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The best vacation rentals in Key West

Check out our selection of great vacation rentals in Key West

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Southernmost Point Guest House & Garden Bar, hotel in Key West

This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 361 feet from the Southernmost Point and 240 feet from the beach.

We loved the gorgeous porch that we could sit and feel the breeze. The rooms were decorated beautiful and clean. Loved the location too, plus the coffee and breakfast every morning!
Scored 9.2
9.2
Rated wonderful
Wonderful
1,124 reviews
Price from
$113.85
per night
Key West Bed and Breakfast, hotel in Key West

Featuring garden views, Key West Bed and Breakfast in Key West features accommodations and a garden. The air-conditioned accommodations are a 19-minute walk from South Beach.

THE b&b WAS VERY NICE. HAD A WONDERFUL STAY ECEPT FOR THE HUMIDITY IN KEY WEST MADE THE TEMPERATUR FEEL LIKE 105 DEGREES. THE HOSTESS bELLA MADE THE HOTEL, SHE WAS VERY FREINDLY AND EGAR TO ASSIST. ELLA, ADVISED THE DO' AND DON'T OF WERE TO GO AND EAT, VISIT, ETC. EVEN THOUGH I PLANNED THE TRIP AND WHAT SIGHTS TO SEE WITHOUT BELLA AND HER GIDEANCE THE TRIP WOULD HAVE BEEN BASIC. WITH BELLA'S ASSISTANCE IT WAS WONDERFUL!!!!!!!!!!!!!!!
Scored 9.2
9.2
Rated wonderful
Wonderful
245 reviews
Price from
$189
per night
Andrews Inn & Garden Cottages, hotel in Key West

Located right off Duval Street, the Andrews Inn and Garden Cottages are less than 5 minutes’ walk from various dining and entertainment options. Guests can enjoy free WiFi and an outdoor pool.

Izabella at the reception was super helpful and friendly. The location and the room were perfect and the breakfast was delicious. We will definitely come back again.
Scored 9.4
9.4
Rated wonderful
Wonderful
122 reviews
Price from
$276.04
per night
Old Town Manor, hotel in Key West

This adult-only, pet friendly, smoke-free property is located in the heart of Key West less than 1 mi from the Southernmost Point.

Great welcome to the hotel. We stayed in the Saratoga suite which was lovely and had its own shaded patio area which was private, being surrounded by beautiful trees. The suite itself was well equipped and clean. There was plenty of coffee, sugar etc. & of course a coffee making machine. There was also a fridge and ice available from an ice machine nearby. The room was serviced daily and the bathroom was equipped with a nice range of complimentary shower gel, shampoo and conditioner. Breakfast was included which could be taken out on the large patio area or inside if preferred. There was plenty of variety in choice of breakfast. Staff were helpful and friendly. We parked in a nearby (discounted) public parking garage which was fine. We were able to use the pool in the sister hotel (villas) which was a couple of minutes walk away. The property is just off Duval Street which is a great location for restaurants, bars, shops and in walking distance of the main tourist attractions. We would definitely recommend Old Town Manor and would stay here again.
Scored 9.0
9.0
Rated wonderful
Wonderful
988 reviews
Price from
$305
per night
Key West Harbor Inn - Adults Only, hotel in Key West

Key West Harbor Inn - Adults Only in Key West provides adults-only accommodations with an indoor pool, an open-air bath, and a garden.

Clean nice property close to the strip. Staff is great very friendly and full of information. Rooms stayed cool and clean.
Scored 9.3
9.3
Rated wonderful
Wonderful
414 reviews
Price from
$200
per night
The Grand Guesthouse, hotel in Key West

This adults-only bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean.

Scored 9.1
9.1
Rated wonderful
Wonderful
695 reviews
Price from
$209
per night
Sky Loft in Key West by Brightwild, hotel in Key West

Sky Loft in Key West by Brightwild offers accommodations in Key West, a 9-minute walk from Ernest Hemingway Home and Museum and 0.7 miles from Mallory Square.

Great location. Very quiet and private but still close to Duval St. Blackout shades in bedroom made for excellent sleeping.
Scored 9.2
9.2
Rated wonderful
Wonderful
9 reviews
Price from
$225
per night
Key Lime Calypso, hotel in Key West

Key Lime Calypso is located in Key West, just 219 yards from Ernest Hemingway Home and Museum. Duval Street is 656 yards away. The accommodation is fitted with a TV with satellite channels.

Swimming pool Location Parking for Truck Washer and Dryer
Scored 9.2
9.2
Rated wonderful
Wonderful
5 reviews
Price from
$917
per night
Alexander's Gay Lesbian Guesthouse (Adult Only 21+), hotel in Key West

Set in a 3-story, conch-style home in Key West, Alexander's Gay Lesbian Guest house (Adult Only) offers air-conditioned guestrooms with free WiFi.

Lovely facilities, excellent breakfast, extremely well-run, delightful staff. A five-star inn!
Scored 9.7
9.7
Rated exceptional
Exceptional
36 reviews
Price from
$218.22
per night
Bahama House, hotel in Key West

Featuring air conditioning, Bahama House is located in Key West, just 219 yards from Duval Street. Ernest Hemingway Home and Museum is 328 yards away. All units have a TV and DVD player.

Location and private back yard with pool.
Scored 9.1
9.1
Rated wonderful
Wonderful
8 reviews
Price from
$866
per night
All vacation rentals in Key West

Most booked vacation rentals in Key West this month

Enjoy breakfast in Key West!

  • Old Town Manor
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 988 reviews

    This adult-only, pet friendly, smoke-free property is located in the heart of Key West less than 1 mi from the Southernmost Point.

    Climate place :) Great breakfast in the garden :)

  • The Grand Guesthouse
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 695 reviews

    This adults-only bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean.

    Great staff, super clean rooms, excellent location

  • Alexander's Gay Lesbian Guesthouse (Adult Only 21+)
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 36 reviews

    Set in a 3-story, conch-style home in Key West, Alexander's Gay Lesbian Guest house (Adult Only) offers air-conditioned guestrooms with free WiFi.

    Fantastic location with excellent tropical breakfast

  • The Conch House Heritage Inn
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 33 reviews

    This adult-only Conch House Heritage Inn offers accommodations in Key West with breakfast included and complimentary mimosas.

    Breakfast was wonderful - presentation was lovely.

  • Authors Key West Guesthouse
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 1,319 reviews

    Authors Key West Guesthouse features free Wifi and rooms with air conditioning in Key West.

    Really big room, nice and clean. A decent breakfast.

  • Courtney's Place Historic Cottages & Inns
    Scored 8.9
    8.9
    Rated excellent
    Excellent
     · 1,363 reviews

    Offering an outdoor pool, this historic Key West property is just 1 minutes’ walk from Duval Street. Free WiFi and a light continental breakfast are provided daily to all guests.

    Everything. We've stayed at Courtney's several times.

  • Caribbean House
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 529 reviews

    Featuring free WiFi throughout this adult-only property, Caribbean House offers accommodations in Key West.

    Clone to everything, very nice host,very clean,good breakfast

  • New Orleans House - Gay Male Adult Guesthouse
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 257 reviews

    Located above a nightclub on historic Duval Street in Key West, Florida, this gay male guest house features an outdoor swimming pool, a clothing-optional sundeck, and an on-site restaurant.

    Check-in was easy and everybody made us feel at home

These vacation rentals in Key West have options with FREE cancellation

  • New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 6 reviews

    New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool offers accommodations in Key West, a 7-minute walk from Duval Street and 0.4 miles from Southernmost Point.

  • Sky Loft in Key West by Brightwild
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 9 reviews

    Sky Loft in Key West by Brightwild offers accommodations in Key West, a 9-minute walk from Ernest Hemingway Home and Museum and 0.7 miles from Mallory Square.

    Great location. Very quiet and private but still close to Duval St. Blackout shades in bedroom made for excellent sleeping.

  • Alexander Palms Court - No Hidden Resort Fees!
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 909 reviews

    Alexander Palms Court - No Hidden Resort Fees! enjoys a location in Key West, a 6-minute walk from Southernmost Point and 0.7 miles from Ernest Hemingway Home and Museum.

    Great location, very nice, close to everything by foot

  • Grand Marina Suite by Brightwild-Waterfront Condo
    Scored 8.8
    8.8
    Rated excellent
    Excellent
     · 100 reviews

    Grand Marina Suite by Brightwild-Waterfront Condo offers accommodations in Key West, 5.7 miles from Ernest Hemingway Home and Museum and 5.7 miles from Duval Street.

    Me encantó la tranquilidad y lo lindo que estaba todo

  • Rose Lane Villas
    Free cancellation options available
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 279 reviews

    Located in Key West, Florida, these villas feature a heated outdoor swimming pool. They are adjacent to dining and shopping on Duval Street. and 1.1 mi from the Southernmost Point.

    clean. well equipped and the location was amazing.

  • The Casablanca Hotel
    Free cancellation options available
    Scored 8.8
    8.8
    Rated excellent
    Excellent
     · 543 reviews

    Less than 2 minutes’ walk from the Ernest Hemingway Home and Museum, this historic Key West property features guest rooms with private balconies and free Wi-Fi.

    The location is perfect! Staff is very friendly too

  • La Pensione Inn - Adult Exclusive
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 637 reviews

    Located in Key West, this ages 21 and older adult-only Florida bed and breakfast features an outdoor swimming pool and a daily continental breakfast.

    It is really nice and cozy and good neighbourhood.

  • Deluxe King with Balcony by Brightwild- at James House with Parking!
    Scored 8.1
    8.1
    Rated very good
    Very Good
     · 10 reviews

    Attractively located in Key West, Deluxe King with Balcony by Brightwild- at James House with Parking! has air-conditioned rooms, a garden and free WiFi.

    Beautiful room! Great location! Perfect Key West flavor!

Highly-rated vacation rentals in Key West

  • Westwinds Inn
    Scored 8.8
    8.8
    Rated excellent
    Excellent
     · 1,020 reviews

    Within walking distance of the beach, local attractions and activities, this Old Town Key West inn features on-site laundry facilities, comfortable guest rooms and an extended continental breakfast.

    Quiet but convenient for everything we wanted to do.

  • Seaport Inn
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 285 reviews

    Located in the heart of the historic Seaport District in Old Town, Seaport Inn features an outdoor pool and barbecue and is 1969 feet' walk from Mallory Dock.

    Nice location and good impression of Key West Living

  • Old Town Suites
    Scored 8.1
    8.1
    Rated very good
    Very Good
     · 426 reviews

    Located in Key West, Florida, these furnished self-catering apartments feature free WiFi access. The Ernest Hemingway Home and Museum is only 3 minutes’ walk away from Old Town Suites.

    Location, size of the apartment, separate bedrooms

  • Duval House
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 891 reviews

    Located centrally on lively Duval Street, Duval House offers a continental breakfast that includes Belgian waffles. The 7 Caribbean-style buildings offer free WiFi.

    the quirkyness of the cottage and beautiful gardens

  • Ambrosia Key West
    Scored 8.9
    8.9
    Rated excellent
    Excellent
     · 793 reviews

    This Key West bed and breakfast is 3 minutes’ walk from the art galleries and cafés of historic Duval Street. Guests can start their day with a full hot breakfast and enjoy two outdoor pools.

    The property looks really nice and location perfect

  • Road's End by Brightwild
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 8 reviews

    Road's End by Brightwild is located in Key West, just a 3-minute walk from Ernest Hemingway Home and Museum and half a mile from Southernmost Point.

    The location was great. Host were very helpful and nice.

  • Creme Brulee Suite by Brightwild
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 9 reviews

    Creme Brulee Suite by Brightwild offers accommodations in Key West, a 6-minute walk from Key West Aquarium and 500 yards from Mallory Dock.

    The location is PERFECT! Close to Duval and harbor area that we love. Second time we have stayed here, love it!

  • The Barbados by Brightwild-Bright Condo w Pool
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 60 reviews

    The Barbados by Brightwild-Bright Condo w Pool is located in Key West, just 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

    We had a chance to stay in Key West for reasonable price

FAQ about vacation rentals in Key West

Vacation Rentals That Guests Love in Key West

  • Avg. price/night: $617.63
    Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 654 reviews
    Had a 4 night stay here in Key West with the family, we booked a bi level 2 bedroom villa, it was really comfortable, it has everything you need. It is in an excellent location, if you're planning a trip to Key West, take a look here, Key West is a great place to visit.
    Ian
    Family with young children
  • Avg. price/night: $505.13
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 279 reviews
    best location!! plenty of space for the family!! i will surely come back and stay the villas!!
    Ailen
    Family with young children
  • Avg. price/night: $448.88
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 379 reviews
    Everything was wonderful. The villas had everything you needed to make your trip enjoyable. Looking forward to going back again soon.
    erica
    Group
  • Avg. price/night: $448.88
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 379 reviews
    Perfect location, but even more importantly, Heather and Kevin were dream hosts. The snacks, cocktails and customer service were outstanding. I would recommend Key West villas to everyone!
    Thomas
    Group
  • Avg. price/night: $227.50
    Scored 7.3
    7.3
    Rated good
    Good
     · 1,252 reviews
    This Marriott Fairfield Inn & Suites was pleasant. They provided a complimentary shuttle service to and from downtown Key West daily every hour. They also provided a complimentary shuttle to Smathers beach on the South. The pool at the center of the hotel 'village' was nice. It had fountains. The pool also had cabanas for families to hang out.
    James
    Family with young children
  • Avg. price/night: $505.13
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 279 reviews
    Absolutely beautiful great sized villa. Comfortable, convenient location, staff was excellent and villa was spotless. Parking and pet friendly with a nice pool - all excellent bonuses! So nice that when I walked in I immediately called the office and extended my stay by two nights!
    lisa
    Solo traveler
  • Avg. price/night: $342.61
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 2,722 reviews
    the villa was beautiful, we loved the privacy it provided.
    J
    John
    Family with young children
  • Avg. price/night: $345.11
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 1,033 reviews
    Excellent holiday home. I recommend it to everyone.
    Aleksei_LA
    Solo traveler
  • Scored 10
    10
    Rated exceptional
    Exceptional
     · 8 reviews
    This was an incredible holiday studio! It was very well equipped, very clean, spacious, beautifully decorated and in a fantastic part of town. The hosts were unbelievably helpful and responsive on messaging at all times. The bicycles they provided with the studio were so much appreciated for getting around Key West. The bed was super comfy and the studio is very quiet. Full kitchen provided if you wanted to cook. Top notch air con. Honestly never had a better holiday rental and cannot recommend it more highly! Would return in a heartbeat.
    Lucy
    Young couple
  • Avg. price/night: $277.88
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 2,806 reviews
    The pools were very nice. I absolutely loved the views from our Villa. The staff was very accommodating to all of our needs (we had 8 ladies, so we needed a lot of towels), ha ha.
    Aubrey
    Group

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