Top 5 Cottages In Key West, Florida

cottages in key west

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. It might come as a surprise, but this city does not have sprawling resorts but quaint mid-sized accommodations and cottages 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 these amazing and pretty-as-a-picture top cottages in Key West, Florida.

1. Lovely dog-friendly cottage in southern Key West Historic District (from USD 606)

Don’t want to leave your furry friend alone at home while you go on vacation? Pay a small fee and go on a Key West holiday with them, then stay at this 800-sq. ft. (74 sq. metres) two-bedroom cottage in a quiet residential neighbourhood in southern Key West Historic District. Featuring a fun shared pool, this space is 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.

Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
74 reviews  Wifi Available
Entire cottage 4 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
beds were comfortable and the outdoor space was perfect for my family
very pretty cottage and pool
perfect size cute cottage with nice pool area and bbq grill
clean cottage and serviced well
the house was very clean and well furnished
clean house witk wverything you would need
the apartment itself was very clean and appeared to have been renovated recently
loved our stay at this cottage everything inside was nice and clean pool was clean
the host is very helpful
wonderful kitchen and friendly staff
great communications from host good location clean stylish and comfortable
fabulous location well equipped and cute comfortable place
excellent cozy house great location easy walk to duval street
great location for walking to the beaches and downtown areas
great location very close to duval street and a 5 minute walk from the southernmost point
this place was very nice and the location was within walking to everything
Read more reviews

2. 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.

26 reviews Superhost  Wifi Available
Entire cottage 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
porch deck & pool outstanding
my favorite morning and evening ritual was a dip in the private black bottom pool
the kitchen is very well furnished including sharp knives
everything was spotless and comfortable
it was very clean and we were provided with plenty of toiletries and towels including pool towels
very clean home and great kitchen/living room space loved it
it was a wonderful clean house in a great location
we were greeted by greg who was so warm and accommodating
beautiful home and great location
Read more reviews

3. Seaside mint-green conch-cottage oasis (from USD 180)

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!

Oasis in old town Key West - private heated pool!
Key West, Florida, United States
7 reviews Superhost  Wifi Available
Entire cottage 5 Beds 6 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
the neighbors were nice and friendly the house is beautiful with a pooldefinitely felt like home away from home
the location is also great to walk around town and get to duval st
great place to stay lots of nice cafes and places to get food near by
Read more reviews

4. Charming room in quaint one-storey cottage (from USD 253)

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!

Old Town - Room Opens to Pool and Garden
Key West, Florida, United States
402 reviews Superhost  Wifi Available
Private room in home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
a ceiling fan and/or air conditioner kept the room comfortable day and night
we loved the patio with the coffee bar mini fridge and pool
the outside area was very nice with small pool a fridge and coffee maker to use
the deck garden and pool area are so beautiful and nicely decorated
it was very comfortable and we especially enjoyed the outdoor coffee station
very clean quiet space
very clean and stylish place
the room was clean and comfortable
everything was clean which is most important to us
the room is clean and well decorated
our host claire was very welcoming and knowledgeable
the hospitality shown by our hosts was beautiful
hosts were great
celine was a wonderful host
our hosts were very friendly & helpful
great location—next to all major attractions; close to duval st
great location walking distance to a lot of places
nice room in walking distance to everything
a very nice space located within walking distance to duval st
this place was perfect the location was close enough to everything yet far away from noise
Read more reviews

5. Smart two-bedroom cottage (from USD 360)

In the heart of Old Town Key West, halfway between the beach and entertainment-and-action-central Duval Street, this two-bedroom cottage 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.

A Touch of Bermuda in Key West
Key West, Florida, United States
5 reviews  Wifi Available
Entire cottage 9 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
jack is an extremely helpful and responsive host
Read more reviews

Knockout Key West

Make your Key West vacation a memorable one by staying at one of these gorgeous, utterly “Key Westian” cottages in the historic part of town.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Freelance writer. Coffee-lover. An expert at Kopfkino. Loves discussing New Zealand, domino theory, dystopian fiction, & Harry Potter.

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