Poolside Retreat 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...

Atlantic Ocean View 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...

Flamingo Hideaway 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...

Keepin' it Reel *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Enjoy the privacy that this waterfront condo has to offer during your next vacation to Key West. This condo is perfectly situated off...

Sunrise Suites - Saint Lucia Suite 201 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. Enjoy bird watching at the Salt Ponds Preserve from the comfort of your private balcony. Back at...

Sunset Marina Retreat *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. This waterfront condo, located within a gated community, boasts incredible views of the water and spectacular sunsets. With a...

Dreaming of a quiet tropical vacation in a luxurious town home with an equipped kitchen? Our residence is the place for you! Offering a relaxing location away from the hustle and bustle, our guests will enjoy access to three outdoor pools, daily breakfast, housekeeping, air conditioning, and more...

A Key Escape 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...

Dreaming of a quiet tropical vacation surrounded by palm trees? Our residence is the place for you! Offering a relaxing location away from the hustle and bustle, but close enough to partake in all the activities that Key West has to offer, our guests will enjoy access to three outdoor pools, daily...

Spend your holiday amid luxury when you stay in our suite that has a spiral staircase, a large private courtyard, original artwork, and air conditioning. Offering a relaxing location away from the hustle and bustle, our guests will enjoy access to three outdoor pools, daily breakfast, housekeeping,...

Dreaming of lazing in a hammock surrounded by palm trees? Our residence is the place for you! Offering a relaxing location away from the hustle and bustle, our guests will enjoy access to three outdoor pools, daily breakfast, housekeeping, air conditioning, and more when they stay here. • 2 Queen...

Bahama House Privacy meets convenience at this beautiful Key West vacation rental, which features a two-bedroom, two-bathroom home, a separate studio cottage, a private pool, and room for up to eight guests. The family dog is also welcome to join you for an additional nightly fee. This recently...

Sunrise Suites - Cozumel Suite 112 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...

Sunrise Suites - Tahiti Suite 104 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...

Sunrise Suites - Bimini Suite 211 This two-bedroom, two-bathroom suite allows you to show your friends and family the Florida getaway they deserve! Whether you want to explore the beaches or simply relax by the pool, all of Key West's wonders are out there waiting for you. When you've toweled...

Sunrise Suites - Samana Cay Suite 405 Immerse yourself in the laid-back ambiance 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...

Commodore's Compound 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...

The Galleria - Andy's Attic 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...

Sunrise Suites - Saint Martin Suite 207 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. A private parking spot is provided for your convenience....

Flagler's Crossing *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views,...

Conch Cottage *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Enjoy this classic Key West cottage featuring a shared pool and a furnished patio, located within blocks of beaches, shops,...

Secret Garden 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...

Truman * Duval - Studio A 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...

Banana's Foster Guesthouse 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,...

Tropical Village Hideaway 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....

Sunrise Suites - Rum Cay Suite 304 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...

The Frontier Flat 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...

Lazy Lane at Shipyard Condos 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...

Old Town Garden Villas - Bermuda Suite 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...

Old Town Garden Villas - Andros Suite Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style. Notice:...

Banana Breeze * Key Cove *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Escape to Key West and stay in this lovely waterfront home for a luxurious getaway. Your group will enjoy a private pool, a...

Sunrise Suites - Tierra Bomba Suite 403 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...

Old Town Garden Villas - Little Havana Suite 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!...

The Frontier Suite *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. 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...

Seaport Suite 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 make full use of the back patio space. You're right around the corner from Duval Street's...

Sunrise Suites - Margarita Suite 305 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....

Sunrise Suites - Big Kahuna Suite 202 Spend your next Key West vacation at this lovely condo in the Florida Keys. This rental comes equipped with a shared pool, hot tub, and tennis courts, along with central air-conditioning, a private balcony, and a fitness room. What's Nearby: This condo...

Papa's Hideaway #3 - For Whom the Bell Tolls Enjoy that next romantic getaway in Key West at this adorable and colorful ground-floor studio complete with a well-equipped kitchenette and view of the well-maintained courtyard and shared heated pool. Please note that off-street parking is available at...

Barefoot Bungalow This gorgeous home is a perfect escape for a private and quiet getaway. The home is surrounded by palm trees which creates a shaded and private patio. The home has a large 750 square foot master suite that is super luxurious- you may not want to leave the bedroom! A fully stocked...

Poolside Getaway *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Enjoy the unbeatable location of this two-bedroom, dog-friendly Key West townhouse. This home features four covered balconies,...

Curry House Room 5 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...

Casa Havana * Duval Square R22 Find a cool, comfortable retreat at this dog-friendly Key West condo, a well-equipped getaway with a private deck and balcony, access to a community swimming pool, and a wonderful location near the heart of the old town. This condo sits among tropical gardens in...

Duval Square Penthouse R19 Surround yourself with the historic charms of Key West at this dog-friendly penthouse, a spacious South Florida escape with a private hot tub, a deck and balcony for evening cocktails, and access to a lovely community swimming pool. You'll find this comfortable condo...

Bliss 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...

Heron Hideaway Surrounded by possibilities for fun and relaxation, this Key West cottage offers up to four guests the chance to bask in the warm Florida sun. Featuring a private hot tub, pristine seasonally heated shared pool, and easy access to a wide range of local attractions, this home puts you...

Sunset at Harbour Place Enjoy this spectacular condo with an oceanfront view of Key West harbor for your next getaway in the Key West! Located in Truman Annex, this home boasts beautiful water views from the balcony and all around the condo, you'll be sure to feel inspired during your stay! This...

Yellowfin Ledge On Duval 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...