Key West Vacation Rentals

WiFi Access | Luxury Key West Vacation Rentals

Today's vacation rentals are becoming more and more like hotels, with a variety of amenities now available in each property to help mirror a private, luxurious hotel experience. The more amenities a property has, the better the experience for the traveler.  The majority of our vacation rentals have WIFI available and is listed under Amenities.  If WIFI is an important component necessary for a successful vacation, a quick call to Reservations can ensure you have chosen a home with WIFI access.

  • Show On Map
87 Properties Returned
Page: 1 of 6  

Page Navigation

87 Properties Returned
1 of 6 Pages
Call For Availability and Pricing
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.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Private Home
Area: Old Town

AMELIA HOME:  A private Key West vacation home that is only four blocks from one of our most popular beaches on the Atlantic Ocean and one block from all the Duval Street entertainment.  This 2 bedroom 2.5 bath single family home with private pool is located in one of the most interesting neighborhoods in the historic district of Old Town Key West.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

Breezy Bungalow - Weekly Rental When a name says it all you know you know you have made the perfect choice for your Key West island escape. Bright and colorful


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

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.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Cottage
Area: Old Town

GREEN ORCHID (monthly rental): Dreaming of living like a local in Key West? Dream no more. Green Orchid offers a true Conch Cottage experience situated on a narrow lane in one of the last historic Old Town neighborhoods. Inside you'll live with all the modern conveniences and furnishings; outside you'll feel you've been transported to years gone by.


Call For Availability and Pricing
4 Bedrooms
3 Baths
Sleeps 8
Type of property: Luxury
Area: Old Town

CASA ON CASA--  So simple yet elegant, intimate yet spacious, "Casa on Casa"; offers a unique Key West experience that will linger in your memory for years to come. Located in the exclusive Casa Marina neighborhood, it is separated from the beach by a park with a fitness circuit, dog park, playground, tennis courts and pickleball courts. The historic Casa Marina hotel is at the other end of the block, and all of Old Town is a quick bike ride away.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

LEEWARD ISLE KEY WEST RETREAT: Dwell in the possibility! 2 bedrooms 2 baths in this newly renovated residence. From the moment you park in the private parking lot, you know you are someplace special. A small gated compound with only 13 homes, you will revel in the peace and quiet, while still being located right in the heart of Old Town.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

KEY WEST FOUND:   A striking 2 bedroom, 2.5 bath townhome located in the historic  Foundry building in Truman Annex. This 3-story townhome has all the comforts of home.  Conveniently located within walking distance of all the best of Key West -- tourist attractions, beach, Duval Street, Sunset celebration -- you will never want to leave.


Call For Availability and Pricing
5 Bedrooms
5½ Baths
Sleeps 12
Type of property: Private Home
Area: Old Town

CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street, you'll spend most of your time in the magnificent pool in your private backyard. Duval Street, pool and sunshine - a perfect recipe for Key West living.


Call For Availability and Pricing
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.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

THE HEMINGWAY: A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. Just steps away from the community pool and only 2 blocks from famous Duval Street and historic Old Town Key West. Relax on your back porch, take a dip in the pool, and check out the sights that you have heard so much about on our Island paradise.


Call For Availability and Pricing
3 Bedrooms
3 Baths
Sleeps 8
Type of property: Townhouse
Area: Stock Island

Coral Casita - Weekly Vacation Rental Completely Re-Designed, Re-Decorated and Ready for your island adventures! When Key West is calling your name and nothing else will do. Spacious 3-bedroom townhome in the Coral Hammock gated community with pool - designer decorated.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

EMMA'S SECRET (monthly rental):  Luxurious 2 bedroom 1 bath condominium located in the historic Bahama Village neighborhood of Old Town offers all the amenities of home.  Enjoy the tropical backyard ambience with jacuzzi, pool and tiki hut.   Located in walking distance to Duval Street, the heart of Key West with all the activities, restaurants, speciality shops and nightlife.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL ON THE SQUARE (monthly rental):  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.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

ISLAND WIND: Welcome to a tropical sun-drenched oasis in the heart of Old Town. This charming 2 bedroom 2 bath Bahamian-style townhome, with tin roof and white spindled decks reminiscent of Old Key West, is located in award-winning Windward Park, a gated and secure compound. Soothe your weary muscles in your private jacuzzi after taking in the sights all day.


 

Search Result Page Navigation: