Vacation rentals in Key West - HomeToGo base64Hash Vacation rentals in Key West - HomeToGo

Vacation rentals in Key West

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Top 15 Recommended vacation rentals in Key West

Find your perfect vacation rental in Key West from just $135 per night!

Condo Key West
-81%
Sep 27 - Oct 4
Condo ∙ 6 guests ∙ 2 bedrooms

Family-friendly nice condo with hot tub & heated pool | Dogs allowed

Key West, Monroe County, Florida, United States
$912$172
per night
Very good(131 ratings)
$912$172
per night
View deal
Condo Key West
Sep 23 - Sep 30
Condo ∙ 8 guests ∙ 3 bedrooms

Fully equipped wonderful condo with barbecue, sauna & garden | Near Mallory Square

Key West, Monroe County, Florida, United States
$595
per night
Outstanding(99 ratings)
$595
per night
View deal
House Key West
-46%
Dec 7 - Dec 14
House ∙ 8 guests ∙ 4 bedrooms

House with grill, yard & heated pool | Next to West Martello Tower | City view | Perfect for remote work

Key West, Monroe County, Florida, United States
$859$464
per night
Outstanding(39 ratings)
$859$464
per night
View deal
Condo Key West
Aug 30 - Sep 6
Condo ∙ 8 guests ∙ 3 bedrooms

Family-friendly condo with sauna, yard & barbeque | Near West Martello Tower | Nature view | Next to the beach | Perfect for remote work

Key West, Monroe County, Florida, United States
$675
per night
Outstanding(136 ratings)
$675
per night
View deal
Accommodation Key West
-53%
Oct 4 - Oct 11
Accommodation ∙ 5 guests ∙ 1 bedroom

Beautiful rental with barbeque, yard & terrace | Near Southernmost Point

Key West, Monroe County, Florida, United States
$594$279
per night
Very good(914 ratings)
$594$279
per night
View deal
Houseboat Key West
May 31 - Jun 7
Houseboat ∙ 8 guests ∙ 4 bedrooms

Boat with barbeque & pool

Key West, Monroe County, Florida, United States
$135
per night
Excellent(7 ratings)
$135
per night
View deal
House Key West
-46%
Sep 27 - Oct 4
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped beautiful vacation home with grill, private pool & patio | Next to the beach | Pets allowed

Key West, Monroe County, Florida, United States
$754$410
per night
Outstanding(141 ratings)
$754$410
per night
View deal
Condo Key West
-79%
May 31 - Jun 7
Condo ∙ 6 guests ∙ 2 bedrooms

Family-oriented beautiful condo with pool | Near West Martello Tower | Beach nearby

Key West, Monroe County, Florida, United States
$1,540$323
per night
Very good(5 ratings)
$1,540$323
per night
View deal
Condo Key West
-86%
May 18 - May 25
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool & jacuzzi

Key West, Monroe County, Florida, United States
$2,148$307
per night
Excellent(5 ratings)
$2,148$307
per night
View deal
House Key West
Jan 27 - Feb 3
House ∙ 12 guests ∙ 6 bedrooms

Fully equipped house with heated pool, terrace & yard | Close to Southernmost Point | City view | Beach nearby

Key West, Monroe County, Florida, United States
$1,644
per night
$1,644
per night
View deal
Condo Key West
Sep 27 - Oct 4
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with heated pool, jacuzzi & terrace | Close to Southernmost Point

Key West, Monroe County, Florida, United States
$500
per night
$500
per night
View deal
Accommodation Key West
-26%
Jul 19 - Jul 26
Accommodation ∙ 2 guests ∙ 1 bedroom

Rental with yard, terrace & pool | Near Southernmost Point

Key West, Monroe County, Florida, United States
$303$225
per night
Very good(304 ratings)
$303$225
per night
View deal
House Key West
Sep 27 - Oct 4
House ∙ 12 guests ∙ 4 bedrooms

House with terrace & pool | Near Mallory Square | City view

Key West, Monroe County, Florida, United States
$681
per night
Excellent(28 ratings)
$681
per night
View deal
Condo Key West
-72%
Sep 23 - Sep 30
Condo ∙ 8 guests ∙ 4 bedrooms

Family-friendly big condo with sauna, hot tub & heated pool | Near West Martello Tower | Nature view | Close to the beach

Key West, Monroe County, Florida, United States
$1,731$487
per night
Excellent(168 ratings)
$1,731$487
per night
View deal
Condo Key West
-78%
Aug 22 - Aug 29
Condo ∙ 5 guests ∙ 2 bedrooms

Condo with hot tub, heated pool & sauna | Close to West Martello Tower

Key West, Monroe County, Florida, United States
$1,334$289
per night
Excellent(113 ratings)
$1,334$289
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Key West
Aug 30 - Sep 6
-21%
$910
$722
per night
Condo ∙ 8 guests ∙ 5 bedrooms

Condo with heated pool | Near Mallory Square | City view

4.9
Outstanding(40 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
View deal
House  Key West
Sep 27 - Oct 4
-78%
$1,172
$263
per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly vacation home with barbeque, heated pool & terrace | Nature view

4.9
Outstanding(152 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
View deal
Resort  Key West
May 25 - Jun 1
$215
per night
Resort ∙ 6 guests ∙ 2 bedrooms

Resort with pool, hot tub & terrace | Close to Mallory Square

4.7
Excellent(4 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
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Vacation houses with Balconies or Patios

House  Key West
May 16 - May 23
$436
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-friendly vacation home with terrace, garden & BBQ | Next to Mallory Square

4.7
Excellent(77 ratings)
Key West, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Key West
Sep 27 - Oct 4
-21%
$861
$682
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped house with private pool, patio & barbecue | Next to the beach

4.9
Outstanding(91 ratings)
Key West, Monroe County, Florida, United States
Balcony/Patio
View deal
Condo  Key West
Jun 6 - Jun 13
-55%
$989
$441
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped condo with heated pool | Next to West Martello Tower | Nature view | Beach nearby | Suitable for remote work

4.8
Outstanding(63 ratings)
Key West, Monroe County, Florida, United States
Balcony/Patio
View deal
See all offers

Vacation homes and rentals with a yard

House  Key West
Jul 12 - Jul 19
-31%
$1,310
$900
per night
House ∙ 10 guests ∙ 4 bedrooms

House with yard, terrace & private pool | Near Duval Street

4.5
Excellent(2 ratings)
Key West, Monroe County, Florida, United States
Yard
View deal
Houseboat  Key West
Jan 10 - Jan 17
$999
per night
Houseboat ∙ 11 guests ∙ 5 bedrooms

Boat with garden, patio & heated pool

5.0
Outstanding(98 ratings)
Key West, Monroe County, Florida, United States
Yard
View deal
House  Key West
Aug 30 - Sep 6
-68%
$1,666
$530
per night
House ∙ 6 guests ∙ 3 bedrooms

House with garden, private pool & patio | Close to Southernmost Point

4.8
Outstanding(107 ratings)
Key West, Monroe County, Florida, United States
Yard
View deal
See all offers

Best Vacation Home Deals in Key West

Save up to 77%

Condo Key West
Sep 4 - Sep 11
-74%
$815
$208
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-friendly wonderful condo with hot tub & pool | Pets are welcome

4.5
Excellent(5 ratings)
Key West, Monroe County, Florida, United States
View deal
Condo Key West
Sep 4 - Sep 11
-77%
$948
$216
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with jacuzzi & heated pool

4.2
Very good(134 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Aug 30 - Sep 6
-25%
$600
$450
per night
House ∙ 6 guests ∙ 3 bedrooms

House with pool | Close to Mallory Square | Nature view

4.9
Outstanding(78 ratings)
Key West, Monroe County, Florida, United States
View deal

Explore the 6,842 offers available in Key West and find a great place for a relaxing vacation. HomeToGo immediately shows the best offers by comparing all of the available vacation homes in Key West from 17 different providers.

Budget-friendly Vacation Rentals in Key West

Find Fantastic yet Inexpensive Offers

Condo Key West
May 19 - May 26
$450
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool & hot tub

5.0
Outstanding(76 ratings)
Key West, Monroe County, Florida, United States
View deal
Condo Key West
Sep 4 - Sep 11
-78%
$1,035
$225
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Children-friendly condo with hot tub & pool | Pets are welcome

4.3
Very good(115 ratings)
Key West, Monroe County, Florida, United States
View deal
Houseboat Key West
May 16 - May 23
$405
per night
Houseboat ∙ 6 guests ∙ 4 bedrooms

Boat with sauna & heated pool | Nature view

4.5
Excellent(121 ratings)
Key West, Monroe County, Florida, United States
View deal

Top-Rated Rentals and Accommodations in Key West

Book Vacation Rental Offers with the Highest User Rating

Condo Key West
May 28 - Jun 4
-73%
$1,386
$379
per night
Condo ∙ 5 guests ∙ 3 bedrooms

Fully equipped spacious condo with sauna, heated pool & hot tub | Close to West Martello Tower | Close to the beach

4.5
Excellent(113 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
May 5 - May 12
-64%
$1,649
$600
per night
House ∙ 6 guests ∙ 3 bedrooms

House with private pool, patio & barbecue | Near Mallory Square

4.6
Excellent(90 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
May 24 - May 31
-68%
$1,089
$348
per night
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly house with pool & terrace | Close to Mallory Square | City view

4.7
Excellent(46 ratings)
Key West, Monroe County, Florida, United States
View deal

Customer ratings and reviews

How are reviews collected?
Molly B.
Guest verified by HomeToGo

Check-in was a bit touchy, as the office was locked & unoccupied, despite the fact that the hours stated on the door said it should be open. Got that resolved. Condo unit was PERFECT! Beds were very comfortable! We loved the back deck & spent much time there! Staff was very friendly & accomodating!

Reviewed on 2/18/2024 | Group
Condo Key West
from $274
per night
HomeToGo
Condo ∙ 6 guests ∙ 1 bedroom
4.1
Very good(802 ratings)
Key West, Monroe County, Florida, United States
View deal
Cynthia F.
Guest verified by HomeToGo

Our 8 night stay at coconut Mallory was a 10/10. The room was just what we expected. Clean, very attractive landscaping, it was so nice to eat our self-prepared meals on our own little porch area. The kitchen was stocked with all of the cooking essentials we needed. A/c was cold The pools were perfect. Staff was awesome. We will definitely be coming back to this location.

Reviewed on 6/2/2023 | Couple
Condo Key West
from $212
per night
HomeToGo
Condo ∙ 2 guests ∙ 1 bedroom
4.1
Very good(801 ratings)
Key West, Monroe County, Florida, United States
View deal

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Popular Rental Amenities in Key West

  • Pool (5,013)
  • Pet-friendly (2,055)
  • Air conditioning (6,442)
  • WiFi (6,316)
  • Kitchen (4,987)
  • Parking (387)
  • Balcony/patio (2,896)
  • TV (5,936)
  • Washing machine (3,469)
  • Microwave (4,316)
  • Grill (1,912)
  • No smoking (6,082)

Many vacationers spend more time comparing vacation rentals offering pools. Two-thirds of the rentals offer access to a pool. Also, more hotel room include a pool than condo. Usually, hotel room with pools in Key West accommodate 8 vacationers and have an average cost of $742 per night. If you would also like to be close to the water, more than half of the vacation rentals with a pool are located within 2 miles of the waterfront.

Price and Availability Index in Key West

Click on any bar to see price and availability information

Vacation Rental Price Information in Key West

The above graph shows average prices of the vacation homes & apartments in Key West. The most expensive prices are in December (12/27 – 1/3). Prices reach an average of $742 per night. In September (9/20 – 9/27), accommodation prices will be at their lowest at $567 per night.

Rental availability information in Key West

Check out the graph above to find out how many rental homes are available in Key West throughout the year. It is in April that you will find the week with the least available rentals (4/4 – 4/11). People tend to travel less to Key West during a week in July (7/19 – 7/26) when only 44% of the rentals are booked.

What are the best activities for families in Key West?

8 Must-See Attractions in Key West

1. Key West Nature Preserve Park

If you're ready to leave your vacation home to enjoy some fresh air, head to this beautifuly preserved corner of town to enjoy a short hike through a lush mangrove forest.

2. Key West Marine Park

If your kids love swimming and snorkeling, look no further than this protected underwater park that stretches across 40 acres. Its two beaches are the perfect place for patient parents to relax while the kids enjoy the water.

3. Harry S. Truman Little White House

The winter White House for former president Harry S. Truman is a great place to learn about Key West's history. Local guides add color to the experience with their anecdotes.

4. Ernest Hemingway Home and Museum

Learn about the literary icon's numerous romantic relationships, friendships and writings through a guided tour of his erstwhile residence.

5. Dry Tortugas National Park

Seventy miles from Key West, this secluded park is home to Fort Jefferson, wild birds, coral reefs and marine life. It's the ideal location for a camping excursion.

6. Key West Butterfly and Nature Conservatory

Kids in particular will love this conservatory where nearly 60 species of butterflies thrive in a climate-controlled, glass-enclosed habitat.

7. Florida Keys Eco-Discovery Center

With such rich marine diversity in this part of Florida, it is only natural that Key West boasts a top-quality discovery center. Interactive displays about reefs and mangroves help visitors learn more and connect with nature.

8. Astro City

One of the most popular playgrounds in town located just across from Higgs Beach, Astro City is a great location for your kids to make new friends and precious memories.


What are the best places to discover the arts and culture of Key West?

Key West Culture

When it comes to culture and history, Key West has so much to offer. Explore the Audubon House and Tropical Gardens, a museum dedicated to the American painter, naturalist, and ornithologist John James Audubon.

Another must-visit for art enthusiasts is the Studios of the Key West, a community for artists which comprises work spaces, an exhibition hall, sculpture garden, and houses and cottages. An excellent program of performances, talks, and concerts is sure to cater to all tastes and interests.

In addition, be sure to check in advance if there are performances by the Key West Contemporary Dance Company, based at the Waterfront Playhouse. The Tennessee Williams Theater is another cultural hotspot, with a program packed with dance, theater, and musical performances.

Explore the former home of Nobel Prize-winning author Ernest Hemingway, where he lived and wrote during the 1930s. Visitors can tour the historic house, see Hemingway's personal belongings, and encounter the descendants of his famous polydactyl cats.

The Key West Art and Historical Society: This organization operates several cultural attractions in Key West, including the Custom House Museum, Fort East Martello Museum, and the Key West Lighthouse and Keeper's Quarters.

Learn about the fascinating world of maritime archaeology at the Mel Fisher Maritime Museum, which showcases artifacts recovered from shipwrecks in the waters surrounding Key West. Highlights include treasures from the Spanish galleon Nuestra Señora de Atocha.

Immerse yourself in the beauty of nature at the Key West Butterfly and Nature Conservatory, where visitors can stroll through lush gardens filled with thousands of butterflies from around the world.

A Tropical Paradise at the Southernmost Point - Key West

Best Neighborhoods for Vacation Rentals

Key West offers various areas suitable for vacation rentals, each with its own unique appeal:

  1. Old Town: The historic heart of Key West, close to major attractions like Mallory Square and Duval Street and nightlife .

  2. Truman Annex: A quiet, upscale neighborhood within Old Town near popular beaches and Duval Street.

  3. Bahama Village: A charming area known for its Caribbean influence and local flavor.

  4. New Town: A more residential area offering a quieter atmosphere and often lower prices.

  5. Stock Island: Located just east of Key West, offering a more laid-back, local experience.

  6. Casa Marina: Located near the southern coast of the island, this area offers beautiful beach access and luxurious rental options.

Popular Types of Vacation Rentals in Key West

Key West's vacation rental market caters to diverse preferences and group sizes:

  1. Condos and Apartments: Modern rentals that offer convenience and amenities such as pools and fitness centers, often found in New Town and along the waterfront or with ocean views.

  2. Cabins: Cozy options perfect for couples or small families.

  3. Waterfront homes: Properties with direct access to the water, providing stunning views, ideal for families or groups looking to enjoy Key West’s maritime activities.

  4. Bed and breakfasts: Intimate accommodations offering a more personalized experience.

  5. Luxury Villas: High-end accommodations with premium amenities such as private pools, spacious living areas and ocean views, ideal for those seeking a luxurious stay.

  6. Bungalows: Smaller, intimate properties perfect for couples or solo travelers looking for a unique and private retreat.

These varied rental options ensure that visitors can find accommodations that suit their needs, whether they're seeking a romantic getaway in a historic home, a family-friendly house with a pool, or a centrally located apartment for exploring all that Key West has to offer.

Information about vacation rentals in Key West

🏡 Vacation rentals available 6,842 rentals
💳 Possible discounts up to 78%
🌙 Nightly prices starting at $135
⭐ Popular amenities Pool, Pets allowed and Air conditioning
🐾 Pet friendly homes 2,039 homes
🏊 Vacation rentals with pools 5,000 homes
1,447,717 reviews
Key West vacation rentals have an average rating of 4.5/5 on 1,447,717 reviews left by travelers.

Frequently Asked Questions

What is the nightly price for a vacation rental in Key West?

The average accommodation in Key West is priced at $135 per night. Nightly prices for house rentals are $867 on average. Condos in Key West cost on average $622 per night.

How many vacation homes are available for booking in Key West?

There are 6,842 vacation rentals in Key West to browse and rent for your trip.

What are the most popular amenities for vacation rentals in Key West?

Three most popular amenities for vacation home rentals in Key West include accommodations that have: Pets allowed, Pool, and Air conditioning.

How many vacation homes with a pool are there in Key West?

There are 5,000 vacation rentals across 17 providers in Key West.

Are dogs allowed in vacation homes in Key West?

If you are traveling with a pet in Key West - 30% of rentals are pet-friendly.

What's the best month to travel to Key West?

Key West has its warmest time of year in August and July, with average nightly prices around $135.

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