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...

Escape to the sunshine and soft sands of the Florida Keys with this amazing dog-friendly home in Sunrise Suites Resort in Key West with a shared pool and a complimentary shuttle. With the resort's complimentary shuttle, it's easy to get to the airport and the ferry terminal. Enjoy bird watching...

Escape to the Florida Keys for a relaxing vacation in this three-bedroom, two-and-a-half bath home for eight (six comfortably) with a private pool and walking distance to the beach and Duval Street. And your favorite canine friend is also welcome for a small nightly fee. This rental is mere blocks...

Grab your sunglasses, your beach towel, and charge your camera for a visit to this Key West home, once the winter home of Pulitzer Prize-winning cartoonist Jeff MacNelly. Offering a family-friendly atmosphere and a pristine shared pool, this home gives you the chance to experience the best of...

Grab your sunglasses, bathing suit, and sunscreen and get ready to dive into the beach lifestyle when you book this Key West condo. Boasting a shared pool to stay cool, this home gives you the chance to slip into vacation mode with ease. This condo is just two blocks from Fort Zachary Taylor...

Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. With room for up to four guests to a shared pool and beach lifestyle, this home will make it easy to slip into vacation mode! Located in the Truman Annex, a quick five minute walk...

Paradise awaits when you book your next Florida vacation at this lovely two-bedroom condo on the sunny shores of Key West. With lush tropical landscaping and exclusive resort amenities like a pool, hot tub, and tennis courts, you'll never want to leave! This rental is located in the upscale resort...

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...

Tropical comfort abounds when you stay at this wonderful condo on the shores of Key West. Complete with a shared pool & hot tub, tennis courts, and a private, covered parking space, you'll have everything you need for an unforgettable Florida Keys escape. One dog is allowed for a small nightly fee....

This Key West home is waiting for you and your group of up to nine to come make yourselves at home and enjoy lazy days by your private pool. You'll be within easy reach of the beach, parks, and all the necessities. Walk to Higgs Beach and the pier, Indigenous Park, and dinner at Salute, then...

Sip a mug of coffee on the balcony as you take in views of the Florida sunrise at this superb Key West condo. Complete with luxurious amenities like a community pool and hot tub, a private parking space, and a dog-friendly policy, this wonderful vacation rental is sure to delight. The condo is...

Treat yourself to a much-needed getaway filled with stress-free days and sun-soaked afternoons when you book your escape to this Key West retreat. Offering the chance to enjoy a private hot tub, street parking, a shared pool, and easy beach access, this home will make sure your stay is one to...

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...

Find the utmost in beauty and convenience at this two-bedroom Key West home, a light-filled escape with a private patio, a heated community pool, and an ideal location close to beaches, nightlife, restaurants, and historic sites. You'll find this elegant home in the Truman Annex neighborhood of...

Escape to Florida and stay in this private dog-friendly home for six for your Key West retreat and enjoy a private pool, wraparound deck, and patio. You'll be tucked away in a quiet Key West neighborhood, surrounded by lush foliage, and you'll be within walking distance of eateries, a market, and...

Ideal for a romantic getaway to Key West, this cozy, tropical-themed studio offers a shared swimming pool, outdoor seating and dining areas, a sun deck, and convenient access to exciting destinations like Duval Street, marinas, historic landmarks, and local beaches. The Garden House offers private,...

Soak up the sun and kiss your stress away at this welcoming dog-friendly condo on Key West. The peace from the balcony will inspire your dreams for months to come! The central location makes for a convenient home base, whether your plans include a visit to the Butterfly Conservatory, The Hemingway...

Bask in the allure of old town Key West at this dog-friendly condo, where you'll have a private hot tub and deck, a community swimming pool, and enviable access to beaches, shops, and wonderful restaurants. Located mere steps from Duval Street and verdant tropical gardens, this Duval Square condo...

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...

Get the most out of your vacation days when you book this charming room at the historic Curry House Bed and Breakfast. With room for two and access to a shared pool, this vacation rental is perfect for a quick weekend getaway, a weeklong romantic retreat, and everything in between! When you stay...

See the best of Key West without breaking the bank when you book this cozy main-floor studio, which includes access to a shared heated pool and an unbeatable location in the heart of the city. Famous Duval Street - home to nightclubs, restaurants, stores, and more - is just two blocks away, as is...

Explore Key West with this conveniently located, dog-friendly condo as your home base! Duval Street's famous array of bars, shopping, and eateries is just outside your door. Explore the neighborhood's historic sights like the Ernest Hemingway House, about five blocks away. Stroll four blocks the...

Luxury and convenience combine in this recently renovated one-bedroom, one-bathroom condo in Key West. You'll love the shared pool, full kitchen, and various entertainment close to all the excitement of downtown! Sitting on the uppermost floor of a building surrounded by palm trees, you'll...

Boasting a great location in the Truman Annex, a shared pool, and easy beach access, you won't have to go far to dive into the beachside fun! Less than a mile to the picturesque Mallory Square and just under a mile to Fort Zachary Taylor Historic Park, there will be no shortage of attractions to...

Blue waters, warm winds, and the Florida sun await when you book a stay in this delightful two-bedroom condo with a private patio and heated community pool! Conveniently located just a few minutes from the Key West International Airport, this rental is part of the beautifully landscaped Sunset...

Make those dreams of a beach getaway a reality and book your next Florida vacation at this luxurious Key West condo. With upscale resort amenities like a shared pool and hot tub, tennis courts, a fitness center, and a covered parking space, your vacation will be packed with tropical excitement from...

Pamper yourself with a stay in this luxurious and sunny Key West condo. Surrounded by beautiful tropical landscaping, and boasting resort amenities like a pool, hot tub, tennis courts and a private balcony with views of the Salt Ponds Preserve, this comfortable rental will have you relaxed and...

Leave your troubles behind and head for the beach with this delightful and dog-friendly Key West condo! Incredible amenities like a shared pool and hot tub, tennis courts, and a private balcony with views of the marsh ensure you'll have a vacation to remember. Located in the upscale Sunrise Suites...

Gather your group at this festive property, home to three private hot tubs, deck space, multiple kitchenettes, and six bedrooms for up to 24 people. The family dog is also welcome to join you for an additional nightly fee. You're about a block away from Southernmost Point, a photo-friendly...

Relaxation will come easy at this studio condo in Key West. With a calming interior, entertainment, and an awesome location with a private parking spot (with off-street parking) close to all the action, this getaway will be one to remember! Located in a historic building just one block from...

Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed for a small nightly...

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,...

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...

Located right in the heart of Key West, this tastefully-appointed, tropical sanctuary comes with a private swimming pool, enclosed yard, and room for up to six guests. The family dog is also welcome to join you for an additional nightly fee. Take a stroll down to Duval Street and enjoy the many...

One of the most in-demand rooms at the Garden House Bed & Breakfast, the Royal Poinciana feels secluded thanks to its private patio and its quiet location at the end of the house. It's perfect for a couple on a romantic retreat or a solo traveler hoping to enjoy some peace and solitude on their Key...

Vacation in the heart of Key West when you stay at the beautiful Garden House Bed & Breakfast. With room for two, a private bathroom, and access to a shared heated pool, this charming suite is a dream come true for a couple seeking a romantic retreat or a solo traveler who wants to see the best of...

Your loved ones deserve to rest and relax under some Florida sunshine. Give them the vacation they deserve with this dog-friendly Key West condo with shared amenities like a pool and a hot tub. Courtesy Shuttle available to condo from airport and ferry terminal. A private parking spot is...

A fun-filled Key West getaway for two starts with this lovely room in the historic Curry House Bed & Breakfast. Cozy and comfortable, the room includes access to a shared pool as well as a semi-private balcony, which faces the street toward the front of the home. Curry House is located in a quiet...

Heron Suite's hot tubs access, back patio space, and proximity to the beach set the tone for a lovely stay in Key West's historic district! Well-outfitted for a couple's getaway, this suite offers an excellent location paired with the amenities of home. The family dog is also welcome to join you...

Cozy and compact, this recently renovated attic room in the historic Curry House Bed & Breakfast is perfect for two guests traveling on a budget. This room includes access to the shared backyard pool, air conditioning, and typical home comforts - everything you need for the vacation of a lifetime....

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...

Perfect for a romantic getaway or a small family vacation for four, this adorable Key West studio with side-by-side beds offers a shared, heated pool, outdoor seating and dining areas, and a well-maintained courtyard. This home also offers private parking for an additional fee. Just a couple of...

Absolutely ideal for a romantic getaway for two, this cozy studio offers a well-equipped kitchenette, a furnished deck, and access to a shared swimming pool at the heart of a beautifully-maintained tropical courtyard. Located just a block from Duval Street, the hottest street in Key West,...

This dog-friendly Key West gem offers a palm-covered patio and grill area, a kitchenette, free WiFi, and street parking! Plus, you're walking distance from the beach, historic landmarks, and local dining. Walk a half mile to the beach and enjoy Key West's legendary white sand and turquoise water!...

If you're planning a Key West vacation for yourself or your sweetheart, you can't go wrong with this charming suite in the heart of the city. Whether you're lounging by the shared pool, soaking up the sun on the semi-secluded second-floor sun deck, or relaxing in your room, you're sure to enjoy...

Experience Key West from the comfort of this cozy beach suite, complete with a kitchenette, private bathroom, and sleeping space for two. Your convenient location in the heart of Old Town makes this a wonderful couple's getaway! Walk over to Zachary Taylor State Park and Beach for glimpses of...

Here in the heart of historic Key West, you'll have access to a shared hot tub, dog-friendly accommodations, and grill on your backyard patio area, as well as private parking! From here, you're only two blocks from the beach at Fort Zachary Taylor State Park. Duval Street's restaurants, bars, and...