CASA DE ROSALIE: This classic Conch home is located across from Bayview Park, with tennis courts, playground, basketball court and venue for many community activities. Built in 1889, this home has many of the original features including Dade County Pine walls in the bedrooms and a gracious banister for the stairs to the second floor.
The living room has a large flat screen TV and comfortable seating for everyone, including a queen sleeper sofa for extra guests. The layout of "Casa de Rosalie
Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool. Ecco Domani means "Here Tomorrow" which is where you'll want to be when you see what you're missing. A beautiful 3 story home with private pool, off street parking and attractive appointments -- a wonderful Key West escape that you will want to come home to year after year.
Centrally located just off Simonton Street, you are 1 block to Duval Street, wal
FLAGLER STATION (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $3,200 - $7,500 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees)
Flagler Station has been recently remodeled, refurbished and re-furnished. High speed WIFI and state-of-the-art electronics, top-of the-line gourmet kitchen and luxury linens make this home the one you'll return to year after year.
Three bright and airy bedrooms and two baths. Master king-bedded bedroo
Small quiet compound with a pool an off street parking, walking distance to great restaurants, shopping and entertainment. Relax on your balcony overlooking the saltwater pool with palm trees swaying in the breeze, a perfect picture? This lovely 2 bedroom 2 bath upstairs condo is just that. There are only 3 other condos in this secure compound that share the pool and the private outside area for lounging and grilling. Updated kitchen with granite counter tops and stainless steel appliances make
Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space. A quintessential cigar makers shotgun style house built circa in 1890s. Located in one of the most desirable historic neighborhoods of Key West – The Meadows with tree-lined streets, a tranquil atmosphere, and yet still have easy access to the endless vacation activities available in the Southernmost City. Beaches, restaurants, tennis courts, marina, night life, everything
PERFECT PINEAPPLE - (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,975 - $6,055 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees)
Long considered a sign of hospitality, the pineapple is now widely recognized as sign of Welcome and Friendship.....and so we welcome you to the Perfect Pineapple.
On the corner of Southard and Margaret streets in the historic district, this darling Key West monthly vacation rental with two bedroom
Beautifully recently remodeled 2 bed/1.5 bath condo located just 4 blocks to Duval Street and the Historic Seaport. This 2-bedroom downstairs condo offers the best of all worlds. Enter from a quiet lane into the newly painted and furnished living/dining/kitchen space. Lots of windows and french doors to let in the sunshine. Master queen bedroom is situated behind french doors with a unique bathroom ensuite. Hall bathroom has access to the tub/shower through its own private door. All stainless ki
Amazingly Perfect!!! That is how one of our guests reviewed Southard Getaway! This amazingly perfect rental can be yours as well!
Imagine it. Arrive in Key West to a beach-like home in walking distance to all that Key West has to offer. Yes, that's Southard Getaway. Two queen bedrooms upstairs with full bath, open living space downstairs with quiet, shaded deck. Decorated in hues of blue and green that remind you of the ocean a few steps away. Located in the exclusive Truman Annex gated commun
KEY LIME PIE: (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,600 - $5,775 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees)
One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town.
Refurbished with updated kitchen cabinets, countertops, and appliances. On the first floor you will find the living room, kitchen, master bedroom and bathroom. On the second floor is the guest bedr
This unique 1 bedroom, 2 bath cottage is about to become your home away from home!
Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE!
This spacious cottage with a large private covered deck, just perfect for enjoying an afternoon cocktail or a good book, overlooking shared pool almost sounds like a dream.
The home features large wheelchair accessible bathroom with a separate tub and shower, therapeutic king size bed, large flat screen TV and 1
It is all about outdoor living at this beautiful private home with large covered living space overlooking your private pool. Poolside Paradise was built with entertaining in mind. Privacy fence surrounds the intimate front yard perfect for gathering, wet bar is welcome addition in the kitchen, and wait until you see the backyard! The covered outdoor living room is larger than the one indoors, just steps from the heated 18'x24' pool. Off-street parking, BBQ grill and high-tech entertainment syste
COCONUT COTTAGE: (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,200 - $5,590 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees)
The perfect escape if you’re looking to get away from it all. Located in a quiet neighborhood of Old Town Key West, this 1 bedroom 2 bath cottage is a gorgeous spot to rest your head in our island city.
Enter the property in a cozy sitting room. The living room and kitchen are located at the back of
EMMA'S SECRET --- (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,400 - $4,525 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees)
Luxurious 2 bedroom 1 bath Key West condo, located in a historic neighborhood of Old Town with a total of 4 condos in the building. Walking distance to Duval Street, the heart of Key West with all the restaurants, specialty shops, galleries and nightlife. Hemingway's House, Truman's Little White House
EMMA'S ESCAPE -- (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,400 - $4,525 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees)
Beautiful and spacious Key West condo: two bedroom one bath located in historic Old Town's Bahama Village neighborhood.
Emma’s Escape is one of four condos within a restored historic home. The kitchen is well appointed with upgraded appliances, granite counters, and beautiful wood cabinets. The overa
HIDDEN TREASURE (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,350 - $4,625 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees)
You could easily pass by this jewel of a home without ever knowing what a fabulous rental is hidden inside. Located down Wong Song Alley behind a private fence, just a few steps from the pool and you've reached your sanctuary.
Comfortable open floor space includes living, dining and kitchen. Master bed
BOGEY'S RETREAT: (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,100 - $4,400 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees)
Located in the exclusive Golf Course community, allowing you to enjoy all that Key West has to offer while staying in a relaxing environment.
Located in the middle of the Key West Golf Course (the only course within 50 miles). Only steps away from your choice of two spa-themed private pools, and a $50
KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo.
It's not Bermuda or the Bahamas but better, a delightful 2 bedroom, 2.5 bathroom townhome in Key West, FL. Bright and sunny Kokomo offers plenty of space for monthly renters who want to settle in and live like a native. The main level of the home off
Townhouse located just steps from the Key West Golf Course Club House and after a round of golf head over to either of the two pools to cool off. Imagine yourself in a secluded, gated community steps from the golf course, minutes from the beach, airport and some of the local's favorite restaurants. Spend a month (or two) in A Slice of Paradise and you may never return home from this Key West monthly vacation home rental.
Two bedrooms, 1 full bath upstairs; open floor plan downstairs with sleepe
NEWTON'S NEST (Monthly Rental)
Newtons Nest (Monthly Rental) A quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence. A 1 bedroom condo that has been lovingly restored to showcase beautiful Dade County Pine walls, eclectic Key West furnishings and details along with premium bedding.
Entering into the Newtons Nest you are greeted by a sunny porch with seating, the perfect spot to relax with your favorite book or lounge
Ibis ( (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,250 - $4,225 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees)
Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.
Just a couple of blocks to Duval Street, walking distance to restaurants, shopping and attractions of Old Town Key West. What a great location; park your car and jump on your bike for a relaxing visit in our island ci
4 bedroom 3 bath House - 4 bedroom 3 bathroom with 2 kitchen house located on Flagler Ave about 1/2 mile from Smathers Beach. Conveniently located in center of Key West. Nice from covered porch. Walk into living room. located to left of living room is 2 bedrooms and 1 bathroom. Walk through living room on right into dining room kitchen area. off the kitchen to the right is another bedroom with a bathroom. Central AC. Great for a family or roommates. 4 bedrooms are scare these days call for a sh
Furnished 2 bed/2 bath Home with Pool and on Canal - This beautiful single family home has it all. Move right into this fully furnished home, located in New Town on a Canal, bring your kayaks and launch from your back door. This 2 bedrooms 2 bath home provides 1,258 sq ft of living space. This home features a wonderful private pool, updated kitchen, Central AC, a washer/dryer, and two off street parking spaces. Available mid-October. $4,025/mo plus utilities + $150/mo for pool maintenance for a
319 Duval Street 2/2 in Historic Women's Club Building - Available NOW - Located above the historic Woman’s Club on Duval, this meticulously renovated and well-appointed two-bedroom, 2-bath apartment combines historic character with the best of modern living. A wonderful floor plan with high ceilings and an abundance of windows fills this home with natural light. The fabulous new kitchen has stainless appliances and granite counters. Relax on the charming treetop balcony overlooking the front
Golf Course 2 Bedroom 2 1/2 Furnished House - Located at the Key West Golf Course in the sanctuary is this 2 bedroom, 2 1/2 bathroom multilevel spa home. The outside private patio features a secluded jacuzzi spa. The home is beautifully decorated with an open floor plan for the living, dining room, and kitchen area. Upstairs are 2 bedrooms each with their own bathroom. The master has access to it's own balcony. The home comes with one covered parking space. The Key West Golf Course complex has a