Sunset Views at the Galleon
Key West Condo
- 
4.7 Star Review
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sofa. Jacuzzi Tub in Master. Property features Pool, Sauna, Private Beach, Tiki Bar, Rooftop viewing deck, Grills and daily activities. Premium location for easy walks to Duval Street, Mallory Square, Key West Aquarium, Shipwreckers.......read more
2 Bedroom(s)
Sleeps 6
Condo
The Palm Villa, Island Oasis blocks from Duval
Key West Private vacation home
- 4.9 Star Review
BEWARE! I have been told that someone is scamming individuals by posing as me. Communicate ONLY through VRBO and make payments ONLY through VRBO. Thank you.
Come stay at The Palm Villa and experience unparalleled luxury and comfort in Key West’s historic Old Town. For 10 years we have been in the business and we are a member of The Bette.......read more
2 Bedroom(s)
Sleeps 4
Private vacation home
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
Key West Private vacation home
- 5.0 Star Review
The moment you walk thru the door you are greeted by soothing tropical colors and high vaulted ceilings.
The large master en suite is located on the first floor. It has a large closet and bathroom. The bathroom has a clawed tub and stand up shower with access to an outdoor shower if wishing to live like a local.
The Living Room is most invit.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Key West Private vacation home
****This property requires a minimum stay of 28 nights in the same calendar month****
***Brand New Pool with waterfall, saltwater, heater, and a chiller to maximize comfort!
Tropical Properties Vacation Rentals invites you to our beautiful historic home located in Historic Old Town Key West. This home is located just two blocks f.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Craig & Cindy Truman Annex Foundry Townhouses (2 bedrooms 2 1/2 baths)
Key West Private vacation home
- 5.0 Star Review
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West....Truman Annex. We offer 2 Foundry Townhouses practically adjacent to each other. Truman Annex is a six block gated community right at the entrance to Ft. Zachary Beach, 2 blocks from Duval Street, and right next to the nightl.......read more
2 Bedroom(s)
Sleeps 6
Private vacation home
ADMIRAL'S PARADISE Gorgeous Townhome in Truman Annex
Key West Private vacation home
- 4.7 Star Review
Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ceilings both on the first and second levels with hardwood floors and crown molding. Enjoy the theater style kitchen with new quartz counter tops and stainless-steel appliances with a gas cook top. The large living and dining are.......read more
2 Bedroom(s)
Sleeps 4
Private vacation home
The Cordelia, a Key West Monthly Rental
Key West Private vacation home
The Cordelia is located in a Historic Conch house from the early 1900’s updated and decorated by its owner. Features original hardwood floors, new bathroom and chic decor items. The galley-style kitchen is equipped with white quartz countertops, a black retro tile backsplash, and stainless-steel appliances; fully stocked with all the necessary ess.......read more
Studio
Sleeps 2
Private vacation home
~ VILLA AZUL ~ Luxurious "Old Town" Home w/ Private Pool & Parking!
Key West Private vacation home
- 5.0 Star Review
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!
THE PROPERTY: Villa Azul consists of two separate buildings - a main house and a separate pool house! The main house is a two-story historic cottage with Brazilian cherry hardwood floors. The spacious living room is finel.......read more
3 Bedroom(s)
Private vacation home
Key West Luxury Houseboat
Key West House boat
- 4.6 Star Review
2 BDRM 2.5 BATH. SLEEPS 6. OPEN OCEAN VIEW.
POOL, PRIVATE BEACH, RESTAURANT, BAR, GYM, TIKI, LAUNDRY ON BOARD.
15 MIN FROM DOWNTOWN.
Two queen bedrooms on first level. Open ocean view second level salon & galley, floor to ceiling windows, sliding glass doors leading to spacious fore and aft decks and spiral stairs to expansive, furnis.......read more
2 Bedroom(s)
House boat
~HORSE CONCH~ Adorable Apt in PERFECT Location w/ Breathtaking Pool!
Key West Apartment
- 4.9 Star Review
THE PROPERTY: Horse Conch is a Key West hidden gem in perhaps the best location you could imagine. The one-bedroom vacation rental is nestled in the heart of Old Town Key West (just 2 short blocks from Duval Street). You’ll love being within walking distance of everything you’ll want to experience during your tropical vacation.
Horse Conch i.......read more
Studio
Sleeps 4
Apartment
Tropical Getaway! 3 Pools, On-site Restaurant, Bike Rental, Pets Allowed!
Key West Hotel
- 4.0 Star Review
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property.
ATTENTION: The Resort Fee is not included in the daily ra.......read more
Studio
Sleeps 2
Hotel
Traveler's Palm- Fun-filled Studio w/ Pvt Deck!
Key West Apartment
- 4.8 Star Review
Summary:
Traveler\'s Palm is a second-story studio fully equipped with a private deck to relax on, cable TV and free wifi. It is located just one block away from the world famous Duval Street and is within walking distance of many Key West attractions including Fort Zachary Taylor Beach and Park, Ernest Hemingway Home and Museum, and local shops.......read more
Luxury Galleon Resort & Marina 2 Bed/2 Bath Marina View
Key West Condo
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the United States. Within walking distance to several bars and restaurants, bars, Duval Street, Mallory Square & many other historic site
About the Galleon:
Overlooking the Gulf of Mexico in historic Old Town, The Galle.......read more
2 Bedroom(s)
Sleeps 6
Condo
Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
Key West Condo
- 4.7 Star Review
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. If the dates you need are not available check my other Key West vacation rental (Henry\'.......read more
2 Bedroom(s)
Sleeps 5
Condo
Stay right on the water / Yacht Living
Key West House boat
- 4.5 Star Review
Stay on a private yacht. Located in a beautiful marina with restaurants , bars, swimming pools. The Yacht has a private stateroom and full bathroom/shower . Large aft covered deck to enjoy the amazing Key West sunrise. Sit out on the front bow to catch the sunset........read more
Studio
Sleeps 2
House boat
BOTTOMS UP BUNGALOW - 2 Bedroom / 2 Bathroom With PRIVATE POOL
Key West Private vacation home
- 5.0 Star Review
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West.
This pristine Florida Bungalow is 2 bedrooms, 2 bathroom single family home and offers all the amenities you need to make this your perfect vacation. Including off-street parking, swimming pool, quaint gazebo equipped with wet bar and custom seating. The .......read more
2 Bedroom(s)
Sleeps 6
Private vacation home
Brand New! Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
Key West Condo
- 4.8 Star Review
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale .......read more
4 Bedroom(s)
Sleeps 8
Condo
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Key West Condo
- 4.8 Star Review
Located just 2 miles from picturesque Smathers Beach, this well appointed 2 bedroom, 2 bath condo is ideally situated in Key West. Explore all Key West has to offer, located just 3 miles from vibrant Duval Street, and 4 miles from historic and majestic Mallory Square.
This two bedroom condo features a spacious king primary suite with hardwoo.......read more
2 Bedroom(s)
Sleeps 6
Condo
QUIET KEY WEST RESORT NEXT TO AIRPORT
Key West Condo
- 5.0 Star Review
Key West, FL. Available Sat. Oct.16 - Sat. 23, 2021. Located in the Southeast end of Key West at the Hyatt Windward Pointe. The unit offers a 2/2 resort-style apartment for 6 guests. Located next to the Key West Airport and a few blocks from the beaches.
Disponible del Sab. 16 al Sab. 23 de Octubre 2021. Ubicado en la parte sureste de Cayo H.......read more
2 Bedroom(s)
Sleeps
Condo
Vacation Rental in Coral Hammock
Key West Private vacation home
- 4.6 Star Review
Beautiful gated home located in Coral Hammock just minutes away from Key West. It\'s a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation.
It would work great for a family or couples or group.
On the first f.......read more
3 Bedroom(s)
Private vacation home
ANOTHER DAY IN PARADISE in the Truman Annex
Key West Condo
- 4.4 Star Review
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. This property is outfitted with washer/dryer, pots/pans, towels, linens,.......read more
2 Bedroom(s)
Sleeps 6
Condo
Waterfront 2 bedroom oasis close to Key West
Key West Private vacation home
Welcome to tranquil paradise, A stunning two bedroom two bath with water views only a 20 minute drive to Key West. Enjoy kayaking in beautiful blue clear waters surrounded by nature. The home is fully equipped perfect for long term stays.......read more
2 Bedroom(s)
Sleeps 6
Private vacation home
Studio unit at the Galleon Resort
Key West Apartment
- 5.0 Star Review
The Galleon offers studio type units that can sleep 2 to 4 people depending on the unit. All units are air-conditioned and contain a coffee maker, microwave oven, and small refrigerator. These units are a great choice for a weekend romantic getaway, or just a quick trip down the keys!
Located in the heart of Old Town Key West. This resort ov.......read more
Studio
Sleeps 2
Apartment
Beautiful & Relaxing 2 bed 2 bath condo
Key West Hotel resort
This is a large 2 bed 2 bath condo with a separate living room, kitchen, and private balcony at the Hyatt Resort. It offers a master suite & adjoining bath with a walk-in shower & a guest room with a full bath. This condo is set on the east side of the Island overlooking the Gulf of Mexico and is mere minutes away from Mallory Square for sunset wat.......read more
2 Bedroom(s)
Sleeps 6
Hotel resort
BRAND NEW HOT TUB JUNE 2022 aboard Houseboat Haven
Key West House boat
- 2.0 Star Review
Summary:
Experience Key West in a new way: aboard a luxury houseboat! The brand new hot tub aboard Houseboat Haven was replaced this June 2022!
From watching sunrise on the dock to watching sunset from the balcony, or enjoying one of the best happy hours in town, you won\'t even need to leave the Marina. Come aboard & see why life really is b.......read more
2 Bedroom(s)
Sleeps 6
House boat
Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
Key West Condo
- 4.7 Star Review
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you\'ll get without sacrificing a good night\'s sleep. The one bedroom Villa Rosa is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.
The number one reason w.......read more
Studio
Sleeps 4
Condo
SEAPORT SKYLINE at Galleon Resort near Mallory Square—Beach, King Suite
Key West Condo
OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & UNOBSTRUCTED VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO. (These views are also available from the master bedroom, living area and kitchen all day, every day)
2nd FLOOR OCEANFRONT CONDO RENTAL
Oceanfront privacy and luxury at The Galleon Resort in Old To.......read more
3 Bedroom(s)
Sleeps 6
Condo
Bonaire Suite- 1 bedroom 1.5 bath in Old Town Key West
Key West Private vacation home
- 4.7 Star Review
The Bonaire Suite is a bi-level suite decorated in a rich contemporary palm tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door.
Downstairs is a living room with sofa that converts to a queen bed and a love seat decorated with rich pa.......read more
Studio
Sleeps 6
Private vacation home
Sunset & Ocean View in Key West's Truman Annex, Bikes, Pool, Free WiFi & Parking
Key West Condo
- 5.0 Star Review
We want to let you know that your safety and comfort is our priority. Past reviews have always praised how clean our condo is and now we are stepping it up! Our professional cleaners are doing all of the right things making sure that we don\'t only look clean but that we are adhering to enhanced practices as laid out by the State and County! You wi.......read more
2 Bedroom(s)
Sleeps 4
Condo
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym
Key West Hotel
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few minutes\' walks to several local attractions. An onsite restaurant serves Latin-inspired tapas with local ingredients. The refreshing pool and pool bar are a relaxing spot to spend an afternoon in the sun. Hourly shuttle services .......read more
Studio
Sleeps 3
Hotel
Find many Hotel Options and hundreds of Beachfront Vacation Rentals in Key West.
Spend quality time with your family and friends at cheap low rates you can afford, all while near the beach, nightlife, entertainment and a wide variety of beach activities. We have historic Key West Vacation Rentals, you may even find a Vacation Rental with Boat Dock or Boat Slip. Hundreds of properties to choose from, search for availability, photos, descriptions and best price. If you visit Key West in October, make sure to book your Vacation Rental here for Fantasy Fest.