Skip to main content

The best holiday homes in Key West

Check out our pick of great holiday homes in Key West

Filter by:


Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

All rooms feature a private bath, small refrigerator, and microwave. Apartments at Key West Villas include a fully-equipped kitchen and seating area.

Amazingly welcoming staff and incredible amenities. Such a fun atmosphere with their snacks, happy hour, pool, and great owners!

Show more Show less
9.7
Exceptional
352 reviews
Price from
US$280.12
per night

Popular points of interest near the holiday home include Ernest Hemingway Home and Museum, Duval Street and Southernmost Point. The nearest airport is Key West International Airport, 4 km from Just steps to Duval- Sleeps 10- Heated Pool House.

Location was awesome. Beds comfortable. Had everything we needed.

Show more Show less
9.8
Exceptional
5 reviews
Price from
US$965.50
per night

The spacious holiday home is equipped with 2 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with an oven, a microwave, a washing machine, a fridge and a stovetop. Towels and bed linen are provided in the holiday home. For added privacy, the accommodation features a private entrance.

Great location. Unit was a nice size.

Show more Show less
9.2
Superb
5 reviews
Price from
US$727.88
per night

The holiday home is equipped with 2 bedrooms, 2 bathrooms, bed linen, towels, a flat-screen TV with cable channels, a dining area, a fully equipped kitchen, and a balcony with sea views. For added privacy, the accommodation features a private entrance.

I loved everything about it.The place was so gorgeous and clean.The customer service was excellent.The master bedroom has a his and hers sink in the bathroom the shower was very big and nice.If I come back to Key West again I will choose to stay at this beautiful condo again.

Show more Show less
9.4
Superb
5 reviews
Price from
US$701.46
per night

The spacious holiday home features 3 bedrooms, a TV, a fully equipped kitchen with an oven and a microwave, and 4 bathrooms with an a bath or shower. Towels and bed linen are provided in the holiday home. For added privacy, the accommodation features a private entrance.

This is a perfect spot to stay in Key West. Great location - just a couple minutes walk to Duval Street. We rent entire unit and it was amazing. Apartments are clean, beautiful cuban style. we spend there only 2 night but it was amazing experience. Highly recommend it!

Show more Show less
9.8
Exceptional
6 reviews
Price from
US$1,495.95
per night

The spacious holiday home features 2 bedrooms, a flat-screen TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a bath. Towels and bed linen are featured in the holiday home. For added privacy, the accommodation features a private entrance.

Close to the ocean. Large rooms

Show more Show less
9.5
Exceptional
8 reviews
Price from
US$540.21
per night

Located in Key West, 1.4 km from Rest Beach and 1.6 km from Higgs Beach, 2x2 Fully Updated Old Town Waterfront Corner Condo offers a garden and air conditioning. Both free WiFi and parking on-site are available at the holiday home free of charge. The holiday home provides an outdoor swimming pool and a lift.

Such a beautiful room, so chill and quiet. But a beautiful experience.

Show more Show less
9.4
Superb
5 reviews
Price from
US$565.87
per night

The spacious holiday home features 2 bedrooms, a TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a bath. Guests can take in the ambience of the surroundings from an outdoor dining area.

Location was perfect pool looked amazing

Show more Show less
9.5
Exceptional
6 reviews
Price from
US$903.44
per night

Located in the centre of Key West, 600 metres from Fort Zachary Taylor State Park Beach and 1.2 km from Simonton Street Beach, Lavender Jungle by AvantStay Great Location w Patio Shared Pool Week Long Stays Only offers free WiFi and air conditioning. This holiday home provides accommodation with a patio. The property is non-smoking and is set 1.5 km from South Beach.

The holiday home features 2 bedrooms, a TV, a fully equipped kitchen with an oven and a fridge, a washing machine, and 1 bathroom with a bath.

Great location. Super helpful staff

Show more Show less
9.8
Exceptional
5 reviews
Price from
US$409.42
per night

The 2-bedroom holiday home has a living room with a TV, a fully equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a hair dryer.

Southernmost Point is 2.7 km from the holiday home, while Ernest Hemingway Home and Museum is 3.3 km from the property. The nearest airport is Key West International Airport, 2 km from Papaya Place by AvantStay Great Location w Balcony Outdoor Dining Shared Pool Hot Tub.

Slept 6. There is private and secure parking. This is a big deal in Key West. Full kitchen with everything you need for a family dinner.

Show more Show less
9
Superb
5 reviews

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.
Search holiday homes in Key West

Most booked holiday homes in Key West this month

Enjoy breakfast in Key West!

  • Key West Villas
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 352 reviews

    Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

    the personal touch the service was out of this world

  • Just steps to Duval- Sleeps 10- Heated Pool House
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 reviews

    Situated in Key West, 600 metres from South Beach and 1.6 km from Higgs Beach, Just steps to Duval- Sleeps 10- Heated Pool House offers a garden and air conditioning.

    Location was awesome. Beds comfortable. Had everything we needed.

  • New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 5 reviews

    Located in the centre of Key West, 600 metres from South Beach and 700 metres from Fort Zachary Taylor State Park Beach, New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool offers free WiFi...

  • Sunrise on the Atlantic
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 5 reviews

    Located in Key West, 400 metres from Smathers Beach and 600 metres from Rest Beach, Sunrise on the Atlantic offers free WiFi and air conditioning. This holiday home also features a pool with a view.

    The available amenities were very nice. The property is well maintained and inviting.

  • Julia Whitehead Guest Suites
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 6 reviews

    In the centre of Key West, located within a short distance of Fort Zachary Taylor State Park Beach and South Beach, Julia Whitehead Guest Suites offers free WiFi, air conditioning and household...

  • Leaward Isle Island Retreat
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 8 reviews

    Located in Key West, 400 metres from Smathers Beach and 600 metres from Rest Beach, Leaward Isle Island Retreat offers air conditioning.

  • 2x2 Fully Updated Old Town Waterfront Corner Condo
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 5 reviews

    Located in Key West, 1.4 km from Rest Beach and 1.6 km from Higgs Beach, 2x2 Fully Updated Old Town Waterfront Corner Condo offers a garden and air conditioning.

  • Amelia Home by AvantStay In Historic Old Town w Pool
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 6 reviews

    Located 500 metres from South Beach and 700 metres from Fort Zachary Taylor State Park Beach in the centre of Key West, Amelia Home by AvantStay In Historic Old Town w Pool provides accommodation with...

Save money on holiday homes in Key West – budget options available!

  • Lavender Jungle by AvantStay Great Location w Patio Shared Pool Week Long Stays Only
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 reviews

    Located in the centre of Key West, 600 metres from Fort Zachary Taylor State Park Beach and 1.2 km from Simonton Street Beach, Lavender Jungle by AvantStay Great Location w Patio Shared Pool Week Long...

  • Papaya Place by AvantStay Great Location w Balcony Outdoor Dining Shared Pool Hot Tub
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 5 reviews

    Set in Key West, 200 metres from Smathers Beach and 700 metres from Rest Beach, Papaya Place by AvantStay Great Location w Balcony Outdoor Dining Shared Pool Hot Tub offers air conditioning.

  • Baya House
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 7 reviews

    In a central area of Key West, located within a short distance of South Beach and Fort Zachary Taylor State Park Beach, Baya House offers free WiFi, air conditioning and household amenities such as a...

  • The Andros by Brightwild-4th Floor Sunset View
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 32 reviews

    Featuring air-conditioned accommodation with a patio, The Andros by Brightwild-4th Floor Sunset View is located in Key West.

    Très spacieux et très propre, très bon rapport qualité / prix

  • Sunrise Suites Cat Island Suite #205
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 6 reviews

    Set in Key West, 6.4 km from Southernmost Point and 7.3 km from Ernest Hemingway Home and Museum, Sunrise Suites Cat Island Suite #205 offers air-conditioned accommodation with a balcony and free WiFi...

    The location was good! It was nice to be out of the city

  • Key Lime Calypso
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 6 reviews

    Located 200 metres from Ernest Hemingway Home and Museum, Key Lime Calypso is a holiday home with a kitchen in Key West.

  • Bahama House
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 8 reviews

    Located in Key West, Bahama House is a holiday home with a private pool. This holiday home is 200 metres from Duval Street and 300 metres from Ernest Hemingway Home and Museum.

  • Crawl to Duval w/ Hot tub
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 7 reviews

    Featuring air-conditioned accommodation with a balcony, Crawl to Duval w/ Hot tub is located in Key West. This property offers access to a terrace and free private parking.

Great access to the city centre! Check these holiday homes in Key West

  • Keys Please by Brightwild
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 3 reviews

    Set in the centre of Key West, 300 metres from South Beach and 700 metres from Fort Zachary Taylor State Park Beach, Keys Please by Brightwild offers free WiFi, a garden and air conditioning.

  • Pilar Cottage by Brightwild
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Conveniently located in the centre of Key West, Pilar Cottage by Brightwild offers a patio, air conditioning, free WiFi and TV. With city views, this accommodation offers a swimming pool.

  • Smooth Sailing by Brightwild-Pool & Boat Dock
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Boasting air-conditioned accommodation with a private pool, sea view and a patio, Smooth Sailing by Brightwild-Pool & Boat Dock is situated in Key West.

  • Coastal Bliss by Brightwild-Pool, Parking, Dock!
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Featuring air-conditioned accommodation with a private pool, sea view and a patio, Coastal Bliss by Brightwild-Pool, Parking, Dock! is located in Key West.

  • Sophisticated Sunsets by Brightwild-Pool & Dock!
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Boasting air-conditioned accommodation with a private pool, sea view and a patio, Sophisticated Sunsets by Brightwild-Pool & Dock! is set in Key West.

  • Duval Sea Turtle by AvantStay Great Location Close to Shops Shared Pool
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Duval Sea Turtle by AvantStay Great Location Close to Shops Shared Pool is situated in the Downtown Key West district of Key West, 700 metres from Fort Zachary Taylor State Park Beach, 1.4 km from...

  • Two Duval Street Suites w parking and pool
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Situated in the centre of Key West, 700 metres from South Beach and less than 1 km from Fort Zachary Taylor State Park Beach, Two Duval Street Suites w parking and pool offers free WiFi and air...

  • Tropical Dreaming by AvantStay 4 BLKS to Beach Private Pool
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 3 reviews

    Located 500 metres from South Beach and 700 metres from Fort Zachary Taylor State Park Beach in the centre of Key West, Tropical Dreaming by AvantStay 4 BLKS to Beach Private Pool provides...

  • Contra House by Brightwild-Luxury Home With Pool
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Located in the centre of Key West, 1.1 km from South Beach and 1.2 km from Fort Zachary Taylor State Park Beach, Contra House by Brightwild-Luxury Home With Pool offers free WiFi, a garden and air...

  • Ibis by AvantStay Close to Duval Street w Shared Pool Month Long Stays Only
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Set in the centre of Key West, less than 1 km from South Beach and a 13-minute walk from Fort Zachary Taylor State Park Beach, Ibis by AvantStay Close to Duval Street w Shared Pool Month Long Stays...

  • Bahama Gardens - Turtle House
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    In the centre of Key West, located within a short distance of Fort Zachary Taylor State Park Beach and South Beach, Bahama Gardens - Turtle House offers free WiFi, air conditioning and household...

  • Bahama Gardens - Main House
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    In the centre of Key West, located within a short distance of Fort Zachary Taylor State Park Beach and South Beach, Bahama Gardens - Main House offers free WiFi, air conditioning and household...

  • Villa Positano by Brightwild-Rooftop Pool on Duval
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 3 reviews

    In a central area of Key West, located within a short distance of South Beach and Fort Zachary Taylor State Park Beach, Villa Positano by Brightwild-Rooftop Pool on Duval offers free WiFi, air...

  • Sky Loft in Key West by Brightwild
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 8 reviews

    In the centre of Key West, located within a short distance of Simonton Street Beach and South Beach, Sky Loft in Key West by Brightwild offers free WiFi, air conditioning and household amenities such...

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

  • Passover Cottage
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 3 reviews

    Passover Cottage is a holiday home in Key West, 600 metres from Ernest Hemingway Home and Museum, 800 metres from Duval Street, as well as 1 km from Southernmost Point.

  • Helen's Hideaway by Brightwild
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    Featuring air-conditioned accommodation with a private pool, city view and a patio, Helen's Hideaway by Brightwild is located in Key West.

  • NEW Grenada Suite - Parking Pool & Pets 209
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    Boasting air-conditioned accommodation with a patio, NEW Grenada Suite - Parking Pool & Pets 209 is situated in Key West.

  • Casita de Catherine by AvantStay 1 Block to Duval St w Hot Tub
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Casita de Catherine by AvantStay 1 Block to Duval St w Hot Tub is located in the Downtown Key West district of Key West, 500 metres from Fort Zachary Taylor State Park Beach, 1.3 km from Higgs Beach...

  • Rose Lane Villas
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 268 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 1.8 km from the Southernmost Point.

    clean. well equipped and the location was amazing.

  • Grand Marina Suite by Brightwild-Waterfront Condo
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 92 reviews

    Located in Key West, 9.1 km from Ernest Hemingway Home and Museum and 9.2 km from Duval Street, Grand Marina Suite by Brightwild-Waterfront Condo offers a garden and air conditioning.

    Me encantó la tranquilidad y lo lindo que estaba todo

  • The Exuma Cay by Brightwild-Pool View & Parking
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 14 reviews

    Boasting air-conditioned accommodation with a patio, The Exuma Cay by Brightwild-Pool View & Parking is situated in Key West.

  • Villa Coastal by Brightwild-Pool & Free Parking
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 13 reviews

    Right in the heart of Key West, situated within a short distance of South Beach and Fort Zachary Taylor State Park Beach, Villa Coastal by Brightwild-Pool & Free Parking offers free WiFi, air...

  • Duval Street Suite overlooking Duval with parking and pool
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2 reviews

    Situated in Key West, less than 1 km from Fort Zachary Taylor State Park Beach and 1.7 km from Simonton Street Beach, Duval Street Suite overlooking Duval with parking and pool offers air conditioning...

  • Bahama Gardens - Conch House
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 6 reviews

    In the centre of Key West, located within a short distance of Fort Zachary Taylor State Park Beach and South Beach, Bahama Gardens - Conch House offers free WiFi, air conditioning and household...

    The location was perfect, the staff friendly and helpful. Bikes available without costs

  • The Samana Cay by Brightwild-Private Balcony
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 23 reviews

    Boasting air-conditioned accommodation with a patio, The Samana Cay by Brightwild-Private Balcony is situated in Key West.

    - gute Ausstattung - große Wohnung - Pool und Whirlpool - genügend Handtücher

  • The St Martin by Brightwild-Hot Tub & Pool
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 6 reviews

    Located in Key West in the Florida region, The St Martin by Brightwild-Hot Tub & Pool has a patio. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • The Tortuga by Brightwild-Pool, Parking & Pets!
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 22 reviews

    Located in Key West in the Florida region, The Tortuga by Brightwild-Pool, Parking & Pets! has a patio. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

    Clean and had just what we needed for a short trip

  • Hemingway's View
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 20 reviews

    Located 60 metres from Ernest Hemingway Home and Museum and 400 metres Duval Street, Hemingway's View is a holiday home with a kitchen in Key West. This property is 600 metres from Southernmost Point.

    The house was great, clean, lot’s of room, the kitchen was great.

FAQ about holiday homes in Key West







Holiday homes that guests love in Key West

  • Avg. price/night: US$229.50
    7.1
    Scored 7.1
    Good
    Rated good
     · 1,505 reviews
    No breakfast Room very clean & modern
    Janeane
    Young couple
  • Avg. price/night: US$199.52
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2,571 reviews
    Very central location, quite and very clean.
    Hans-Peter
    Young couple
  • Avg. price/night: US$527.63
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 592 reviews
    The welcome at the Santa Maria Resort is very warm. Check-in done in just a few minutes. There is a nice parking and we had the suite/condo number 2. On the ground floor facing the swimming pool. The entire building faces the swimming pool. The two bedroom apartment is perfect. There is nothing to say. The furniture are a little bit old but it is very clean. Full kitchen. TVs everywhere. Laundry. Really perfect. The location is ideal 2 min. walk from DUVAL street with all the restaurants and shops.
    cedric
    Young couple
  • Avg. price/night: US$910.13
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 513 reviews
    It was calm and very peaceful. Roof top pool and bar was perfect. The private pools were just fabulous.
    Lynne
    Young couple
  • Avg. price/night: US$351.01
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 1,020 reviews
    Very clean, beautiful place and very well maintained. Pools were quiet and nice, as well the bar and the awesome bartender.
    Joao
    Young couple
  • Avg. price/night: US$199.52
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2,571 reviews
    Loved the location. Just at the end of Duval Street, very close to the beach and shops/restaurants. Hotel is typical in style of property in Key West. We had a huge suite at the front of the property with a lovely balcony. The kitchen/lounge area was very large. It was very clean. Lots of cupboard space. 2 double beds quite close together so be aware if not close friends with travelling companions! Swimming pool at back of property. We managed to park outside the hotel which was a bonus too.
    Liz
    Family with young children
  • Avg. price/night: US$279.52
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 1,065 reviews
    Excellent holiday home. I recommend it to everyone.
    Aleksei_LA
    Solo traveller
  • Avg. price/night: US$223.88
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 3,083 reviews
    Nice pool area, very clean, free parking, 10 minute walk to Duval
    SUE
    Young couple
  • 10
    Scored 10
    Exceptional
    Rated exceptional
     · 5 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: US$199.52
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2,571 reviews
    The location was great and only a short walk to all that Duval Street has to offer. There was tea and coffee available all day which was nice. The pool area and gardens are lovely and very clean. Our room was a great size.
    Susan
    Young couple

Research, refine and make plans for your whole trip