10 Resort-Feel HomeAway And Vrbo Vacation Rentals In Key West, Florida, USA

10 Resort-Feel HomeAway And Vrbo Vacation Rentals In Key West, Florida, USA
Eunice
Eunice  
Updated

The island city of Key West is part of the Florida Keys’ archipelago and it enjoys a tropical climate. For sun lovers seeking endless sunshine and long days frolicking with the fish at the Florida Reef, November through April are the best months to book a stay in Key West. Here’s a selection of gorgeous HomeAway and Vrbo vacation rentals in Key West that have all the makings of an exclusive coastal resort but are still close enough to everything:

1. Caribbean colours: "Tides on Simonton" (from USD 588)

This one bedroom cottage is just a block away from Duval Street, the main commercial street in Key West. From the outside,the cottage looks like a quaint doll house, emanating a peaceful aura with its soft shades of pastel blue and white paint. Step in through the doors and you’ll feel a wave of tranquility washing over you. The wood-vaulted high ceilings, hardwood floors, and glass windows illuminate the interior and create the perfect resort atmosphere. The walls are coated with the same lovely shade of light blue, bringing blue skies and clear waters right into the house. The bathroom is newly renovated and sparklingly clean. If two couples are staying here, one can sleep in the queen bedroom, while the sofa bed in the living room can accommodate the second couple. Both rooms have their own private entrance so your sleep will go undisturbed.

"TIDES ON SIMONTON" ~ Perfectly located just off Duval and all the fun!
101 reviews  Wifi Available
cottage 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
The only negative was it was difficult to find parking
The kitchen was well equipped if you wanted to cook
Overall apartment was clean- upon arrival there was garbage in the master bathroom with hair
The AC was nice and cold in the unit but the queen bed is probably ready to be replaced
As other commenters mentioned it is a bit noisy as the bedroom sits next to Simonton Suggestions for improvement would be the bed
Cleanliness:
The location was perfect and the rooms were clean and comfortable -
the house was comfortable and clean
The Tides on Simonton was exactly as described Charming comfortable Clean & close to everything
I was very satisfied with the condition of the vacation rental
I was very satisfied with the condition of the vacation rental
Host:
They were quick to reply and answer all questions
Loved the hardwood ceiling and floors
We knew we were going to be hit by hurricane Dorian
I was very happy with the location
I was very happy with the location
Location:
Overall stay was average Located close to everything but very loud
We had to park in the street several blocks away
Perfect house for a couple and walking distance to everything
see the botanic garden and to pick up a few groceries
Otherwise it was a very enjoyable stay and great location
Read more reviews

2. Duval action: Keylime Cottage (From 255 USD)

Key West FL HD Sloppy Joe's01
Source: Photo by user Ebyabe used under CC BY-SA 3.0

Just around the corner from popular Key West bars like Sloppy Joe’s and Irish Kevins, this 2nd-floor studio is perfect for 2. Decorated with warm tones of browns and golds, the studio is inviting and furnished with a king-sized bed and large flat-screen TV. The large shared deck overlooking the street below is perfect for lazy afternoons soaking in the rays while enjoying a refreshing glass of lemonade. If you have friends over, the shared courtyard will serve all your entertaining needs with the barbeque grill and plunge pool. A short walk transports you away from your quiet abode to where all the action happens: an area with bars, restaurants, and shops galore.

KEYLIME COTTAGE - 1 Block From All The Duval Action! Pvt Parking, Shared Pool

Area: Simonton Street

Price: From 255 USD

Number of Guests: 2

3. A Key escape: Gorgeous Home With Private Heated Pool (From 703 USD)

Lobster trap buoys on Angela Street- Key West, Florida (7486802920)
Source: Photo by user Florida Memory used under PUBLIC DOMAIN

This 3-storey home is a tropical paradise nestled in a convenient area close to Duval Street. A convenience store (CVS) is right across the street should you need to get anything. The dining room leads out to the sunny courtyard with a private heated pool and gas barbeque grill, great for an outdoor summer party. The common areas are cheerful and welcoming, the polished rose hardwood floors reflecting light all around. If your friends are partying hard below, head up the stairs to the privacy of the bedrooms. The master bedroom suite is a cosy space that occupies the entire 2nd floor. You have access to a large bathroom and 2 balconies overlooking the pool and gardens here. The 3rd floor houses the other 2 bedrooms. The sea is never far away, even in the bathroom. After the day’s activities, step into a soothing warm bath and feel yourself enter a state of peaceful relaxation.

A Key Escape - Gorgeous Home With Private Heated Pool - 1 Block To Duval

Area: Simonton Street / Angela Street

Price: From 703 USD

Number of Guests: 8

4. Seaport views: Ocean Breeze Loft Suites (from USD 1400)

This penthouse unit boasts splendid views overlooking the marina with the white yachts bobbing merrily on the water. The master bedroom downstairs has a huge bed and white shutters that open up to reveal the picture-perfect view. The living area is connected to the wide balcony where you can have a couple of ice cold beers with a gentle ocean breeze circulating around you. Marvel at the fiery hues of pink and orange reflected on the water’s surface when the sun sets. You won’t need to wait your turn to wash or brush your teeth. The master bedroom toilet comes with a double sink, perfect for couples. The shower area is also equipped with a hot tub jetted tub to pummel your aches away. For a different kind of view, head up to the rooftop deck where you can work on your golden tan in privacy.

Very Rare-The Galleon 3 King Bd, 3 Bath w/ 4th king bd in loft + sleeper sofa
Key West, FL, US
condo 3 Bedrooms 3 Bathrooms

5. Pilar's Secret: Old Town Home Hidden Off Duval (From 919 USD)

MM00032668
Source: Photo by user Florida Keys--Pub... used under CC BY 2.0

Named after novelist Ernest Hemingway’s famed fishing boat, “Pilar”, this luxurious vacation home is a true hidden gem. A back gate leads you to Duval Street in less than a minute, so you can see it all without having to stray too far away from this lush paradise. Whimsical string lighting across the pool area creates a dreamy atmosphere for a chilled out evening under the stars. If a midnight swim takes your fancy, jump right in; the pool can be heated. Modern yet homely with wooden ceilings and walls, the cosy living room is the ideal lounging space for those who seek the shade. It looks out to the lush pool area through white French doors so you can enjoy the pool view or watch some television on the comfy couch. This is what a true vacation is all about. There are two outdoor dining sets, one by the pool and one on the side patio right by the grill. Take your pick and have a cookout party! The outdoor shower is a thoughtful element that helps to keep the house clean. You can wash off the sand and salt water after a day out at the beach before you step inside the house. The 3 bedrooms are all simply delightful but the master suite, which occupies the whole second floor, is sure to be a hot favourite among everyone. This serene haven will make you look forward to bedtime. Take your time in the unique ensuite bathroom that looks like a spa. The others can wait! (Or, they can use the other equally lovely bathroom downstairs.)

:: PILAR'S SECRET @ OLD TOWN :: Hidden Off Duval / Private Pool / Renovated...

Address: Duval St / Lonely St

Price: From 919 USD

Number of Guests: 8

6. Newly renovated oceanfront condo (from USD 417)

Enjoy a few days in this charming newly renovated condo unit big enough for four people with superb amenities and a promising view of the ocean. There is a living room, kitchen cum dining area with stainless steel cookware for guests’ convenience. There is one comfy king bedroom with soft linens and plush pillows for a good night’s rest. The bathroom is clean and functional with shower essentials provided. Laundry facilities are also available in this condo, with a flat-screen smart TV, and even bicycles for guests to borrow while exploring the area. Nearby attraction to explore include Smathers Beach and South Beach for those who wish to just enjoy the sun, sand, and clear blue waters.

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
179 reviews  Wifi Available
condo 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the kitchen is gorgeous and the balcony is a lovely view
the room was better than the pictures and omg the sunrise was amazing i would defiantly stay here again
the new bathroom is outstanding
Cleanliness:
it is clean and very well decorated
the condo we strayed in was awesome so clean and it was so well decorated
Host:
she was very responsive and communicative when necessary
Location:
beautilfully appointed condo with a perfect location for us
so close to a fantastic beach
this unit is close to the water pool or beach and perfect biking distance from duval st
we would recommend this place to any of our parents and close friends
the new walk in tile shower is beautiful
Read more reviews

7. Bright open-plan apartment near Old Town (from USD 683)

A great option for families and friends traveling to Florida, this bright and airy two-bedroom condo is close to Old Town center. This open-plan condo has a comfy seating area, a fully-equipped kitchen, and a dining area where guests can use updated cookware to prepare their meals. The bedrooms are spacious with a king bed, queen bed, and single beds for guests to have a good night’s sleep on. The bathrooms are clean and have bathtubs and shower essentials provided for them to use during their stay. Outdoor amenities include a balcony overlooking the ocean, access to the swimming pool, and hot tub in the condo complex. Explore nearby attractions like Higgs Beach and Smathers Beach if you wish to experience some sand, sun, and fun while in sunny Florida.

Anchor Drop in Key West modern elegance, luxury finishes. Bike to Old Town
90 reviews
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 5
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
clean newly remodeled comfortable furniture nice amenities
excellent accommodations including pool and hot tub
pool and common areas are nice
Cleanliness:
our unit was clean and comfortable
super clean kitchen had everything tons of towels
the vacation rental was very clean
the vacation rental was very clean
the unit is spacious clean and well equipped
Host:
rating details:the property manager was adequately helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
Location:
i was 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
i was very happy with the location
Read more reviews

8. Quirky penthouse apartment in Key West (from USD 505)

Spend your summer days in Florida with a bang and book this quirky penthouse property for you and your family. It’s big enough for 5 people, with 2 bedrooms and 2 functional bathrooms they could make full use of. There is also a comfy living room area with a kitchen cum dining area where guests can eat meals and prepare them while enjoying some entertainment on the flat-screen TV. The penthouse has a balcony overlooking the Florida area and has other amenities like Wifi access, laundry facilities, cable TV, and parking space for those who drove up for a weekend or holiday. Spend a lazy afternoon by South Beach or explore Mallory Square for a good walk around the area if you want to keep active while on vacation.

Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
Key West, FL, US
35 reviews
condo 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
great pool area with superb views
the closet with pool toys/floats/chairs a nice touch for us
wonderful ocean views great pool and tennis courts
the pool was very nice with the view of the ocean from poolside
very comfortable great kitchen bathrooms and whirlpool were super also
Cleanliness:
however this one is clean comfortable and affordable
clean place is equipped with everything you need
the beds were very comfortable & everything was clean
extremely spacious condo huge bedrooms 3 sets of sliders to a huge patio
Host:
underground secure parking owner communicated with me quickly when we had questions
great accommodations very user friendly and accessible
Location:
this location had everything we needed and was in a great location
great beaches close by
very nice we are morning walkers so the location was perfect for a walk along the ocean
Read more reviews

9. Top floor oceanfront beachhouse (from USD 564)

Stay close to the beautiful beaches of Flordia, like Smathers Beach, South Beach, and Higgs Beach when you book this top floor oceanfront condo. It has everything you would need while on vacation, like a comfy living room, a dining area cum kitchen where guests can make full use of the appliances. There are two inviting bedrooms with window views of the deep blue ocean. Access to a clean dysfunctional bathroom is no issue since the property keeps it well maintained and offers guests free toiletries and shower essentials. This property is child-friendly and offers a parking space for those who drove up with a vehicle. Wifi access and cable TV are available in this property for some entertainment.

Top Floor Ocean Views from every window Newly Renovated for 2020
210 reviews  Wifi Available
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
nice view of ocean and pool from large balcony
the wall unit in the living room was our favorite
the pool and hot tub are amazing
our family loved the condo the pool was beautiful and the grounds of the property were gorgeous
Cleanliness:
condo was spacious and clean
clean up to date and safe
condo was very clean with everything you need for an enjoyable vacation
location was great condo clean and quiet
pool is amazing hot tub was always clean and working properly
Host:
a site map would be very helpful
Location:
just gorgeous comfy well maintained and the perfect location
the location view pool and property maintenance and security are great
Read more reviews

10. Spacious oceanview apartment (from USD 360)

Enjoy the best of what sunny Florida has to offer and stay a few nights in this charming and spacious apartment. Ideal for families or groups of friends, up to six people can make use of all the top-notch amenities. It has a living room with an outdoor balcony overlooking the ocean, as well as a fully decked out kitchen where guests can whip up a feast. The dining table can comfortably seat up to six people, while the bathroom is nice and clean with toiletries provided for guests’ convenience. There is a king bedroom and another bedroom with two single beds, and a sofabed in the living room for more guests to sleep on. Pets are not allowed in this property, but it is child-friendly with some toys and books available to keep the kids entertained during your stay.

Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
96 reviews  Wifi Available
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
a beautiful condo overlooking water and the pool
it is very spacious has a beautiful balcony overlooking the pool and ocean
this place has everything you could need on your vacation the furnishings are unique and so comfortable
b day super comfortable
Cleanliness:
the place was clean and equipped with everything
the condo was beautifully furnished and spotless
very clean condo with fantastic views
great condo location very clean easy process to check in and enjoy
we had everything we need and more very clean specious for our 6 member family
Host:
tom was super helpful and friendly and responded to questions quickly
the owner has thought of everything and has gone above and beyond for his guests’ comfort and enjoyment
Location:
the condo location was great
close enough to enjoy the duval crawl yet far enough away to truly relax
it is located right next to smathers beach which was perfect for morning walks
we truly enjoyed staying in this place
the property is beautiful incredibly quiet well situated and nicely appointed
Read more reviews

The key to your heart

Have you found the vacation home that unlocked your heart and got you booking a flight to Key West? I sure hope so!

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

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Eunice became hooked on travelling 2 years ago when she embarked on a student exchange programme in Stuttgart, Germany. Among the many places she’s visited, Europe has captured (most of) her heart...Read more

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