10 Vacation Rentals In Key West, Florida - Updated 2021

vacation rentals in key west fl

Key West is known for its crack of dawn-manner and early risers. It also has one of the largest barrier reefs in the world. It points all its arrows to the great varieties of water sports and the sunshine that is around all year long. Well, who doesn’t want to enjoy the tanning sun rays and the beaches on their trips anyway? The historic sites and its Duval Street, the stunning conch-style architecture, and the fun walking tours are the best to have an inclusive look over the island. You will love your rental for not only their modern designs but also their colorful gardens. Have a look over these amazing vacation rentals in Key West, Florida:

1. A remodeled antique (from USD 249)

This renewed 100+ years old cottage combines the features of a modernly furnished home and the history of the building. The rental house could accommodate 4 guests by providing them 2 bedrooms containing 2 queen beds and 1 bathroom. The spacious backyard is the best choice for enjoying your morning coffee and some nature; barbecue using their gas grill, and keep your pets secure. The home offers WiFi, TV, washing machine (plus dryer), linen change, a prepared kitchen with a dishwasher, a microwave, and cookware. It is a monthly rental house that is located in Old Town, which is just a walk away from Higgs beach, bars, restaurants, art galleries, and Duval Street.

Old Town Cottage in Paradise hot tub, dog-friendly
13 reviews Superhost  Wifi Available
Entire residential home 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
our family had a relaxing and very comfortable stay at ceres' charming historic conch house in key west
we loved the nice touches like the gas range and the beautiful shower
everything was seamless comfortable and clean
ceres was super helpful and responsive
ceres was very helpful in providing information both before our trip and when we arrived
amazing stay this property is positioned so that everything on the island is close
everything was as described and the location was convenient with parking opportunities right outside
the location was excellent and did not run into any issues during my time there
however there are plenty of free parking spots in the street
Read more reviews

2. A heaven on earth experience (from USD 172)

Bird of Paradise consists of 2 bedrooms, a living room, 2 washrooms, and could welcome 6 guests. While the master bed has a king bed and the 2nd room has a queen-sized bed, both include designed glass doors that allow the natural sun light in, a shower each, TV, fan, and a closet. The living room has a hidden queen bed in the dresser that folds open. A big heated pool, privately fenced backyard, and barbecue facilities are provided for a more fun evening. The amenities offered include a washing machine/dryer, AC and heating system, fans, linen change and towels, and WiFi upon request.

**BIRD of PARADISE** Elegant Home & Pool + LAST KEY SERVICES…
Superhost  Wifi Available
Entire residential home 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

3. Annex in Old Town (from USD 300)

The house contains 2 bedrooms that could be used by 4 guests. Each room has a queen bed, a private bathroom, a balcony to allow cool fresh air in, a fan, and a TV. A fully equipped kitchen, dining, and living rooms are great to prepare food, dine, and spend some quality chatting time with family or friends. Other provided facilities include air conditioning, washer and dryer, internet, parking, heater, outside swimming pool, and fireplace. An outside deck in the garden will allow you to enjoy a quiet relaxing afternoon. A short walk and you will reach Fort Zachary Taylor Beach, Mallony Square (for the best sunset view), or the well known Duval Street.

RENOVATED - Conch Get Enough! - Old Town's Truman Annex
Key West, FL, US
141 reviews
townhome 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The other bedroom has a full size bed and that room is fairly small
Kitchen has everything for cooking
The place was immaculate and very cozy
There are 2 bedrooms; one has a poster bed and is very comfortable
Parking is tight but we parked a full size SUV so it can be done
The place was very clean
This 2 bedroom 2 bath condo was very nicely furnished and very comfortable for 4 adults
He was equally as responsive
Some difficulty finding the unit; a map before arriving would have been helpful as well as a map to find our way in and out since there are a lot of walkways and several entrances
We even heard the lovely roosters every morning though 4am was a bit early
Upon check in we needed some new keys and she was quick to respond via phone and email and put us in touch with Alistair
property Owner persona lily reached out to introduce herself and was very thorough and timely with responses to any question I had Highly recommend
The location is good for the beach Little White House
We love staying in Truman Annex because it is close to everything but tucked away in a quiet gated community
There is really no shelf space (except tucked away in the closet) and no dresser
The proximity to downtown makes Truman Annex an ideal location
Everything was within walking distance for us restaurants bars
Read more reviews

4. A house of dreams (from USD 200)

This extravagant house has a lounge on the outside porch to enjoy the fresh air, a fancy restroom with a couples shower, a TV in the bedroom, maybe for a late night movie, free bicycles, and a washer and dryer set. Their french doors allow the warm sun rays to come in and let you enjoy the brilliant green palm trees from comfort.

Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
107 reviews
condo 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
The kitchen is well stocked with everything you might need
The kitchen and bathroom are very modern
Plenty of room and quiet off the parking areas
The beds were very comfortable
great condo kept in great conditionhighly reccomend
The condo is beautifully decorated and had everything we needed
Bed was very comfortable and patio was great with the fans
Sherri was helpful guiding us through our first trip to Key West providing us with information about the area
Sherri was wonderful to work with and very informative
and she was quick to answer all my questions
We walked everywhere even the beach
Sherri and Michael were very gracious hosts
The complex is in a great location quiet but a short walk or bike ride to the action in Duval or to the Fort Zachary beach park
All around lovely condo Close to all the action on downtown Key West
The apartment is beautifully decorated in a safe gated community within a few minutes walking distance to all of the attractions in Key West Sherri
Just a couple blocks from all the "action" yet quiet and peaceful for a good night's sleep
We enjoyed sitting on the patio with a glass of wine after a day in the sun
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5. Renovated home with a yard and pool (from USD 242)

This vacation house has more than a modern style. The light color shades used for the walls, bathroom, and ceiling and the large windows ensure a relaxing time. Their perfect backyard will allow your eyes to roam freely on the natural, colorful beautiful scenery. It is located one block away from the well-known Duval Street where you can shop and find restaurants to suit your taste. The spacious house ensures a relaxing experience. It’s also very close to beaches and is dog-friendly, which seals the deal.

Renovated home w/yard and porch. One block from Duval Street -dogs OK
3 reviews
House 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The house also has off-street gated parking for two vehicles
The house is spacious and very nicely furnished with large rooms/bathrooms and a phenomenal kitchen
They were friendly and helpful
Everyone went out of their way to make us feel welcome
I was so happy with this rental property that ten minutes after I entered the house
From the moment we arrived my family and I felt very comfortable dealing with the staff
The rental agents at Vacasa are wonderful to work with
Located one block from Duval
Also there is a white picket fence surrounding the entire property which gives you a feeling of privacy
The property was centrally located placing us within walking distance from almost every amenity in Key West
This house was absolutely beautiful and the location was perfect
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6. Shady and cozy house (from USD 139)

This house is cleverly designed. It has an American style kitchen, large windows with curtains to help you sleep better, lavish-styled bathroom, and a shady patio with decks and barbecue space. You should explore this area, not leaving any corner unvisited, including its sandy beaches and the famous Duval Street, which are just less than a minutes worth of walking.

centrally located up on Solaris Hill 2 blocks off Duval St.
Key West, FL, US
4 reviews
House 3 Bedrooms 2 Bathrooms
Top guest reviews
the owner is very accessible and helpful
he paid for our fishing charter and was very helpful with passing on his local knowledge
Read more reviews

7. Gorgeous home with a pool (from USD 325)

The unique feature of this house is the vibrant color combination of the clear blue pool, the bright green trees, the light shades of the house, and the red umbrella which makes the picture complete. Its well-furnished kitchen, large soft sofas, shiny wooden floors, and the seasonally heated pool are all features to leave you with an extraordinary experience.

~ INN COGNEATO COTTAGE ~ Gorgeous Home w/Pool in the <3 of Key West. Dogs OK
Key West, FL, US
9 reviews
House 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
It is short on closet space
Although still comfortable for four
We did NOT move the car as everything is nearby
The home is immaculate and freshly remodeled with upscale everything
Was a wonderful house and a wonderful stay
It was incredibly clean and
the house is extremely clean & comfortable walking distance to everything & the kitchen is awesome
I was very satisfied with the condition of the vacation rental
I was very satisfied with the condition of the vacation rental
I was very satisfied with the condition of the vacation rental
We would rent this home again in a heartbeat House keeping was great and the property manager was attentive and friendly
I was very happy with the location
I was very happy with the location
I was very happy with the location
I was very happy with the location
Faustos is a very easy walk
we found the Key West area in this condition
And the upper Duval restaurants and bars
The next door neighbors are long lineage Key West natives and know most every person that walks by and live in the neighborhood
We were also able to stay a few hours longer due to a late flight
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8. Get ready for a tan (from USD 579)

What is a better start to your day than having breakfast in a seaside cafe? This dog-friendly getaway can accept 6 guests as it has 2 bedrooms with 1 queen bed, 1 sofa bed, and 2 twin beds. It also offers a shared pool, WiFi, AC, washing/drying machine, and a canine companion for a little fee. This getaway is located a few minute’s walk from Higgs Beach Pier and dinning restaurants at Duval Street.

Dog-friendly getaway in a quiet, residential neighborhood w/ a shared pool
61 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
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9. Spacious modern luxurious villa

This splendid condo has 2 bedrooms and 2 bathrooms allowing its use by 4 guests. It is located in Shipyard which is a short walk away from Old Town. The master bedroom has a king bed and has its own private bathroom, while the second room has a queen bed and a view of the beautiful green scenery in the garden. You could bike ride to Fort Zachary Taylor Beach, Duval Street, and Mallony Square for shopping and restaurants. A private parking area is provided for guests. The glass doors between the living room and the patio allow fresh air to sweep the house and give you the perfect time to enjoy a morning coffee or a midnight glass of wine.

"VILLA AZUL" ~ Beautiful Unit Located in Truman Annex - Walk to all the Fun!
54 reviews
condo 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
Put small shelves on top of toilet for toiletries space and toilet paper holder
The beds were comfortable & the kitchen had everything we needed
The beds pillows and furniture were all very comfortable and there was ample seating for the four of us
We had 4 adults in a 2 bedroom condo & we had plenty of space
Guest bathroom needs to be updated
The unit was clean & more spacious than others
you can't beat the location
This unit was very clean and held more than we were expecting (right down to shampoo conditioner and body soap dispensers which after 8 nights were still half full ) -
Everything was as expected Clean property
Very clean and close to everything Brian
home away from home cozy feel Brian the property manager was very easy and pleasant to work with Very nice guy
We enjoyed the deck too
We would have given a five star rating BUT maintenance work required Very small items to complain about
He was very responsive and it helped making our stay very agreeable
I was very happy with the location
Perfect location to be near everything Plus Walking distance to Fort Zachary which is one of the best Snorkeling in the Keys
The location is perfect - within walking distance of major attractions but far enough away to be quiet & peaceful
We loved the location and could walk everywhere
and it was not a bad walk at all
This two bedroom apartment was in a great location in Key West Guest can easily walk or bicycle to all the fun
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10. A fabulous house that is close to the beach

Hosting 5 guests, it has 2 bedrooms with queen beds, a sofa bed, and 1 bathroom. This house is a lustrous unit with a private balcony and green unique garden. It is located in a great place where you can walk a few minutes to reach Duval Street, Mallory Square and the beach. Shops and supermarkets are also located a few blocks away. The guests are permitted to use the pool, WiFi, free parking and the fully equipped kitchen.

Truman Annex Shipyard with Tropical Garden
Key West, Florida, United States
32 reviews
Entire townhouse 2 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
great back patio and comfortable living area
pool area was a treat in the midday sun
the property was clean and comfortable
the space was clean
the condo was a clean comfortable end unit in a quiet neighborhood
his condo is great very clean and has everything you need
accommodations were comfy and clean would highly recommend this condo
craig is very responsive to any and all questions
the host craig was immediately available for any help and questions
great location close to duvall loop bus route
great location and cute space
great location walking distance to duval and the downtown waterfront
easy walk to duval street where many of the restaurants are located
perfect location our second year staying here
Read more reviews

A colorful trip

Renting a full-facility house that satisfies all your needs on a trip and exceeds your expectations will make you mentally and physically relaxed. Being close to attractions is a must, and who wouldn’t want to visit Key West for its green palm trees surrounded by the blue sea?

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

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