from

$268

Luxury accommodation in Venetia, 3 months stay

Venice house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$192

Casa Calm: King Room, Yoga, Spa

Sarasota private room

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$183

Heritage Oaks

Heritage Oaks Golf and Country Club condo

2 bedrooms
2 bathrooms

sleeps 5

Responds fast! avg. 3 hours 56 minutes

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Price per night from

$98

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$436

North Port Country Home - Close to Mineral Springs

North Port house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$259

Arnold Palmer Design 36 Holes - Lakewood National Resort

Lakewood Ranch villa

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$241

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$114

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

3 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$904

Florida Paradise Near Img Academy and Beach

Oneco house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$408

Golf Haven

Lakewood Ranch apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 36 minutes

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Price per night from

$253

Skyline Resort

Lakewood Ranch apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 36 minutes

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Price per night from

$253

Eagles Nest

Lakewood Ranch apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 36 minutes

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Price per night from

$253

Serenity Shore

Lakewood Ranch apartment

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 36 minutes

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Price per night from

$299

Dream Weavers

Lakewood Ranch apartment

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 36 minutes

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Price per night from

$287

Endless Summer

Lakewood Ranch apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 36 minutes

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Price per night from

$253

Lakeview Oasis

Lakewood Ranch condo

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 36 minutes

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All filters match

Price per night from

$253

Paradise Palms Resort at Lakewood National

Lakewood Ranch apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 36 minutes

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Price per night from

$253

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$1,032

Quiet Venice Pool Oasis (2/2)

South Venice house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$201

Sunshine Retreat- brand new 1st Floor 2/bed, 2/bath with golf & lake view

Lakewood Ranch apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 36 minutes

Match: Jacuzzi or hot tub

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Price per night from

$253

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$178

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

Match: Jacuzzi or hot tub

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Price per night from

$117

Beachplace Building 3 unit 302

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 4

Match: Jacuzzi or hot tub

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Price per night from

$187

Dream beach, pool/spa retreat!

Siesta Key house

4 bedrooms
3 bathrooms

sleeps 9

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Price per night from

$345

Bromeliad at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

Match: Jacuzzi or hot tub

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Price per night from

$490

Viewing 38 of 107
rentals in Osprey

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Osprey Rentals with Hot Tubs

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107 Houses in Osprey with hot tubs

Viewing 38 of 107rentals in Osprey

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Viewing 38 of 107
rentals in Osprey