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Holiday Rentals near Key West Intl Airport

3491 S Roosevelt Blvd, Key West, Florida 33040
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 115 Rentals in Key West
    Sunrise Suite Key West 2 Bed Rooms 2 Full Baths1 / 36
    (93)Excellent
    0.5 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage1 / 38
    (44)Excellent
    1.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Top floor, two bedroom,two bath condo with private balcony,close to the Ocean1 / 47
    (4)Excellent
    0.5 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Ocean Vista1 / 13
    (2)Excellent
    1.0 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Ocean Views
    • Sauna
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2021
    We had an excellent time here! Not only was checking in easy, but the place was equipped with hand sanitizer on the wall and in the guest binder was a note from the cleaners...
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    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.0 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Sauna
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    Pet friendly
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.8 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Private Outdoor Pool (Heated)
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    • DVD Player
    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. Use of bicycles and four passenger electric car provide flexible transportation all over the island. The home features a modern kitchen with all appliances...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Henry's Piece Of Paradise On The Ocean In Key West1 / 20
    (37)Excellent
    1.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
    • Sauna
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2022
    Great location, especially for a family of four. We had a great time. The pool and hot tub was wonderful. Definitely need a car to get to the activities, but so nice.
    Reviewed 5 May 2018
    We stayed 5 nights. It was even better than I anticipated. The condo was secure with private parking. The kitchen had everything we needed. Loved the Key West color scheme in...
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    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condo On The Ocean with partial ocean views - rent weekly or nightly. Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean views from a 38-foot private balcony accessible from the living and...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Seaside Condo 2 pools. sunny, quiet, near Old Town1 / 17
    (2)Excellent
    0.9 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2016
    This apartment was the perfect place to experience Key West, it was sunny and quiet, right across the street from the beach and just minutes away to Old Town with it's great...
    Reviewed 11 March 2016
    This Key West getaway condo is a wonderful escape from the freezing temperatures of the northeast. I was here other years and noticed this time that there is a beautiful new...
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    About this property
    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two Olympic size swimming tools, tennis court, shuffle board court and outdoor lounging and dining areas, It is...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    'TORTOISE SHELL II' ~ Comfortable, Modern Condo Two Blocks from Duval!1 / 15
    (7)Excellent
    2.6 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    Pet friendly
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    Smoking allowed
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Truman Annex, two blocks from Duval1 / 35
    (71)Very good
    2.9 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool1 / 14
    (120)Excellent
    2.5 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Craig & Cindy Key West Truman Annex 212 Fleming House1 / 48
    (20)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    “STONE'S THROW” ~ 2 Bedroom Cottage with Shared Pool, its a PERFECT LOCATION!1 / 17
    (11)Excellent
    2.6 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Majestic Escape near Duval!  Pool, wifi, renovated 2/2 1/2, private courtyard.1 / 50
    (76)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Tom's Chicken Coop:  Nice Ocean View, Pool, Renovated, Close to Beach1 / 39
    (97)Excellent
    1.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!1 / 19
    (85)Excellent
    1.8 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Tropical Key West Get Away1 / 32
    (103)Very good
    1.7 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Secret Villa I * Old Town with Private Pool, close to Duval!1 / 24
    (80)Excellent
    2.5 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    BEST DEAL IN THE KEYS!1 / 25
    (120)Very good
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval1 / 24
    (137)Excellent
    2.3 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    TRUMAN ANNEX - FOUNDRY 71 / 20
    (32)Excellent
    2.9 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Apple of Your Eye in Paradise (Truman Annex)!1 / 24
    (59)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Attitude Key West (2 Bikes and Wireless Internet)1 / 50
    (137)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Completely renovated in 2016! Galleon Resort Efficiency Historic District1 / 33
    (43)Very good
    2.8 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!1 / 34
    (10)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 26 April 2021
    We stayed at Shipyard 206-7 by Cindy & Craig in October 2020 for 7 nights. The location is prime; not too far from Duval and all the fun activities, but def far enough away...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    A Castle on An Island  Your Santuary Retreat   Key West   Sleeps up to 201 / 30
    (2)Terrible
    0.8 miles from Key West Intl Airport
    8 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
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    About this property
    In 1926, one of the richest men in South Florida, his family owned 45 percent of the land in Key West and most all of the shrimp and fishing boats in the Keys, married a beautiful young New York socialite and wanted her to move to Key West to live with him. 'Honey', I will only move to Key West if...
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    Key West, Florida Keys
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
    Key West Golf Club - Completely Renovated - Tree House Too.1 / 18
    (11)Excellent
    1.9 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    'TIDES ON SIMONTON' ~ Perfectly located just off Duval and all the fun!1 / 18
    (110)Very good
    2.4 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!1 / 24
    (59)Excellent
    1.8 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Great location! Everything one would need. 3 month minimum1 / 13
    (6)Excellent
    2.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West1 / 37
    (62)Excellent
    2.7 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin1 / 49
    (28)Excellent
    2.6 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    'OFF CALL' ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!1 / 21
    (62)Very good
    1.7 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Harbour Place 115 in Truman Annex Key West1 / 45
    (66)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Tom's Chicken Coop:  Nice Ocean View, Pool, Renovated, Close to Beach1 / 39
    (30)Excellent
    1.2 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval1 / 27
    (130)Very good
    2.4 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Patio
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.5 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to SALT PONDS SANCTUARY! This beautifully adorned condo on the third floor of the Salt Ponds Condominium Complex in Key West boasts a private balcony to view the sunset while sipping your favorite cocktail. You are minutes from Duval Street where you can sample the many restaurants and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Downtown Location in Historic District-No Contact Check-In1 / 37
    (41)Very good
    2.1 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi1 / 24
    (88)Excellent
    2.0 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    'Oceanside Oasis' * Kings Pointe: Direct Ocean Views & 3 BR'S1 / 32
    (86)Excellent
    2.0 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Penthouse Level Ocean Views-  CHECK FOR LAST MINUTE SPECIALS1 / 40
    (138)Very good
    1.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Cable/satellite TV
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    Pet friendly
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Key West Home/Pool on the Water1 / 34
    (12)Excellent
    0.5 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Boli Townhouse - Luxury Rental in gated Truman Annex1 / 50
    (125)Excellent
    2.9 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Poppy Cottage: Historic Old Town - Beautiful Renovated Cottage for Two1 / 20
    (8)Excellent
    2.1 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 81 / 49
    (11794)Excellent
    1.7 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Poolside Breeze Retreat A103: 2  BR, 2  BA Condominium in Key West, Sleeps 61 / 49
    (86)Very good
    1.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
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    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Smuggler's Den: 3 Blocks to Downtown, Walk to Restaurants & Galleries Hot Tub1 / 29
    (4)Excellent
    2.4 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Catherine House: A charming Old Town Key West cottage1 / 29
    (153)Excellent
    2.3 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.1 / 44
    (124)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Internet Access
    • Cable/satellite TV
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    • Housekeeping Included
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 November 2021
    I have booked STARFISH in the past and have booked it again, and will not hesitate to book this property whenever my future travels include Key West, Florida. The interior of...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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