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Key West Pet Friendly Vacation Rentals
We offer Vacation Rentals: Book your Home securely here and save!
Stay steps from the sand in a Key West Home with Pets Allowed designed for convenience, coastal style, and those perfect Gulf sunsets — ideal for couples, families, and anyone who wants a seamless Florida Keys getaway.
Vacation Rentals by Owner in Key West Florida.
We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for places to stay in Key West.
To book a selected property, follow the "Search Availability" button or "View Rental" for Pricing & Rates, which will take you directly on our partner website. All bookings are securely completed on our partner websites.
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
DETAILS AND AMENITIES...
Enter this inviting open floor plan with incredible natural lighting throughout. Three sets of French doors take you from the living/kitchen space out to the outdoor entertainment area, consisting of a private heated lap pool all to yourself, propane gas grill, swing set, outdoor dining for 4, additional outdoor seating and pool loungers. Wood flooring, high ceilings and breezy ceiling fans in each room will keep you cool and refreshed on a sultry summer's day. Whip .......
10.0 Star Review
4 Bedrooms
- Sleeps 8
Key West Vacation Rental
Pet Friendly 
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. This two bedroom Villa Vista is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.
The number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West.
1/2 block to Hard Rock Cafe
Simonton Studio, an Old Town get-away for 2
The Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everthing you need to fix your own cocktails.
Located in a 6 unit compound this tiny Association is located in the heart of Old Town on Simonton St. Walk to the Hemmingway House, the Butterfly Conservatory and stroll Duval street with it's shops, restaurants, galleries and museu.......
Shady Palms - Stay In Comfort- May - Aug 10% OFF - 2BD/2.5Bath - Private Pool
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throughout the house to open up and let in the Key West sun. Relax in the living with a large screen TV or sit on the front porch to read a book and relax with the breezes or if needed, the porch fan. The kitchen is perfect to cook your fresh caught fish with enough room to seat four at the countertop.
The master has a queen bed with its own ensuite that has a shower with multiple.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Key West Vacation Rental
Pet Friendly
Superb Location, Affordably Priced
This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. This accommodation is the perfect location for exploring Key West. You can walk to the Hemmingway House, the Butterfly Conservatory and stroll Duval St with it's many restaurants, shops, galleries and museums. Come home to a king size bed, full kitchen and everything you need to make your own cocktails.
This newly redecorated Studio features a seating area , flat .......
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom Villa Porta is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. Please email us even if the availability calendar looks full.
The number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all thin.......
A Touch of Bermuda in Key West
Note: Minimum stay is 29 days / 28 nights. Saturday-to-Saturday bookings required. Exceptions made for special events including boat races and Fantasy Fest. Pets by special permission.
About This Property
A Touch of Bermuda is a privately owned Bermuda-style conch cottage in the Shipyard section of Truman Annex — one of only seven private townhomes available for rent in this gated, 24-hour secured community in the heart of Old Town Key West. This is not a cookie-cutter condo. It .......
Your own Private Resort! 50ft Dock on Canal w/ Pool, Tiki and RV Hookup!
Welcome to your private slice of paradise in the Keys! This exquisite waterfront home offers an unparalleled opportunity to immerse yourself in coastal luxury. Nestled on a sprawling 1/3-acre property, our retreat boasts breathtaking grounds and a mesmerizing ambiance that promises an unforgettable stay.
Highlights of Your Stay:
🌅 Spectacular Indoor-Outdoor Living: Soak in stunning bay views from our spacious patio deck, perfect for al fresco dining or simply admiring the gorgeo.......
10.0 Star Review
4 Bedrooms
- Sleeps 8
Key West Vacation Rental
Pet Friendly
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!
OLD TOWN CLASSIC...
This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding location of Southard and Ashe Streets, this upscale abode is just minutes from Duval's many restaurants and bars. You are within walking and biking distance to museums, shopping, and Fort Zachary Taylor beach. Come inside this bright and sunny retreat that boasts fully renovated baths and kitchen, wood floors, high ceilings, and Dade County Pine walls.
***PRIMARY GUEST MUST.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pet Friendly
SEA FOREVER ~ Downtown Ocean View Home w/ 3 BR, 3.5 Ba w/ Pool!
MODERN TROPICAL JEWEL WITH STUNNING OCEAN VIEWS…
This contemporary and spacious custom-built gated home will beguile your senses, luring you inside with the finest of amenities and stunning design. Just a stone's throw away from the infamous Southernmost Buoy, you are truly seated in the heart of paradise in this small gated community. Designer finishes and top-of-the-line fixtures can be found throughout and will soothe and spoil your inner pleasure-seeker. This vibrant and bustling area i.......
Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly
Welcome to our Key West retreat — a home we cherish and live in part of the year, now open for guests who appreciate comfort, character, and a lived-in sense of ease that you won’t find in a typical vacation rental.
Located just one block from the iconic Green Parrot Bar and two blocks from Duval Street, you’ll be surrounded by the best of Bahama Village — from Blue Heaven, Hemingway House, and Willie T’s to endless galleries, cafes, and music. Yet you’d never guess how close .......
10.0 Star Review
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pet Friendly
Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom Villa Rosa is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.
The number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West.
1/2 block to Hard Rock Cafe
2.......
A Touch Of Cuba In Key West
MINIMUM STAY 29 DAYS/28 NIGHTS
About This Property
A Touch of Cuba is a privately owned, two-bedroom, one-bathroom condominium in the Shipyard section of Truman Annex — one of Key West's most sought-after residential neighborhoods. Located on Southard Street, the main entrance to the Truman Annex, the property is within walking distance of Duval Street, the Ernest Hemingway Home, the Key West Butterfly Conservatory, and the island's best restaurants, galleries, and beaches.
This.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Key West Vacation Rental
Pet Friendly
THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w/ Pool!
WHERE LIFE IS PURE…
This dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West charm within its tranquil setting. Peacefully located with convenience to everything, this home truly has it all making your Key West love story one never to forget!
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS AND AMENITIES…
Pull up to the first floor of this island beauty showcasing lush, vibrant foliage surrounding this quaint abode. Step on.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pet Friendly
Old Town Beauty built in 1883
Enjoy the lovely Key West ocean breeze from your private Tree House. This is the quietest area of Old Town but only4 blocks to the beach, 3 blocks to Duval, you will not find a better or quieter location to enjoy all that Key West has to offer. Its less than 4 blocks to Blue Heaven, Santiago's, Moon Dog Cafe.
This storied and historic 1883 Conch home has been lovingly and thoughtfully renovated to perfection. Gleaming Dade County Pine floors and walls, period windows, period bath fixtures w.......
4 Bed House w/ Heated Pool and Dock - 4 Min. to Key West
- 28 Night Minimum Rental
- Private Heated Pool
- Private 65 Foot Deepwater Dock in Protected Harbor
- 10 Minutes by Car to Downtown Key West
- Open Floor Plan
- 600 Pound ice machine
- Chest freezer for bait
Dock your boat in the backyard and enjoy lagoon views from this family and pet friendly one story private home. Take advantage of the deep water access to both Atlantic and Gulf sides of the Keys. All of this just 10 minutes by car to downtown Key West........
10.0 Star Review
4 Bedrooms
- Sleeps 13
Key West Vacation Rental
Pet Friendly
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!
If you’re looking for a Florida Keys home that rivals the seaside homes found in ‘Coastal Living’ magazine, look no further! COASTAL LOVING is an inviting two-story private home that offers a relaxing vacation setting and comfortable accommodations. This easy living home combines a classic Key West design with the finest modern updates and conveniences. If you ever decide to pul.......
10.0 Star Review
4 Bedrooms
- Sleeps 8
Key West Vacation Rental
Pet Friendly
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!
It is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack dab in the middle of Old Town. SEAPORT SENSATION is one of the newly built breathtaking townhomes at Old Town Villas that allows you to enjoy the luxu.......
3 Bedrooms
- Sleeps 8
Key West Vacation Rental
Pet Friendly
Key West Beach House with heated pool, tiki, and dock.♿︎
Welcome to Key West. Located on this beautiful island 13 miles from downtown is this quaint 2-level beach home. With sleeping for up to 10 people, you can bring the entire family or your best friends to experience the beauty of the Lower Keys. While you are at it, don’t forget your Fur Babies and your boat!
Then as you step out on the deck you are only steps away from the Gulf of Mexico. You can relax on your private patio or enjoy the private beach with kayaks and paddleboards. The.......
9.6 Star Review
5 Bedrooms
- Sleeps 10
Key West Vacation Rental
Pet Friendly
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.
Two of the Queen bedrooms share an en-suite bath easily.......
ISLAND DAZE ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 block to Duval!
ALLOW THE PERFECT VACATION TO UNFOLD...
The epitome of laid-back, island living is found within this classic, Conch style home bringing endless charm to your tropical vacation. Steps from high end galleries, bars and restaurants, yet tucked away on a quaint and colorful lane, this home entails all the desired amenities that will truly immerse you into the Key West spirit.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS & AMENITIES...
A friendly front porch awaits your.......
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The Villa Grande is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. The number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West.
1/2 block to Hard Rock Cafe
2 blocks to Margar.......
Just Restored One Bedroom Hideaway with Garden and Hot Tub 5 No Need For A Car
This one bedroom apartment on the ground floor is completely restored with a full kitchen and laundry. This unit has everything you need for an extended stay.Walk out to the private garden from your living room. Located on one of the best streets in Old Town. You are just 3 blocks from the Harbor, home to the freshest seafood restaurant and the best happy hours on the island. Or Walk down to Duval street to experience the local music scene and bar hopping, restaurants and shopping. Located in a .......
10.0 Star Review
1 Bedrooms
- Sleeps 4
Key West Vacation Rental
Pet Friendly
PET FRIENDLY! Completely REMODELED! 3 Bedroom 3 bathroom home. Sleeps 8
"Flip Flop Inn" is a beautiful 3 Bedroom 3 Bath home, (each bedroom has its own private full bath), and a Queen size Futon. We're located in the luxurious gated safe community of Coral Hammock. The grounds are beautifully landscaped and include a large community pool and a fitness room. Two parking spots are also included in your rental. We are ideally located at mile marker 5 which is only a 10 min hop to downtown Key West, Duval St, and all the action. The Key West golf course is directly a.......
Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave
Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, coffee shops and bars with live music are all within walking distance. A pleasant 10 minute walk (0.5 miles) will take you to the bustling entertainment part of town located primarily along Duval St.
If you want to unwind and relax, lounge under the palm trees of the large pool located within this seven house gated community and soak in the Key West easy lifestyle you.......
Paradise found at the Key West Golf Club!
We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee or celebrate another amazing sunset with an evening cocktail on one of four open air decks surrounding this beautifully appointed townhouse in the prestigious Key West Golf Club. Located directly off a gorgeous, heated pool complete with a waterfall, this is your home away from home to spend your days relaxing, playing a round of golf, fishing, snorkeling and enjoying all that.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Key West Vacation Rental
Pet Friendly
Palm Trees Ocean Breeze Key West FL
Three bedroom, four bathroom private home with heated pool . Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition TV and surround stereo throughout the home. High Speed internet and faxing available as well.
High security inside: guarded and gated Truman Annex. Only three blocks to Jimmy Buffets, Sloppy Joes and Duval Street entertainment. One of the nicest homes in the best area of Key West. Watch sailboats and sunsets from the decks during the da.......
Peaceful 2 BR Condo with All Amenities
Enjoy the comforts of home in the midst of paradise.
Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, tennis court and Internet service. The unit is on the 3rd floor, accessible by elevator. Has completely equipped kitchen, 2 fully furnished bedrooms and 2 baths. Living room has sofa bed that opens to a queen-sized bed. Has private balcony overlooking the adjacent Sa.......
LOVE LANDING ~ Charming 3 Bedroom, 3 Bathroom Home w/ Pool and Parking!
MARITIME-INSPIRED LIVING…
Come unwind in this desirable retreat, tucked in a quiet and private lane just a stone's throw from all the excitement of Duval Street. Your location is ideal with swaying palm trees and gentle sea breezes all around. This upscale delight beckons you into your tropical haven beneath the twinkling stars of Key West. Allow your delightful island story to unfold.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS & AMENITIES…
The open concept fea.......
10.0 Star Review
3 Bedrooms
- Sleeps 8
Key West Vacation Rental
Pet Friendly
Old Town Historical Charm
A 3/2 home in the historic district of Old Town Key West with soaring ceilings and a ton of character. Walk to Duval, but nestled in a quiet neighborhood next to St. Mary Star of the Sea. Each bedroom features a private balcony. We believe the house was built in the late 1800’s. It was moved in the 30’s when the land it sat on was taken for use by the Navy. The land it originally sat on is where the post office is now near the corner of Fleming and Whitehead. The home features original Mia.......
3 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pet Friendly
~ INN COGNEATO ~Experience island life in a private oasis with heated pool.
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!
THE PROPERTY: Step inside the white picket fence and enjoy your private escape. Surrounded by lush greenery and palm trees, this home with modern amenities is tucked into a charming, historic neighborhood. From here you can walk to many attractions Key West is notable for including bars, restaurants, and shops. Snap a photo at the Southernmost Point marker or grab lunc.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Key West Vacation Rental
Pet Friendly
~ POINCIANA PARADISE ~ Casual duplex 2 blocks from Duval Street!
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished duplex home comes with Key West charm and contemporary touches. Walkable to many shops and attractions, you will feel like a local in no time. Only two blocks to Duval Street, you can relax and enjoy your time here, whether you select the upper or lower floor of this home.
The entire house includes a total of two bedrooms and two bathrooms. Each floor has a king bedroom, with brand new mini-split AC, an ensuite .......
10.0 Star Review
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pet Friendly
~ CASABLANCA GRANDE ~ Old Town quiet duplex with pool, hot tub, and parking!
THE PROPERTY: Enjoy fresh air and sunshine from your front porch, private pool or hot tub at Casablanca Grande. You are not far from the excitement of Duval Street in this home but far enough away to enjoy peace and quiet. This home consists of BOTH sides of a duplex.
This duplex is unpretentious and comfortably furnished. There is sleeping space for six via 2 king beds and a queen sleeper sofa. In addition, each bedroom has an ensuite bath with pedestal sink and walk-in shower. The livin.......
10.0 Star Review
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pet Friendly
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip in your pool. Whether you lounge in the cabana or enjoy dinner under the stars, this home has it all! Close to the sights and sounds of Duval Street yet quietly surrounded by Bougainvillea and palm trees, you will love this location. The fenced property with private pool has 4 bedrooms and 2.5 baths. It’s perfect for vacationing with friends or kiddos who will enjoy the secon.......
10.0 Star Review
4 Bedrooms
- Sleeps 7
Key West Vacation Rental
Pet Friendly
~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!
THE PROPERTY: As you enter the carport and begin to unwind, you will be greeted by beautiful porches and tropical greenery. Drop your luggage at the door and go for a swim. Around back, a private pool awaits you. Later, you can cozy up to a bedroom of your choice.
The first-floor queen ensuite bedroom includes a desk, dresser, ceiling fan and access to the pool.......
~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.
THE PROPERTY: This one bedroom, one bath, first-floor duplex is conveniently located in Old Town. Walkable to so many Key West activities, you won’t need a car, just a pair of sandals or a bicycle. Tucked down a quiet one-way lane, this casual home is comfortably furnished. It sits just a block and a half from Duval Street yet it’s oh so tranquil. As you enter the front door from your covered porch, you will be welcomed by natural light, sunny walls, and Florida furnishings. The living room .......