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Community Pool ~ Vacation Rentals ~ Key West ~ Amenities

Rental condos in Key West offer guests exclusive access to the community pool where families and children can spend a day lounging poolside or playing water games. Heated community pools are a popular amenity and a great addition to any vacation rental in Key West when you find the beach is bustling with too many travelers or you have small children that you'd like to keep an eye on. Work on your tan while you enjoy the latest best-seller at your rental's community pool. Comfortable beach chairs and tables with umbrellas where you can enjoy a picnic are on hand to help complete your day.

Your search has found 58 homes
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Showing homes 1 - 25 of 58

TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
1 bath
$1,300 -
$2,791

SHIPYARD TREASURE: 2 bedroom 1 bath upstairs condo centrally located to all the sights and attractions of Old Town Key West including the beach at Fort Zachary Taylor State Park. Enjoy a cocktail on your balcony while watching the people stroll by and let the tropical breezes refresh your senses. ASK ABOUT OUR SPECIAL MONTHLY RATES DURING SUMMER 2012.



GOLF COURSE 2 Bed Condo - Monthly Key West, FL 2 bedrooms
1.5 baths
 

LAKEVIEW (monthly rental): Come to Key West where the sun always shines!! Stay in a beautiful 2 bedroom 1.5 bath bungalow in the gated Key West Golf Club community. Stroll the lushly landscaped grounds, relax in the pool, play a round of golf, and when you venture out, you will be close to it all - beaches, downtown and some of our favorite local restaurants.



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$345 -
$3,369

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.



GOLF COURSE 2 Bed Condo - Monthly Key West, FL 2 bedrooms
2.5 baths
 

BIRD'S NEST (monthly rental): Come to Key West, where the sun always shines! Stay in a beautiful 2 bedroom 2.5 bath townhome in the gated Key West Golf Club community. Stroll in quiet solitude through the manicured grounds, relax by the pool, play a round of golf. You're close to it all - beaches, downtown, the airport and some of Key West locals' favorite bars/restaurants.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$2,200 -
$4,250

TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. Located in the exclusive Harbour Place complex, it has all the comforts of home and more.  Conveniently located in Truman Annex, within walking distance of all Key West activities, you'll be tempted to return again and again.



CORAL HAMMOCK 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$150 -
$1,906

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.



OLD TOWN 2 Bedroom Home Key West, FL 2 bedrooms
2 baths
$250 -
$2,755

SOUTHERN WIND: A renovated 2 bedroom 2 bath 2-story home located in the Windward Park compound in the heart of Old Town, 1 block from Duval Street and walking distance to the sights and attractions of the Historic district. This home is equipped with all the comforts of home and more. Nestled in the far corner of the compound adds privacy to this home away from home.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$1,300 -
$2,791

BEACH HOUSE CONDO:   A beautiful 2 bedroom 2 bath Shipyard condominium with private jacuzzi, located in the prestigious Truman Annex community. This gated community in Old Town Key West is ideal -- only 2 blocks from bars, restaurants and shopping on famous Duval Street and walking distance to all of the attractions you came here to see.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$1,300 -
$2,791

CONCH CONDO: This 2 bedroom 2 bath second-floor condo features a fully-equipped kitchen, home theatre in the living room, plasma TVs in both bedrooms, soaring cathedral ceilings with ceiling fans and central air conditioning. Located in Truman Annex within walking distance of everything Key West has to offer; you have found a true Paradise.



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$300 -
$3,031

A ZEN GARDEN: The perfect 2 bedroom, 2 bath Ocean View condominium at 1800 Atlantic Condominiums for focusing on what is important in life. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated with your comfort and relaxation in mind. The BBQ, pool, Jacuzzi, tennis courts and small private beach add to your vacation pleasure.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$240 -
$2,900

ARTIST HOUSE: Located within the gated rooftop community of Duval Square, this 2 bedroom 2.5 bath with sleeper sofa and beautifully decorated, is perfectly located so that you can park your car in the private lot and walk downstairs to restaurants, specialty stores, attractions and nightlife of Old Town Key West. When you have had your fill, soak in the jacuzzi on your private deck.



OLD TOWN Key West, FL 2 bedrooms
2.5 baths
 

DUVAL ON THE SQUARE - Located at the Duval Square townhomes directly on Duval but above all the hubbub. The townhomes are built on the second and third story of the complex with community pool overlooking Duval Street. This lovely 2 bedroom 2.5 bath townhome is available for a relaxing, luxurious month in Paradise.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
1 bath
$1,100 -
$2,538

FINN KEY:   Beautiful 2 bedroom 1 bath downstairs condominium with all the modern conveniences located in Truman Annex, steps away from the community pool and walking distance to Fort Taylor State Park for beach and sunset views.   Just 2 blocks from Duval Street and the attractions of historic Old Town Key West.  Everything you're looking for within easy reach.



CORAL HAMMOCK 2 Bedroom Condo Key West, FL 2 bedrooms
3 baths
$150 -
$1,906

CORAL SUITE: If you're looking for a home away from home that will leave you with money in your pocket, Coral Suite is the place for you. This 2 bedroom 2.5 bath townhome in the gated community of Coral Hammock has all the comforts including flatscreen TVs, washer/dryer, private parking, WIFI, and convenient to some of our local favorite restaurants, beach and airport.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
1 bath
 

SUNNY DAYS (monthly rental): Beautifully maintained while retaining its original style and structure, this quaint 2 bedroom 1 bath cottage has Dade County pine throughout the property adding a feel of old Key West. The furnishings are tasteful and comfortable, the neighbors in this intimate compound are friendly and the pool and jacuzzi are inviting.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$225 -
$2,719

CARIBBEAN DUVAL:  Nestled above Duval Street in the heart of the Art district, this lovely 2 bedroom, 2.5 bath townhouse, a spacious 1,300 sq. ft. hideaway, features central A/C and an open floor plan with a half bath on the first floor and a full bath in each bedroom upstairs. Duval Square, a gated, secure rooftop community with pool is centrally located in Old Town Key West.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$240 -
$2,900

SPA ON DUVAL: A tropical 2-story, 2 bedroom 2.5bath townhome located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, specialty shops and the action of Duval Street. Catch the rays on the pool deck or soothe tired muscles in the private jacuzzi on your own deck. Spa On Duval is truly a Key West experience to enjoy.



GOLF COURSE 4 Bed Home - Monthly Key West, FL 4 bedrooms
2.5 baths
 

CASA LAGUNA (monthly rental): Spacious accommodations with 3 bedrooms 3 bathrooms plus den in a private home located at the Key West Golf Club. This home offers fantastic views to sit and relax, watch the golfers and enjoy peace and solitude. When you crave some action, the beach and some of our finest local restaurants are minutes away.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$1,500 -
$2,900

A PLACE IN PARADISE:  You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in prestigious Truman Annex. Spend your vacation in a quiet gated community surrounded by historic buildings and tropical flora that exemplifies the best of Key West. Walk two blocks to all that Duval Street has to offer.



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$225 -
$2,381

BRISA DEL MAR: This 2 bedroom, 2 bath condominium is located oceanfront in a gated community with a spectacular view of the Atlantic Ocean. Walk across the street to the beach and rent umbrellas, chairs, kayaks; enjoy a sno-cone after playing volleyball or just sit on your balcony and relax in the tropical breezes with a margarita.  Now, this is livin'...



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$220 -
$2,281

FLORIDA PALM: 2 bedroom 2 bath condominium with sleeper sofa offers your family the peace and tranquility you want while home, within minutes of the hectic lifestyle of downtown. Condo complex offer jacuzzi, pool, BBQ and tennis courts for your vacation pleasure. Located next to Smathers Beach where you can walk to promenade on the Atlantic Ocean witnessing magnificent sunrise.



TRUMAN ANNEX 2 Bedroom Condo KEY WEST, FL 2 bedrooms
2.5 baths
$1,500 -
$3,154

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.



TRUMAN ANNEX 2 Bedroom Condo KEY WEST, FL 2 bedrooms
1 bath
$1,100 -
$2,538

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.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$2,200 -
$4,250

SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in secluded Truman Annex. Lots of open spaces, perfect for entertainig or keeping it low-key and intimate. Easy walking distance to all Key West has to offer.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

CONCH ESCAPE (monthly rental): 2 bedroom 2 bath cottage in a quiet Old Town neighborhood, this property has a renovated kitchen and other recent updates making it comfortable and inviting. Enjoy a cocktail on the private deck in your own backyard, or stroll over the the pool shared by an intimate group of neighbors.



1 2 3 Next
Showing homes 1 - 25 of 58