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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Washing machine
Garden
Internet access
DVD player
Fireplace
Private tennis court
Cot available
Sauna
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Video player
Fax machine
Pool or snooker table
Table tennis
Ceiling Fans
Games room
Clothes dryer
Boat available
Cribs
Shared outdoor pool (heated)
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Linen provided
Staffed property
Hair dryer
Telephone
Solarium or roof terrace
TV
Central heating
Stereo system
Kettle
Toaster
Iron
Stove
Private fishing lake or river
Fridge
Freezer
Microwave
Towels provided
Bicycles available
Climbing frame
Swing set or jungle gym
Trampoline
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible
Secure parking

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Mountain Views
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
Waterfront

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350 Houses

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CKBH (Casey Key Beach House)

Osprey house

3 bedrooms
3 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$652

Great rentals within 20 miles that match your search

Seasonal Rental

Venice house

2 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$292

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

3 bedrooms
2 bathrooms

sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$627

Total Retreat - Two Living Rooms, Awesome Lake View - close Beaches & Shopping

Englewood villa

4 bedrooms
3 bathrooms

sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$194

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$685

Another Day in Paradise

Siesta Key house

3 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 1 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$543

Venice Pool Home Centrally Located, Just Waiting For You

Venice house

3 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$274

Condo wOcean view on Siesta

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 1 hour 33 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$400

Paradise 3 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy

Braden River house

3 bedrooms
2 bathrooms

sleeps 10

Responds fast! avg. 9 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$371

Newly remodeled open concept 3 bed, 2 bath with heated pool and screened lanai!

Sarasota house

3 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$571

Paradise 4 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy

North Sarasota house

4 bedrooms
3 bathrooms

sleeps 10

Responds fast! avg. 9 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$429

Dream beach, pool/spa retreat!

Siesta Key house

4 bedrooms
3 bathrooms

sleeps 9

Match: Private outdoor pool (heated)

All filters match

Price per night from

$343

Southern Birdie: Large 4/3 Heated Pool Home w/ fenced in yard, close to beaches!

Oneco house

4 bedrooms
3 bathrooms

sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$314

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

2 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$223

The Hideaway: 4/2 W Heated Pool and Outdoor Spaces, 10 mins to Sarasota Beach

Gulf Gate Estates house

4 bedrooms
2 bathrooms

sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$371

Oceanfront home

Gulf Gate Estates house

3 bedrooms
2 bathrooms

sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$687

Updated Home, Saltwater Pool/Spa, BBQ, Pond Views, 6 Min Bike Ride to Siesta Key

Siesta Key house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 4 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$228

Captiva Paradise Home close to IMG Academy & Siesta Key Beach

Bradenton house

3 bedrooms
2 bathrooms

sleeps 10

Responds fast! avg. 9 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$373

NEAR IMG ACADEMY AND SIESTA KEY BEACH PARADISE

Bradenton house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 9 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$430

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

4 bedrooms
4 bathrooms

sleeps 12

Match: Private outdoor pool (heated)

All filters match

Price per night from

$717

Mid Century Home With Private Heated Pool

Tallevast house

2 bedrooms
2 bathrooms

sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$183

Stunning & Bright Sarasota Home

Sarasota house

3 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$396

Doveplum 724 at Midnight Cove Siesta Key, FL.

Sarasota townhouse

2 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$168

Chinaberry 456 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$265

Chinaberry 922 at Midnight Cove Siesta Key, FL.

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$172

Doveplum 221 at Midnight Cove Siesta Key, FL.

Sarasota house

2 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$257

Firethorn 830 at Midnight Cove Siesta Key

Sarasota house

2 bedrooms
1 bathroom

sleeps 4

Match: Private outdoor pool (heated)

All filters match

Price per night from

$143

Firethorn 322 at Midnight Cove Siesta Key, FL.

Sarasota apartment

2 bedrooms
1 bathroom

sleeps 4

Match: Private outdoor pool (heated)

All filters match

Price per night from

$250

Chinaberry 924 at Midnight Cove Siesta Key, FL.

Sarasota house

2 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$172

Firethorn 612 at Midnight Cove Siesta Key, FL.

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 4

Match: Private outdoor pool (heated)

All filters match

Price per night from

$143

Siesta key Guest House 5 star on the water Private

Siesta Key guest house

1 bedroom
1 bathroom

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$230

THE LIDO RESIDENCE

Lido Key house

4 bedrooms
3 bathrooms

sleeps 12

Match: Private outdoor pool (heated)

All filters match

Price per night from

$778

"Pelican Nest" Private Beach & Bay access & Heated Pool, BBQ, Bikes sleeps 10

Englewood villa

3 bedrooms
3 bathrooms

sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$974

Hibiscis Hideout Pool/Hot Tub Home

Pinecraft house

3 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$258

Craig House with Heated Pool

Bradenton house

3 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$206

Remodeled 4BR Pool Home / Golf View/Near Beaches

South Bradenton house

4 bedrooms
3 bathrooms

sleeps 14

Match: Private outdoor pool (heated)

All filters match

Price per night from

$516

Lovely Siesta Key house with heated pool - A block away from Siesta beach!

Siesta Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$492

Buena Vida: By Beachside Management

Siesta Key house

4 bedrooms
5 bathrooms

sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$515

Viewing 38 of 350
rentals in Osprey

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Osprey Rentals

Per night

350 Houses

Viewing 38 of 350rentals in Osprey

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Viewing 38 of 350
rentals in Osprey