PROPERTY OVERVIEW This 4BR/1.5BA tropical retreat is situated in a lush gated community, enveloped by Spanish lime trees, hibiscus, orchids, and a wide variety of beautiful species and exotic palms. In a prime locale, you’ll be within minutes of everything Old Town Key West has to offer. Walk...

Quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking. Here is your dream come true. Centrally located on one of Old Town's most popular streets, nestled in a tranquil corner of a sought-after gated compound with lushly landscaped walkways leading to the...

Relax Key West Style in this 3 Bedroom 3 Bath Pool Home. The spacious kitchen area flows out to the Tropical Inspired Deck via sliding doors, Foosball Table, Cushioned Seating all around and a Tiki Hut. This home is located in the heart of Old Town with a large fenced yard for outdoor living. Two...

You are so close to the large community pool that you will be able to hear the waterfall in this beautifully landscaped area. This is a very unique home where the original owner has kept this little treasure all to herself and now wants to share it with you! An accomplished artist, the home is...

South Oceanside at 1800 Atlantic is a 2 bedroom 2 bath monthly rental. The property is in an excellent location in the complex facing the tropical gardens. This Property can be your home away from home with all the modern amenities you desire. South Oceanside is tiled throughout and freshly...

Private conch home in a quiet neighborhood but still within walking distance to all of the Key West sites. Here's a little gem in a long-established local residential neighborhood just across from the Key West historic cemetery (quiet neighbors). Spacious downstairs with living/dining area that...

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...

PROPERTY OVERVIEW Situated in the exclusive gated enclave of Old Town Villas at Key West, this stunning brand-new 3BR/3.5BA townhome offers a private elevator, patio, five balconies, and community pool access. Relax in one of two living rooms with large HD TVs, or simply watch the sun set from the...

Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops. Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded compound surrounded by lush tropical foliage make...

In the heart of downtown Key West easy walking to great restaurants and shops. Living at Ground Zero was never so easy. This 2-bedroom home is steps away from the historic Mile Marker 0 that marks the beginning of federal highway U.S. 1 (which continues up the East coast 2400 miles away ending in...

Ocean views from your wrap around balcony and the Olympic sized pool await you at this beautiful home. Ocean views and tropical breezes await your arrival to this 2 bedroom 2 bathroom condominium with wrap around balconies on the 3rd floor of the condo building. Suited for 4 people with two King...

Private home that accommodates 8 guests to enjoy the large outdoor dining area while viewing your private pool in your fenced yard. This classic 3-bedroom Conch home is located across the street from Bayview Park, with tennis courts, playground, basketball court and community activities. Built in...

This beautiful studio is the perfect spot for your next Florida Keys getaway! The central A/C and ceiling fans help keep the heat at bay, while the shared pool offers another way to cool off. This studio has been designed with comfort in mind, offering large windows for natural sunlight and plenty...

Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool. Key West Pinks, parties and drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway to Key West is...

In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point. This timeless private conch home just steps away from the Hemingway House and the Key West Lighthouse a perfect location to be...

Located in one of the most sought out neighborhoods 'The Meadows' this lovely condo has everything you need to enjoy your time in Key West. Nestled in the ever popular local residential neighborhood known as The Meadows, this sweet spot is a 2-bedroom 2-bath upper level condo in a home with a...

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,...

This family-friendly Key West home features five separate villas grouped together, a shared pool, and a location that puts you close to all of the action. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Located on Center Street, this home is just a mile from the Key West...

Leave behind all of your worries and whisk your loved ones off to this two-bedroom, two-and-a-half bathroom home on Sunset Key! This private island home surrounds you with nothing but natural beauty, gorgeous beaches, and high-quality amenities. Your home is nestled on the private island of Sunset...

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...

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...

Completely remodeled, renovated and freshly painted 3 bedroom, 3 bath, 2 level Key West townhome is about to be your home away from home! Located in the private, gated community of Coral Hammock which is a short car ride away from downtown of Key West. Conveniently located just down the street...

Escape to Key West and stay in this lovely waterfront home for a luxurious getaway. Your group will enjoy a private pool, a Jacuzzi tub, and a balcony with sweeping ocean views. You'll be centrally located in the heart of Key West in the exclusive Key Cove community. Walk to grocery stores and a...

Get ready to see a whole new side of the sunshine state from the comfort of this home in Key West. You'll enjoy perks like a private pool, as well as a great location just a few blocks from the beach! Nestled on the eastern edge of Key West, this home is a short walk from the soft sands of Higgs...

Stay in style in the heart of Key West's historic downtown, where you're steps from the beach and all Duval Street has to offer! Your back patio houses a private hot tub, dog-friendly accommodations, and grill, perfect for lounging with the group after a long day of play. You're located on...

Enjoy this classic Key West cottage featuring a shared pool and a furnished patio, located within blocks of beaches, shops, restaurants, and museums! You can even bring the family dog for a small nightly fee. If you're here for the sand and sun, several local beaches are located less than a mile...

In an unbeatable location in the heart of downtown Key West, this beautiful modern condo is perfect for your Florida Keys escape. This condo features two shared heated pools surrounded by tropical gardens. The central A/C helps to keep the Florida heat at bay, while the three covered balconies are...

Book your romantic escape to this dog-friendly Key West home. With access to a shared pool and a great location on Duval Street, you'll be able to slip into vacation mode in no time. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am This home is just a block from the Ernest...

Escape to paradise at this family-friendly, three-bedroom Key West townhouse with a full, modern kitchen, furnished deck, and a shared on-site pool - all close to shops, beaches, and local attractions. This townhouse is within walking distance of many of Key West's most popular destinations,...

Soft sands, cool drinks, and breathtaking sunsets are at your fingertips at this Key West condo. You'll be moments from beaches, bars, and restaurants, with shared perks like a pool and hot tub waiting back at the building! You and your loved ones will love this home's location on Stock Island,...

Let this elegant, waterfront rental in Key West serve as home base for your next Florida vacation, and enjoy a private pool and covered deck with ocean views, among other fine amenities. The rental is located in the private community of Key Cove Landings within walking distance to the essentials...

This cozy Key West rental is ready to be your home away from home! Located on a tree-lined street in the Truman Annex community, this townhouse offers a full kitchen, patio, and a shared pool. Just a half-mile away, experience the excitement of Duval Street for shopping, dining, and entertainment....

Luxury awaits in this cozy yet spacious four-bedroom, four-bath Key West home, featuring a private pool and Jacuzzi, as well as close proximity to all the major locations. It's ideal for multiple families and large groups offering accommodations for up to 10. You'll enjoy the out-of-the-way...

Suprise your special someone with a stay at this charming and colorful Key West retreat! Set right in the heart of downtown, this home offers the perfect opportunity to enjoy a sun-kissed vacation you'll never forget. Located steps from the intersection of Truman Avenue and Whitehead Street, this...

Make your next stay in the Florida Keys one to remember with this amazing home in Key West! Three bedrooms, three bathrooms, dog-friendly accommodations, and a shared pool ensure your next trip to the tropics will be one you'll always remember. Your home is only a block away from the famous shops...

Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private pool completely surrounded by a rustling wall of palm trees, this upscale rental offers a private, tranquil getaway right in the bustling heart of Key West. This home...

Ideal for families, this dog-friendly home is perfectly placed for fun in the Florida Keys. Perks like a private pool will keep you comfy between enjoying the sand, sun, and surf of the tropics! While the immediate neighborhood is low-key, this home is still close enough to Truman Avenue to enjoy...

Enjoy the incredible location and amenities of this Key West condo. The central A/C and shared pool help keep the heat away, while the shared hot tub is a great place to spend cooler evenings. What's Nearby: This condo is tucked away from the hustle and bustle, but still within walking distance...

Enjoy the unbeatable location of this two-bedroom, dog-friendly Key West townhouse. This home features four covered balconies, including one that overlooks the community pool and central courtyard. Ceiling fans and central A/C keep the Florida heat at bay, while the private grill is great for a...

This lovely four-bedroom, four-bath home for 10 provides a prime location and excellent amenities, including a private pool, a Jacuzzi, and a covered balcony with sweeping ocean views. You'll be located on the north side of Key West in the exclusive Key Cove community. Walk to a shopping center,...

This Key West condo boasts deluxe amenities like a shared outdoor pool, a hot tub, tennis courts, and a fitness room. It has everything you need for a memorable Florida Keys getaway! What’s nearby: Located right near the water, you’ll be in a prime spot to sample all of the island's many charms....

Slip into vacation mode at this dog-friendly Key West cottage. Featuring room for up to four people, two levels, a shared pool, and easy access to all of the seaside action, this home promises to make your next vacation fun-filled and hassle-free! Notice: This is in a residential area, Quiet Hours...

This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street. Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mallory Square, you'll be able to get out and about with ease. With fresh seafood restaurants and...

Take a page out of literary history when you escape to this landmark apartment in Old Town Key West, a legendary hotel suite-turned-residence where Ernest Hemingway finished writing his iconic World War I novel, A Farewell to Arms. This century-old apartment is located in what was once the...

This stunning property overlooking the Gulf of Mexico boasts panoramic views from nearly every room and the private pool. Designed with hand scraped bamboo floors and a beautiful wraparound deck with several different seating options, this waterfront home is perfect for families or group getaways....

This four-bedroom, three-and-a-half-bath Key West home has a private heated pool, a covered lanai, and an upper deck, as well as beautiful views from every window. It's situated in the exclusive Key Cove Landings, right on the water and within walking distance to grocery shopping, restaurants, and...

Enjoy the unbeatable location of this Key West studio. A ceiling fan and window unit A/C helps keep the Florida heat at bay, while the shared courtyard and covered porches are a great place to enjoy the evenings. What's nearby: This cozy studio apartment is located in a quiet neighborhood with...