Key West Vacation Rentals

Gated Community ~ Key West Vacation Condo Rentals in Florida

Most condo rentals in Key West, FL are located in a premier gated community. The assurance of such privacy is a comfort for all travelers whether you're with a group of friends or traveling with young ones. Our gated community vacation rentals are very popular among guests for their exclusive access to amenities like community pools, hot tub and children's park and yet close to most if not all Key West activities. These extras can go a long way in keeping everyone entertained during any down time you may have during your Key West getaway.
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2 Bedrooms
1½ Baths
Sleeps 5
Type of property: Townhouse
Area: Old Town

LINGER LONGER: Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome in the President's Walk of Truman Annex, a gated community located within Old Town Key West. This property is conveniently situated poolside and just a short walk to the many restaurants, attractions and shopping that make Key West so special.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL SEA TURTLE: This 2 bedroom 2.5 bath townhome with sleeper sofa offers comfort and space for a family of six. Conveniently located in the rooftop townhome community of Duval Square, you are close enough to the eclectic activity of Duval Street, and far enough to enjoy peace and quiet in the privacy of your own home.


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Studio
1 Bath
Sleeps 2
Type of property: Cottage
Area: Old Town

OSPREY: This quaint cottage is located in The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West, just 2 blocks from Duval Street. Compact and well-appointed, it is perfect for two people who want to relax, swim and walk around Duval Street, day after day.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

CROWNER'S JEWEL: Experience the finest in Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome. Located in Truman Annex, a secluded gated community within Old Town Key West, everything you want to do is within easy walking distance -- tourist attractions, beach, bars, restaurants.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: Cottage
Area: Old Town

NAUTICAL DREAMS (monthly rental): Here's the perfect spot for whatever you desire, parties or peace & quiet. This 2 bedroom 2 bath home, in a small compound of 8 cottages, opens from each bedroom and the living room onto a grand private deck with ample space for entertaining or relaxing with a book. Walking through this well-established local neighborhood is an added bonus.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Cottage
Area: Old Town

SUNNY DAYS - Monthly rental Key West, beautifully maintained while retaining its original style and structure. Dade County pine is throughout the property, lots of French doors and windows to bring in the sunshine, and lots of privacy within the cottage grounds and within the compound community. 


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

Shrimp Party (MONTHLY RENTAL) Key West Pinks, Parties and Drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway pack your gear and settle in for a month or longer.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

LAVENDER JUNGLE: Beautiful 2 bedroom 1 bath downstairs Shipyard condo in Truman Annex with back deck that opens to the entrance of Fort Zachary Taylor State Park, one of the nicest beaches on the island. Truman Annex, a secure gated community within Old Town Key West, is within walking distance of all the favorite hotspots on the island.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: Condo
Area: Ocean Side

KEY WEST CROWN JEWEL: We know that you will enjoy staying in our little bit of Paradise. This is a 2 bedroom, 2 bath Penthouse condominium with 1350 square feet of living space. Located on the Atlantic Ocean with magnificent views from every room. A short bike ride downtown and you are in the midst of what has made Duval Street infamous: bars, restaurants, and galleries galore.


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2 Bedrooms
2 Baths
Sleeps 5
Type of property: Condo
Area: Old Town

PARROT PERCH: Located in the gated community known as Truman Annex, you are in walking distance of all the activities to experience while visiting our island paradise. This 2nd floor condo with 2 bedrooms 2 baths and sleeper sofa offers a welcome respite in a great location and a great value for a great vacation.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

CONCH WIND:   Conch Wind is the property you have been hunting for! This Conch-style townhome located in Old Town Key West is nestled in a quiet, secured compound, featuring 1 bedroom with bath ensuite on the first floor and the Master bedroom with bath ensuite upstairs. A porch and second floor balcony overlook the 50 foot pool, offering lots of room for rest and relaxation.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Stock Island

CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Open and airy, with private balconies, a grand 52" flat screen TV in the living room and well-equipped kitchen. A short walk to the community pool and a short drive to favorite local watering holes.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Private Home
Area: Old Town

ARTIST GARDEN:  A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of Truman Annex, a gated community within Old Town Key West. This property is in the ideal location, in walking distance to all Old Town has to offer, including the beautiful beach at Fort Zachary Taylor State Park.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

A BAREFOOT RETREAT: Step into this fantastic condo and the first thing you'll want to do is take off your shoes; feels just like home. Located on the main entry


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

SIESTA BAY: Beautiful 2 bedroom 1 bath 2nd floor condo in Truman Annex, just steps away from the shared pool and a short walk to Fort Zachary Taylor State Park. Anything you want to do on our island paradise is within a few blocks. Enjoy quiet solitude in this home in between visits to chaotic Duval Street, then do it again and again.


 

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