At this gorgeous Sugarloaf Key vacation home, you'll have five spacious bedrooms (including two master suites)! Enjoy beautiful Gulf views set over three acres, offering privacy for a memorable Florida escape. It's even dog-friendly! Just 18 miles from Key West, this location offers easy access to...

Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, private pool, furnished patio, and off-street parking for two...

Escape to Key West's beaches during a stay at Atlantic Ocean View, where you'll enjoy prime island location and access to a shared pool. This condo accommodates up to six, so it's a great choice for the whole family! The condo backs up to a stretch of Higgs Beach, so you're never far from the...

Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views, and more await you. Nestled on the northern side of Key West, you have easy access to the shops and restaurants of Old Town, as well as a dock and the fresh ocean air of...

Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of luxury and total relaxation. This...

Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is sure to become your new favorite...

Treat your group to a tropical getaway at this dog-friendly Key West retreat. Featuring room for up to six guests and a cute canine companion (for a small nightly fee), street parking, a private hot tub, and a shared pool, your vacation promises to be one to remember. This home is nestled in a...

Come to Key West and unwind with this comfortable and inviting two-bedroom condo! A shared pool and a private balcony with scenic views of the marsh add to the feeling of relaxation. The family dog is also welcome to join you for an additional nightly fee. This colorful rental is part of the...

Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone who plans to explore the island by...

A large group getaway to Key West starts with this pair of charming cottages, which feature a total five bedrooms, three-and-a-half bathrooms, and a max occupancy of 16. The property also includes a private heated swimming pool, a private hot tub, and dog-friendly accommodations. The cottages sit...

If you're looking for the ideal spot for your next large group getaway, then look no further than this grouping of three separate Key West condos. Boasting a shared heated pool and hot tub, and space for up to 12 guests, this home makes it easy for everyone to enjoy all of the local attractions....

Find the best of Key West at your doorstep with this beautiful two-bedroom condo, a lovely South Florida escape with a private deck and patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more! Perfectly located between Truman Annex and Bahama Village, this...

Give your family and friends the trip to the Florida Keys they deserve thanks to this condo in Key West! A great location, along with amenities like a shared pool and private parking, ensure everyone can enjoy themselves. A dog is even welcome for a small nightly fee. Courtesy Shuttle available to...

Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of four condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could hope for on a tropical...

Situated on the second floor of a historic home, this spacious dog-friendly condo welcomes guests with great amenities and a private hot tub! Soak after a long day in the sunshine, and fire up the gas grill to make full use of the back patio space. You're right around the corner from Duval...

Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Please inquire for options. Step out to your back yard for a dip in the private pool, set amid lush...

Searching for an affordable long-term vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Tune into the Windchime! This lovely studio for two comes with all the comforts you need for an extended stay away from home, along with a...

Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large historic house on Key West. Featuring a private heated pool, four private parking spaces, and a communal area with plenty of room for everyone, this seven-bedroom, eight-and-a-half bathroom house...

Surround yourself with peace, tranquility, and seaside fun when you book your trip to this Key West cottage. Enjoy the bubbling hot tub, shared pool, and easy beach access. Nestled in the Palm Gardens condo community in Old Town Key West, this tropical home embraces you with island vibes and a...

Start planning your Key West vacation when you book this three-bedroom, two-bathroom home. Up to eight guests will spend their vacation days lounging by the private pool, strolling the streets of downtown, and soaking up the Florida sun on soft sand beaches. The family dog is also welcome to join...

Treat the whole family to a seaside adventure when you book your getaway to this dog-friendly Key West cottage. Boasting a prime location close to beach activities and attractions, as well as a shared pool, this home welcomes up to six guests and a canine companion (for a small nightly fee). This...

Take your romantic getaway at this bright studio condo in the heart of Key West's historic Old Town! Free WiFi, a deck, and a kitchenette will have you feeling right at home less than a mile from the beach. Visit Fort Zachary Taylor State Park & Beach, about a mile away, where you'll find white...

Spend your Key West vacation in style here at this high-end house with a private hot tub! There's plenty of room for everybody in this house's eight bedrooms, and you're steps away from the ocean. Key West's most popular attractions surround this home - walk down to Mallory Square a few blocks...

Immerse yourself in the laid-back ambience of the Florida Keys with a stay at this colorful Key West condo! Complete with a shared pool and hot tub, tennis courts, dog-friendly policies, and a reserved parking spot, this comfortable vacation rental will have you relaxed in no time. This...

Escape to the land of sea and sun for your next vacation with this fresh condo in Key West. Featuring one bedroom and one bathroom, entertainment, and an awesome location close to all the action on the waterfront, up to four guests will love it here! The family dog is also welcome to join you for...

Come to Key West and stay in this dog-friendly accommodation with two separate living quarters, a private pool, walking distance to the beach, and close proximity to all the major attractions. This home is within walking distance to famous Duval Street and its shops, restaurants, and bars. Higgs...

Experience a piece of Key West's past when you book a stay at this charming ground-floor suite in the historic Curry House Bed & Breakfast! Up to two guests will enjoy a shared on-site pool, home comforts, and a convenient location in the heart of the city. Curry House sits three blocks off of...

Looking for the perfect Key West vacation rental to host your family reunion or corporate retreat? Your search stops with Curry House Bed & Breakfast, a nine-bedroom, nine-bathroom getaway with historic charm, modern comforts, a private swimming pool, and room for up to 18 guests. Curry House is...

Small families and close groups of friends will love this dog-friendly home for four in Key West! A shared swimming pool and nearby beach access provide everything you need for a great vacation. Your new home away from home rests comfortably by the city's Old Town, where lots of shops and...

Immerse yourself in the island lifestyle when you book this Key West accommodation, comprised of a two-bedroom house and a separate one-bedroom pool house. Featuring a private heated pool, a private parking spot, and an outdoor shower, this home gives you the chance to unwind. Four dogs are...

Take a break from the ordinary with a visit to this tropical hideaway in the heart of Key West's historic district! Ideal for a romantic getaway, this suite promises comfort, space to relax, and a prime location in Old Town. The family dog is also welcome to join you for an additional nightly fee....

If Key West is on your travel itinerary, make this lovely rental for six your home away from home and spend your time lounging by your private pool and spa. Located in Historic Bahama Village, this home is one block away from the world-famous Duval Street, where you can enjoy galleries, shops,...

Let time wash over you in gentle waves while you relax in the sunny paradise of Key West at this cozy studio condo, offering access to a shared pool, courtyard, and an easy walk to the soft sandy beach. Located in the heart of downtown Key West as part of the larger Banana Foster's Guest House,...

Escape to Key West for a romantic getaway for two and walk to the beach, dining, and other attractions when you make this cozy, efficiency studio yours. You'll be located in a quiet neighborhood and surrounded by tropical vegetation and decking for great views. You'll be within walking distance to...

Leave your worries behind with a relaxing trip to the Florida Keys courtesy of this lovely vacation home! This traditional home in Key West features modern amenities and a location perfect for sightseeing. Nestled in Key West's old town, this home for four puts you only a few blocks from both...

This colorful dog-friendly Florida home has everything you need for an unforgettable vacation, with a private swimming pool and hot tub and walking distance from the beach. Your home sits only a few blocks away from the soft sands and warm waters of Higgs Beach. If you'd prefer some shopping and...

Get away from it all and head to Key West for a sun-filled vacation with this two-bedroom, two-bath condo for six and enjoy easy access to restaurants, attractions, and the beach. You can also bring your beloved dog along for a small nightly fee! You'll be located on the northeast corner of Key...

Stay cool on your next trip to Key West with a stay at this delightful condo with a private balcony, a shared pool, and a complimentary shuttle between the rental and many of Key West's popular attractions. Located just minutes away from beaches, marinas, scuba shops, and the Key West...

Book a stay at this lovely condo for a relaxing tropical getaway in the heart of the Florida Keys! With incredible amenities like a shared pool and hot tub, lush landscaping, a private parking space, and beautiful views of the Salt Ponds Nature Preserve from your balcony this rental is truly the...

Amenities like a shared pool, dog-friendly accommodations, and a fantastic location all make this home perfect for your next trip to the Florida Keys! Your new getaway of choice is only a block away from Duval Street, right near Key West's Old Town. Shops and restaurants are easily accessible - as...

Commodore's Cove offers the best of Key West: a prime location and the amenities of home. Up to 12 can stay at this welcoming condo, so bring the whole family along! The family dog is also welcome to join you for an additional nightly fee. Stroll down to historic Duval Street a block away, where...

Escape to Key West with the family at this charming Floridian home on a quiet street with a furnished patio, private, heated swimming pool, and space for up to six guests and a dog for a small nightly fee. This home also offers off-street, private parking for one vehicle. Located alongside several...

Experience the best of Key West from the comfort of this charming studio-style cottage. A private hot tub, dog-friendly accommodations, and modern conveniences including free WiFi and a shared washer/dryer make this vacation rental perfect for everything from a laid-back retreat to an...

If you're looking for a budget-friendly home base and plan to spend most of your time enjoying the waves and exploring, this efficient studio is just the ticket. You and one other traveling companion will be in a prime location, within walking distance to the beach and Key West major attractions....

If you're looking for a convenient home base for your Key West adventure, consider this two-bedroom, one-bathroom vacation rental. Up to six guests will enjoy the convenient location, a private hot tub, a fully equipped kitchen, and more! The family dog is also welcome to join you for an additional...

Swim in the private pool, head to downtown Key West to soak up the sights, or relax in a breezy dog-friendly home - with this amazing cottage, everything is possible! Your new home away from home sits on a hill only a few blocks from the beating heart of Key West. Shopping, dining, and more can be...

This beautiful main-floor suite is the largest room in the historic Garden House Bed & Breakfast and features a semi-private porch, access to the shared pool, and a desk, making it ideal for a traveling couple or a writer's retreat. The Garden House sits just a few blocks away from both Duval...