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Private pool
Wireless Internet
Air conditioning
Swimming pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
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DVD player
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Private tennis court
Cot available
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Safe
Dishwasher
Satellite TV
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Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
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Shared outdoor pool (heated)
Clothes dryer
Cribs
Ceiling Fans
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Video player
Bicycles available
Boat available
Stove
Solarium or roof terrace
TV
Central heating
Stereo system
Kettle
Toaster
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Staffed property
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Linen provided
Towels provided
Climbing frame
Swing set or jungle gym
Trampoline
Private fishing lake or river
Housekeeping Included

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Pets
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Smoking - Ask
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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
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Golf course on site or within 15 min walk
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Beach or lakeside relaxation
Golf within 30mins drive
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43 house rentals

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Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

3 bedrooms
4 bathrooms

sleeps 8

Match: Staffed property Private pool

All filters match

Price per night from

$316

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$482

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private pool, Staffed property

1 of 2 filters match

Price per night from

$976

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Private pool, Staffed property

1 of 2 filters match

Price per night from

$915

BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$382

Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$478

Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$458

Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials

Key West apartment

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$840

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private pool, Staffed property

1 of 2 filters match

Price per night from

$912

SEAPORT PANORAMA at Galleon Resort (Beach-Pool & Hot Tub-BBQ-55” TV-Jacuzzi)

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private pool, Staffed property

1 of 2 filters match

Price per night from

$912

Private, heated pool. Private yard.

Key West condo

1 bedroom
1 bathroom

sleeps 2

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$172

Key West House

Key West house

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$689

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$1,145

Tranquility by Smathers and 10 minute bike downtown Key West value savings

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$802

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Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$974

Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$1,145

Ocean View Monthly Rental at 1800 Atlantic- Open Nov, December & January

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$172

Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$478

Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District

Key West apartment

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$1,718

Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$382

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$764

Key West Affordable Ocean View Condo. Clean priced well on the Atlantic

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$745

Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$859

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$974

Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$382

Somewhere on the Beach a dream property all amenities included simply amazing

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$1,432

Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$859

Harbor Walk Hideaways

Key West b&b

4 bedrooms
3 bathrooms

sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$1,300

Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park

Key West apartment

2 bedrooms
1 bathroom

sleeps 4

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$573

Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

Key West house

1 bedroom
1 bathroom

sleeps 4

“The perfect place to stay in Key West” This property is just 1 block off Duval -- but closer to the quiet, quaint side. I was so impressed with the accomodations -- fully equipped! We could have stayed there a month! The grounds are beautiful, lush, tropical and quiet. Staff was super friendly -- it is also very private with a large locking wrought iron gate keeping the units apart from the street -- we loved everything about it! We will stay here again on our next visit for sure!~

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$796

Atlantic Paradise Found modern luxury Best pool in Key West fine finishes

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$1,374

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

5 bedrooms
6 bathrooms

sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

1 of 2 match: Staffed property, Private pool

1 of 2 filters match

Price per night from

$2,119