Eccentric, edgy, and enthralling—the captivating Key West is a lovely tropical oasis. Art galleries, craft boutiques, Caribbean villas and homes, tropical and lush green vegetation, and jaw-dropping sunsets that are a feast for the eyes rule the roost here. There are many things to do in Key West at night too. However, it might come as a surprise, but this city does not have sprawling luxury resorts but quaint mid-sized accommodations, such as cottages and cabin rentals, to complement its easygoing draw and vibes. For a really great base to explore the island and tune in to its charm, cottages are the way to go. Read on to find out about the best cottages in Key West, Florida.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.
1. Bright and sunny cottage for two (from USD 179)
If you’re looking to lighten up the mood, book your stay for a few nights in this charming cottage in the Keys. Bright colours and tropical plants accentuate the home’s exterior, creating a pleasant sight after an eventful day out. Able to comfortably accommodate couples and solo travellers, the sunny cottage features a well-appointed living area, a small yet functional kitchen, and a tidy bedroom with an en suite bath.
There’s a patio with comfortable lounging chairs by the front entrance, and the shared outdoor grill is available for use. The rental is also complete with air conditioning, Internet access, and a dog-friendly policy. Moreover, it’s just a stroll from Key West’s best restaurants and Duval Street.
2. Historic tropical cottage (from USD 492)
This tropical cottage for rent in the Florida Keys shares an interesting history, having been first built as a cigar maker’s cottage back in the early 1900s. Today, it has been delightfully refurbished to provide modern comfort for guests visiting Key West, with modern features such as flat-screen TVs and a backyard hot tub ready for use. Its cosy bedrooms boast spacious beds and tasteful decor. Looking for more sleeping options? You can convert the sitting room sofa into a sleeping space too.
Duval Street’s many popular establishments are within walking distance, and so is the community swimming pool if you want to dip your feet into the water after strolling around.
3. Lovely dog-friendly cottage in southern Key West Historic District (from USD 442)
Don’t want to leave your furry friend alone at home while you go on vacation? Pay a small fee and go on a holiday with them when you stay in this two-bedroom beachfront cottage in the Keys. It’s in a quiet residential neighbourhood in the southern Key West Historic District and features a fun shared pool. The rental is also fitted with a queen and two twin beds along with a sofa bed, comfortably accommodating six people.
A fully equipped kitchen, free Wi-Fi, a beautiful balcony and patio, and a lively barbeque grill for searing fresh seafood plunge you right into Key West mood. What’s more, the place is just five blocks from Higgs Beach Pier and a short walk to Duval Street’s many pubs, bars, and restaurants.
Top guest reviews
Amenities & Room:
beds were comfortable and the outdoor space was perfect for my familyvery pretty cottage and poolperfect size cute cottage with nice pool area and bbq grillCleanliness:
clean cottage and serviced wellthe house was very clean and well furnishedclean house witk wverything you would needthe apartment itself was very clean and appeared to have been renovated recentlyloved our stay at this cottage everything inside was nice and clean pool was cleanHost:
the host is very helpfulwonderful kitchen and friendly staffgreat communications from host good location clean stylish and comfortableRead more reviewsLocation:
fabulous location well equipped and cute comfortable placeexcellent cozy house great location easy walk to duval streetgreat location for walking to the beaches and downtown areasgreat location very close to duval street and a 5 minute walk from the southernmost pointthis place was very nice and the location was within walking to everything
4. Mint-green seaside conch-cottage oasis (from USD 203)
This custom-crafted, oh-so-sweet typical Key Westian conch cottage in the heart of Key West Historic District, hidden in a quiet lane, is just what the doctor ordered. What’s more, the four-bedroom haven is just a few blocks from the center of all entertainment and action in the island—Duval Street. With one king, two double, and two single beds, perfect for eight people, the cottage boasts an open-plan space with a living room, a dining area, and a modern fully stocked kitchen. A second comfy living room features flatscreen cable TV, there’s a well-stocked library for bibliophiles, and the house also has free Wi-Fi. An outdoor patio with alfresco seating opens to a private backyard with lounge chairs and even a fabulous new outdoor shower!
Top guest reviews
Host:
the neighbors were nice and friendly the house is beautiful with a pooldefinitely felt like home away from homeRead more reviewsLocation:
the location is also great to walk around town and get to duval stgreat place to stay lots of nice cafes and places to get food near by
5. Charming room in quaint one-storey cottage (from USD 204)
If you’re looking to rent a room rather than an entire home, this charming bedroom with a double bed in a quaint cottage in the heart of Old Town Key West is ideal. Not only is the home a mere 10-minute walk from Higgs Beach, but it’s also just a few blocks away from Duval Street and all shopping, dining, and entertainment in Key West. The clean, secluded room is located on the ground floor of a single-storey cottage, which also allows guests access to a full kitchen, a small fridge, Wi-Fi, a beautiful outdoor patio with a lush tropical garden and a swimming pool, as well as beach chairs. What’s more, bicycles for rent to explore Key West can be delivered right to your door!
Top guest reviews
Amenities & Room:
a ceiling fan and/or air conditioner kept the room comfortable day and nightwe loved the patio with the coffee bar mini fridge and poolthe outside area was very nice with small pool a fridge and coffee maker to usethe deck garden and pool area are so beautiful and nicely decoratedit was very comfortable and we especially enjoyed the outdoor coffee stationCleanliness:
very clean quiet spacevery clean and stylish placethe room was clean and comfortableeverything was clean which is most important to usthe room is clean and well decoratedHost:
our host claire was very welcoming and knowledgeablethe hospitality shown by our hosts was beautifulhosts were greatceline was a wonderful hostour hosts were very friendly & helpfulRead more reviewsLocation:
great location—next to all major attractions; close to duval stgreat location walking distance to a lot of placesnice room in walking distance to everythinga very nice space located within walking distance to duval stthis place was perfect the location was close enough to everything yet far away from noise
6. Smart two-bedroom cottage (from USD 378)
In the heart of the Old Town, halfway between the beach and entertainment-and-action-central Duval Street, this two-bedroom cottage rental in Key West, Florida is the ideal smart vacation home. The two-bedroom cottage features one super king bed, three sofa beds, and two single beds, easily accommodating six people.
There is a modern full kitchen for whipping up anything from quick to elaborate meals, cable TV, free Wi-Fi, a barbeque space, restaurant and weather suggestions and updates from Alexa, and even a family pass to Ft. Zachary Taylor State Park beach, which is nearby. Curl up with a book, music, or a cold one on the hammock located on the huge back patio.
7. Cosy Key West conch cottage (from USD 399)
The name says it all—Casa Serendipity is a fortuitous delight and the perfect blend of modernity and quintessential tropical charm. Located in the northern part of Old Town Key West, this three-bedroom cottage is close to Historic Seaport as well as all the best things that the town has to offer on Duval and Frances streets. Featuring Key West’s typical conch-cottage architecture and design style, this cosy two-storey island home is furnished with one queen and two king beds, a fully equipped modern kitchen for whipping up food whenever you feel like it, a spacious living area with a flatscreen TV for entertainment, and a six-seater dining table along with bar seating. A wraparound porch, a private pool area with comfy chaise lounges, and a barbeque grill complete the picture of perfectness that Casa Serendipity is.
Top guest reviews
Amenities & Room:
porch deck & pool outstandingmy favorite morning and evening ritual was a dip in the private black bottom poolthe kitchen is very well furnished including sharp knivesCleanliness:
everything was spotless and comfortableit was very clean and we were provided with plenty of toiletries and towels including pool towelsvery clean home and great kitchen/living room space loved itit was a wonderful clean house in a great locationHost:
we were greeted by greg who was so warm and accommodatingRead more reviewsLocation:
beautiful home and great location
8. A charming cottage in Old Town Key West
Conveniently located at Key West’s Old Town, this charming cottage lets you stay at the heart of the city. In the cottage itself, there are two bedrooms and two bathrooms that up to four people can share. A kitchen to cook in is also available for guests to use. If you’re working on the go, a workspace and free Wi-Fi are provided for your use. On top of that, the interior of this cottage is bright and cheerful, adding to the fun of your stay in Key West.
Key West, Florida, United States
281 meters (0.2 ft) from The Hemingway Home and Museum
9. An amazing seaside cottage
If you think staying at a cottage can’t be luxurious, think again. This awesome seaside Key West cottage for rent has interiors that look cosy yet chic and sophisticated at the same time. It has one bedroom and one bathroom, but it’s spacious enough for up to four guests. The kitchen is available for guests to use, as well as a workspace and Wi-Fi for workaholics on the go. To top that all off, there’s a private pool located in this property that you and your companions can enjoy.
Key West, Florida, United States
247 meters (0.2 ft) from The Hemingway Home and Museum
10. An elegant cottage
If you’re looking for space, this rental is the place to check out. Having three bedrooms and two bathrooms, this place can sleep up to eight guests at a time. Guests here can use a fully-equipped kitchen that can cater to all of their cooking needs. All bedrooms also come equipped with flat-screen TVs, and Wi-Fi access is available throughout the property. Apart from that, this cabin in Key West also has a private pool where you can swim in or just lounge around.
773 meters (0.5 ft) from The Hemingway Home and MuseumSuperhost
Accommodates: 8
Knockout Key West
Whether you want to soak in the sun in any of the scenic resorts up north, enjoy the livery of Duval Street, or explore the neighbourhood of Sunset Key, these cottages are guaranteed to make your vacation in Key West a memorable one. So, book one of the rentals above today!
Frequently asked questions about the best cottages in Key West, Florida
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