Key West is a city in Florida about 145 km (90 miles) from the north of Cuba. It’s famous for its stunning sunsets, unique houses, and beautiful coral reefs. Did you know that it’s one of the top honeymoon destinations? It’s not hard to understand why. There’s the breathtaking views at Sunset Pier to take in, luxury boat tours to embark on, and adult-only hotels available for booking. But even if you’re not heading for a honeymoon but a family trip with your significant other or pets, Key West has lots to offer. Read on if you’re keen to find out some of the top pet-friendly vacation rentals in Key West, Florida.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and pet-friendly rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 09, 2024.
1. Homey unit near Smather's Beach (from USD 147)
Enjoy the convenience of this condo’s accessibility to the island’s attractions and the natural beauty of nearby Smather’s Beach. Perfect for a family or couples with all the comforts of home. Enjoy some entertainment and recreation, like swimming in the pools or playing tennis within the complex. In addition, you get one free parking spot right outside your corner unit.
You can bring a maximum of two cats or dogs weighing less than 50 pounds (22.65 kilograms) each, but you’ll need proof of current vaccinations. Enjoy a walk with your dog in one of the sections of the property for a fun experience.
Top guest reviews
Amenities & Room:
it had noodles for the pool but beach chairs would have been nicenice pools and laundry facility on the propertythe pool is perfect and there is plenty of outdoor spaceHost:
the owner was helpful and communicativewe had a such a great time michelle is a fantastic host very responsive and made everything easyRead more reviewsLocation:
excellent location awesome facilities would definitely stay here againi have already booked a return next year just a wonderful location and friendly people abound
2. Thirsty Mermaid (from USD 346)
Located in Casa Marina, this two-floor property will give you a warm and bright environment during your stay. With its four bedrooms it can accommodate up to eight guests.
After a full day of exciting activities, you may take a break and unwind on the balcony or take a dip in the heated and private pool. There’s also free onsite parking, making it convenient for anyone driving to the property. On top of everything else, you are welcome to bring your furry friends at a non-refundable cost of 200 USD per pet.
Top guest reviews
Amenities & Room:
the pool was heated and wonderfulCleanliness:
the place was clean and very accommodatingthe vacation rental was very cleanthe property was nice and clean and the pool was great fun for the kidsthe house is so well equipped very spacious clean and all amenitiesHost:
rating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulRead more reviewsLocation:
i was very happy with the locationi was very happy with the locationi was very happy with the locationi was very happy with the locationi was very happy with the location
3. Well-located apartment with a balcony (from USD 150)
This homey apartment is conveniently near Duval Street, where you’ll find a wide variety of entertainment options, including live music, bars, restaurants, and shops. Bring along some of your close friends and family members since it can comfortably accommodate up to four guests, and pets are also welcome.
This property offers a queen-size bed in the loft bedroom. In the living area, a full-size sofa sleeper and a 40-inch cable TV provide the perfect combination of comfort and entertainment. Have some coffee and personal reflection on the balcony to get your day started.
Top guest reviews
Read more reviewsCleanliness:
a clean and comfy setup with a very comfortable bed
4. Tropical-themed home with a swimming pool
Since this tropical-themed house is in a prime location, you’re near many iconic attractions. If you enjoy a day in the sand, head to Southernmost Beach and have fun swimming in the blue ocean water. Try out as many delicious meals in trendy restaurants or party with other people in nightclubs.
After a day of fun, come back to this house to take a break. Lounge on the sofa to watch a movie or show on the television. Go for a swim in the pool. When you’re hungry, prepare a hearty meal in the kitchen.
If you have a dog, you can bring them here. Just keep in mind that breed and weight restrictions may apply, so it’s best if you talk to the host first.
5. Charming abode near Higgs Beach
This charming house features four beds and an extra sofa bed in the living room, so all in all, up to eight people can sleep here. Aside from the number of beds, you can also find a complete kitchen for your meals. When it comes to entertainment, you can watch movies and shows on the television or splash around in the outdoor pool.
Higgs Beach is just a short walk away, so you can head there for a fun day swimming in the ocean or lounging on the sandy shores. For more fun, don’t hesitate to bring your beloved pets. Just make sure to let the host know in advance.
6. Bright and airy house with an al fresco dining setup
This ocean-inspired house features a king-size bed and a queen-size. But there’s also a pull-out double bed in the living room, so up to six people can be accommodated here. This makes the rental best suited for mid-sized groups, especially families and friend hangouts. You can also find a television, DVD player, and WiFi access here, so you can host movie marathon nights with your companions.
The outside area is just as wonderful. There’s an al fresco dining setup where you can the delicious meals you prepared in the kitchen. If you’re in the mood, you can also go for a refreshing dip in the pool.
If you have a pet, you should bring it here with you since this place is incredibly pet friendly.
7. Relaxing haven with a hot tub
Located in the Seaport neighborhood of Key West, this house is near several iconic sights. So, don’t waste your chance to stop by some of the trendiest restaurants in the area or enjoy the dazzling sunsets at Mallory Square’s nightly festival. You might also want to spend some time on the beach, sunbathing on the sand or swimming in the ocean.
After a day of fun, return to this rental to get your much-needed break. You can go for a refreshing swim in the pool or soak in the hot tub to soothe your worn-out muscles. There’s also a space for yoga if you’re into that. When you’re hungry, whip out something delicious in the kitchen.
This rental can accommodate up to eight people, making it ideal for groups. You’re also allowed to bring pets for more fun.
8. Tropical house with a refreshing pool
A fun-filled vacation awaits you in this tropical-themed getaway in Key West. There’s a spacious balcony where you can lounge during lazy days, simply sipping your favorite coffee while enjoying the fresh breeze. You can also swim in the pool whenever you want. If you’re visiting during winter, you can request the pool to be heated. When you’re hungry, head inside and prepare a hearty meal in the fully equipped kitchen. WiFi access and television are also available.
With four beds, this rental can sleep up to six people, making it perfect for groups. It’s also pet friendly, so feel free to bring your furry friends on this vacation for more fun.
9. Peaceful house in a beautiful garden setting
This house is nestled in a garden setting, making it the perfect destination for people looking for peace and serenity. You might want to start your day with a cup of coffee in the garden, enjoying the fresh air and the view. You can also swim in the pool to be refreshed or hang out with your companions on the loggia. When you’re hungry, feel free to cook delicious meals in the kitchen.
You should also not miss the chance to visit a few attractions. This house is wonderfully located in Key West, so you’re only a short walk away from restaurants, cafes, and museums. For trips to the faraway corners of Key West, head to the bus stop, which is just a short walk away.
If you’re planning to bring your dog, please show the host the proof of vaccinations and neutering.
10. Charming cottage with a private deck
With two beds and an extra bed in the living room, this charming cottage can accommodate up to six people. Additionally, you can find a sitting room connected to the living room, and this is the perfect place if you just want a quiet alone time with yourself. The kitchen is fully equipped, so feel free to whip out all the delicious meals that you want.
The outside area is just as marvelous. There’s a pool with a waterfall, as well as a deck where you can sit back and relax. With all these features, this rental is best suited for families or friend hangouts. Pets are also welcome here on a case-by-case basis, so make sure to contact the host beforehand.
11. Beautiful five-bedroom house located near Bayview Park (from USD 668)
Guests who have gone before you have highly spoken about this beautiful five-bedroom house. You will be situated near Bayview Park so you can easily take your pets on walks. There are two master suites and three common bedrooms. You may choose to enter the master suite via a private entrance. There’s a little garden area with an outdoor seating area by the private pool where you can chill with your pets. At night, have them sleep on the couches in selected bedrooms.
Top guest reviews
Amenities & Room:
the rooms and furnishings gave off a great vibehuge comfortable bed in a studio with lots of natural lightthe room itself was air-conditioned on arrival and decorated very wellthe place is comfortable clean and updated with stylish furniture decoration and amenitiesthe cuban coffee a couple doors down at the laundry mat is deliciousCleanliness:
clean and spacious suitesshawn’s place was great very clean and stylish and the bikes were awesome to get aroundthe bed was comfortable and the apartment was well-appointed and spotlesssuper cozy and clean very nice locationstudio blu was well decorated comfortable and cleanHost:
shawn was a wonderful hosthe was a great hostshawn was an excellent hostshawn was a great host with good recommendations for key westshawn is really helpfulRead more reviewsLocation:
it’s close to everything and the neighborhood is safe and quietthe location was perfect for us for walking or biking to many main attractionsyou can walk or bike to all of the main attractions key west has to offerthe blu suite is an ideal place to stay for any couple staying in key westthe most stunning room in an incredible location in old town
Superhost
12. Cozy suite with access to a heated saltwater pool (from USD 377)
This one-bedroom suite has a queen-sized bed and a sofa bed. It’s perfect for up to three persons and a pet. You will need to pay the host a pet fee to have your pet enter the premises. The living room also has a reading couch which makes a good resting place for your pets during the day or night. You may also access the heated saltwater pool from 8am to 10pm. There are lounge chairs and seating areas for you and your pets to chill at.
Top guest reviews
Amenities & Room:
the furnishings our upscale and the queen bed is so comfortablelittle extras like breakfast bars coffee water and creamer were greatly appreciatedthe pool area was so nice to sit an relax in completely private from neighborsCleanliness:
quiet neighborhood clean and private accommodationsapartment was clean very nicely decorated and had everything we could have neededHost:
the owner is so nice and an exceptional hostpj is extremely responsive and the host (larry) was available to answer any questionsbeautiful accommodations with the added bonus of a kind and attentive host—why would we go anywhere elselarry was an amazing host—full of local recommendations and committed to making our stay comfortable and relaxinglarry’s place is a hidden gem he was the best host and pj was so responsiveRead more reviewsLocation:
the location is ideal
13. Homey apartment close to USCGC Ingham Maritime Museum (from USD 450)
This apartment near the Key West Historic District reminds us of home. There are two bedrooms and one-and-a-half bathrooms. One of the bedrooms has a queen-sized bed while another has two single beds. There is also a sofa bed that can function as a bed for one person. Your pets can hang out at the private back porch or at the common pool area with sunbeds. Nancy Forrester’s Secret Garden is closeby for you to walk your dogs. Do note that there is an early check-out time at 10am.
Top guest reviews
Cleanliness:
it was spotlessly clean there were plenty of towels for both the condo and the poolwalter’s place was very clean with comfortable bedsthe pool was very cleanthe space is as advertised clean close to pool and great for a small family’sHost:
walter was an excellent hosta little unexpected issue (not the host’s fault) when we arrived but it was gracefully and quickly resolvedwalter was great to work with responded quickly to questions and was so helpfulRead more reviewsLocation:
the location is amazing; it’s walkable distance to everythingperfect location to everything but still quietgreat place within walking distance to about everythinggreat location easy walking to everything old town has to offerwonderful location to everything that key west has to offer
14. Romantic retreat with a private outdoor spa (from USD 395)
This studio is in the heart of the Key West Historic District. The bedroom has a king-sized bed with a little couch at the side for you to do some reading or for your pets to rest on. You will get a little kitchen corner fully equipped with various utensils and basic supplies. There is also a private outdoor spa with seating areas where your pets can hang out. While pets are welcome, do note that children and infants are not.
Top guest reviews
Amenities & Room:
cons:-wifi was pretty week inside the cottagepool deck area are beautiful great vegiatition gas grill and morewe loved the lush greenery and palm trees around the poolsroom was super clean and had everything needed including sun tan lotionCleanliness:
so clean and comfortableit was clean and quietperfect clean cozy and convenienta self-contained well-appointed room off the clean and clear poolrooms were very clean neat and the beds were very comfortableHost:
the staff is super helpfulstaff are the most customer focused and very helpfulthe staff was amazing and promptly took care of anything we neededthank you naomi for being a great hostawesome place with a great staffRead more reviewsLocation:
perfect location close to duvalthe location is perfectlocation was absolutely perfectthe location was perfectwe loved the location
15. Family-friendly house with a balcony (from USD 640)
There are three bedrooms in this family-friendly house for six guests. One has a king-sized bed while the other two rooms have queen-sized beds. The living room faces the see-through glass doors. You will get a spacious kitchenette with a dining table by the side for six people. You can have your pet sleep on the couch in the master bedroom. There is also a balcony attached to the master bedroom where you and your pet can get some fresh air while chilling outdoors.
Top guest reviews
Amenities & Room:
the furniture was comfortable and modernthe outdoor space was private and peaceful with lounge chairs a dining table and a grillalso an awesome back deck and kitchen for entertainingall the staples in the kitchen made for easy cookingthe beds are incredibly soft our favorite aspect was the private deck and yardCleanliness:
it was impeccably clean and maintainedit was very cleanhouse was sparkling cleaneverything comfortable and cleannice clean accommodations in a tropical setting even for key westHost:
the host was pleasant on point and attentive to our needsour host graciously let us check in earlymike was a terrific hostour host was easy to contact and very accommodating to our needsnice pool and helpful hostRead more reviewsLocation:
fantastic location walk anywherethe location was perfect and within walking distance to everythinggreat location that is both quiet but close to all the fun stuffthis house has a great location where you can walk everywheregreat location my family has visited kw for a very long time
16. Spacious three-storey house at The Meadows (from USD 1722)
This is your chance to house everyone under one roof. This is because there are five roomy bedrooms and four bathrooms. The entire accommodation can fit up to 12 people! Selected bedrooms also have couches to act as a bed for your pets. You will get your own private pool with sunbeds lining the side. The master ensuite bathroom also has a bathtub for you to give your pets a quick shower after some fun outdoors. Consider taking your pet to the small dog park located at 627 Grinnell Street.
Top guest reviews
Amenities & Room:
the air conditioning works great and we were very comfortable our entire visitthe beds were super comfortable and the mastereasy check-in nice kitchen large rooms plenty of spaceeach bedroom had a nice full bathroomthe house was amazing and plenty of room for everyoneCleanliness:
the house was very cleangreat large home as described clean and well maintainedit was as clean and roomy for the ten people that were in our groupHost:
the property mgr & staff were very friendlyrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulRead more reviewsLocation:
the location was perfectperfect location so we could fish off the dockit is close to most attractions and is about a 20 minute walk to duvall streeta perfect place for a gathering of family and/or friendscaptain's daughter was spotless in a great location quiet neighborhood that within walking distance to duval street
17. Awesome residence in the heart of Old Town (from USD 1215)
This accommodation for six to eight persons is situated steps away from Nancy Forrester’s Secret Garden. This garden makes a good place to walk your pets! You can also spend some time with your pets at the outdoor seating areas by the private poolside. There are also sofas and a couch for your pets to rest indoors. There are two rooms on the first floor and a loft. The loft rooms have two single beds that can be combined to form a king-sized bed. You will find a pet shop at 513 Fleming Street if you need to make quick purchases or grab some pet supplies.
Top guest reviews
Amenities & Room:
comfortable furniture beds and pillowsvery nice private yard / pool area with gas grillloved the heated pool at 1am/ 3amCleanliness:
the unit was spotless and is in a great areathe house was clean bed were comfortable and the pool was perfectionHost:
rating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was more than helpfulpet friendly was huge bonusRead more reviewsLocation:
great location to walk to duval but also to explore different neighborhoodsthis is such a cute place - well equippedperfect location for exploring key west totally private and very comfortable and cozyit was perfect for our short weekend trip and within walking distance of many attractions100% love the location n the heated pool
18. Unique stay with a cocktail pool (from USD 735)
This two-storey house with two bedrooms and two bathrooms is great for a family seeking a little privacy. There is one bedroom on the first floor with two single beds. The master bedroom and ensuite bathroom are on the second storey. We love the high ceiling in the living room, giving us the impression of a bigger space with better airflow. There is a sofa bed and couches for your pets to chill on. The glass doors open up to the outdoor patio with a cocktail pool. At the outdoor patio, you will find two loungers and outdoor seating areas where you can hang out with your pets.
Top guest reviews
Amenities & Room:
the furniture was comfortable and the home had everything we neededthe downstairs bedroom had a strong mold smell from the air conditioning unitthe dip pool was great for cooling off in the late afternoon before we went back outHost:
responsive & helpful staffrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulRead more reviewsLocation:
place is beautiful and location is centralnice place near enough to walk to the actionwhat a great location as wellreviewer comments:great location in old towni was happy with the location
19. Luxurious oasis with a hot tub (from USD 349)
This accommodation exudes a tropical vibe with palm trees at the entrance and various potted plants indoors. You will also spot various palm prints in different parts of the house. There are two bedrooms with queen-sized beds, a half bath, and a bathroom. You and your pets can hang out at the private deck with a hot tub, sitting area, and gas grill. Grooming By John, a pet groomer is situated just a short walking distance away.
Top guest reviews
Cleanliness:
very clean and well maintainedit was clean and nice the inside was newish and maintained well we would gladly stay there againaccommodations were clean and tidythe property was clean updated and in a great locationvery clean and spacious which is perfect especially if you will be staying for a few daysRead more reviewsLocation:
centrally located so it's close to most things if you like to walkperfect location and a great propertygreat large apartment close to duval street in key westthe place was really nice and located 1/2 nlock from duval so right where we wanted to bewe had a great week at this location
20. Fabulous residence a block away from Duval Street (from USD 548)
By staying at this two-bedroom and two-bathroom residence, you will be a block away from Duval Street and close to The Ernest Hemingway Home and Museum. There is a king-sized bed in the master bedroom, a queen-size bed in the second bedroom and a sofa bed in the living area for your pets to rest on. While pets are welcome, there may be certain restrictions. Do contact the owner before booking. You will also have full access to the pool and spa right outside the living room. Hang out with your pets outdoors without any worries! The nearest park is Nancy Forrester’s Secret Garden.
Top guest reviews
Amenities & Room:
we especially enjoyed the quiet of the courtyard pool areacool deck area to sit around pool with music decking gets super hotwe really enjoyed the privacy of the patio and poolthe kitchen facilities were adequate for all our cooking and the grill outside worked awesomevery quiet neighborhood and bed was comfortableCleanliness:
the house was clean and well maintained otherwisethe house is exactly as pictured & very cleanwe loved the layout of this property the house was clean comfortable and the pool area was very privateHost:
owner is very responsivedavid the owner very nice and responded to all questionsthe owner was very accommodating to our needs and the home was beautifulthe owner was easy to contact and was very helpfulthe owner seemed very nice in personRead more reviewsLocation:
location was the best partthe location of the property was perfectthe location made for an easy walk to the hemingway house butterfly conservatory and many nice restaurantsbeautiful property and nice and quiet in central part of the actiongreat place to stay
Find your ideal vacation rental in Key West
With a list of top pet-friendly vacation rentals to choose from, where will you take your pets to? You can choose the one close to Nancy Forrester’s Secret Garden since it offers a walk outdoors. If your pets are homebodies, then having a private porch or backyard is good enough. Travellers with big families should consider the beautiful five-bedroom house located near Bayview Park or the spacious three-storey house at The Meadows. As for couples, the romantic retreat at the studio cottage would do the trick. Have a wonderful vacation with your loved ones at Key West, Florida!
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