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

Vacation rentals in Key West

Browse 5,695 available vacation homes and compared across 14 trusted partners
Anytime
Guests
Anytime
Guests

Top 15 most Recommended Vacation Rentals in Key West

Discover your ideal Key West vacation rental with real-time comparisons of 5,678 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Key West
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped big house with heated pool & terrace | Close to Key West Tropical Forest & Botanical Garden | Nature view

Key West, Monroe County, Florida, United States
from $359
per night
Very good(148 ratings)
from $359
per night
View deal
Condo Key West
Condo ∙ 4 guests ∙ 1 bedroom

Condo with pool & barbeque | Close to Mallory Square | City view | Good for workation

Key West, Monroe County, Florida, United States
from $256
per night
Very good(2 ratings)
from $256
per night
View deal
House Key West
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, jacuzzi & private pool | Close to Key West Tropical Forest & Botanical Garden

Key West, Monroe County, Florida, United States
from $222
per night
Outstanding(4 ratings)
from $222
per night
View deal
House Key West
House ∙ 2 guests ∙ 2 bedrooms

House with pool | Near Southernmost Point | Nature view

Key West, Monroe County, Florida, United States
from $227
per night
from $227
per night
View deal
House Key West
House ∙ 10 guests ∙ 4 bedrooms

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

Key West, Monroe County, Florida, United States
from $1,052
per night
Excellent(7 ratings)
from $1,052
per night
View deal
Accommodation Key West
Accommodation ∙ 4 guests ∙ 1 bedroom

Beautiful rental with yard, pool & terrace | Next to Southernmost Point

Key West, Monroe County, Florida, United States
from $349
per night
Very good(307 ratings)
from $349
per night
View deal
House Key West
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with grill & patio

Key West, Monroe County, Florida, United States
from $188
per night
from $188
per night
View deal
House Key West
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped wonderful vacation home with terrace, barbecue & garden | Next to West Martello Tower | Nature view

Key West, Monroe County, Florida, United States
from $315
per night
Outstanding(14 ratings)
from $315
per night
View deal
House Key West
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with patio, barbecue & yard | Next to West Martello Tower | Nature view

Key West, Monroe County, Florida, United States
from $237
per night
Very good(16 ratings)
from $237
per night
View deal
Cabin Key West
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with heated pool, grill & terrace | Close to Southernmost Point | Nature view

Key West, Monroe County, Florida, United States
from $125
per night
Excellent(2 ratings)
from $125
per night
View deal
Condo Key West
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with grill, heated pool & jacuzzi

Key West, Monroe County, Florida, United States
from $231
per night
Outstanding(124 ratings)
from $231
per night
View deal
House Key West
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with heated pool, grill & patio | Next to Duval Street | City view

Key West, Monroe County, Florida, United States
from $420
per night
from $420
per night
View deal
Condo Key West
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped condo with patio, grill & pool | Next to Key West Tropical Forest & Botanical Garden

Key West, Monroe County, Florida, United States
from $508
per night
Outstanding(2 ratings)
from $508
per night
View deal
House Key West
House ∙ 6 guests ∙ 3 bedrooms

Spacious house with private pool | Close to Duval Street | Nature view

Key West, Monroe County, Florida, United States
from $246
per night
Outstanding(4 ratings)
from $246
per night
View deal
House Key West
House ∙ 14 guests ∙ 5 bedrooms

Fully equipped spacious house with garden, private pool & BBQ | Nature view | Good for workation | Pets are welcome

Key West, Monroe County, Florida, United States
from $418
per night
Outstanding(14 ratings)
from $418
per night
View deal

Vacation houses with Balconies or Patios

Cabin  Key West
from $193
per night
Cabin ∙ 2 guests ∙ 1 bedroom

Cottage with pool, BBQ & patio | Close to Duval Street | Nature view

4.7
Excellent(8 ratings)
Key West, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Key West
from $189
per night
House ∙ 4 guests ∙ 2 bedrooms

House with heated pool, garden & patio | Near Key West Tropical Forest & Botanical Garden | Nature view

5.0
Outstanding(6 ratings)
Key West, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Key West
from $169
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with private pool & patio | Close to Key West Tropical Forest & Botanical Garden

4.4
Very good(6 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
from $2,523
per night
House ∙ 21 guests ∙ 8 bedrooms

House with private pool, garden & patio | Near West Martello Tower | City view

Key West, Monroe County, Florida, United States
Yard
View deal
House  Key West
from $564
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with BBQ, garden & terrace

Key West, Monroe County, Florida, United States
Yard
View deal
House  Key West
from $962
per night
House ∙ 10 guests ∙ 5 bedrooms

Fully equipped house with grill, terrace & private pool | Close to West Martello Tower | Close to the beach

4.6
Excellent(10 ratings)
Key West, Monroe County, Florida, United States
Yard
View deal
See all offers

Vacation rentals and apartments with air conditioning

House  Key West
from $193
per night
House ∙ 4 guests ∙ 2 bedrooms

Family-oriented charming vacation home with barbeque & private pool | Close to Key West Tropical Forest & Botanical Garden | Pet-friendly

Key West, Monroe County, Florida, United States
Air conditioning
View deal
House  Key West
from $515
per night
House ∙ 8 guests ∙ 4 bedrooms

House with grill & private pool | Close to Duval Street | City view

5.0
Outstanding(8 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
View deal
House  Key West
from $262
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with barbecue, terrace & private pool | City view | Good for workation

5.0
Outstanding(12 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Key West offering exceptional value for money

Condo Key West
from $337
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Children-friendly condo with hot tub, sauna & garden | Nature view | Close to the beach

4.6
Excellent(163 ratings)
Key West, Monroe County, Florida, United States
View deal
Condo Key West
from $699
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Fully equipped condo with heated pool | Close to West Martello Tower | Nature view | Next to the beach | Good for workation

4.9
Outstanding(65 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
from $588
per night
House ∙ 8 guests ∙ 3 bedrooms

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

4.8
Outstanding(45 ratings)
Key West, Monroe County, Florida, United States
View deal

Top-Rated Vacation rentals in Key West

Book the highest-rated Key West vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Accommodation Key West
from $279
per night
Accommodation ∙ 4 guests ∙ 1 bedroom

Rental with patio, pool & garden | Close to Southernmost Point

4.6
Excellent(16 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
from $434
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly vacation home with yard, private pool & grill | City view | Pets allowed

5.0
Outstanding(8 ratings)
Key West, Monroe County, Florida, United States
View deal
Condo Key West
from $230
per night
Condo ∙ 5 guests ∙ 2 bedrooms

Condo with hot tub, heated pool & grill | Next to West Martello Tower

4.5
Excellent(4 ratings)
Key West, Monroe County, Florida, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Key West

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 $269
per night
Condo ∙ 6 guests ∙ 1 bedroom
4.1
Very good(803 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 $207
per night
Condo ∙ 2 guests ∙ 1 bedroom
4.1
Very good(802 ratings)
Key West, Monroe County, Florida, United States
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Key West

  • Pool (4,616)
  • Pet-friendly (1,830)
  • Air conditioning (5,384)
  • WiFi (5,234)
  • Kitchen (3,817)
  • Parking (385)
  • Balcony/patio (2,903)
  • TV (5,144)
  • Washing machine (3,337)
  • Microwave (3,515)
  • Grill (1,949)
  • No smoking (5,123)

Many vacationers spend more time comparing vacation rentals offering pools. Most 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 4 vacationers and have an average cost of $760 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 March (3/14 – 3/21). Prices reach an average of $692 per night. In September (9/19 – 9/26), accommodation prices will be at their lowest at $584 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 November that you will find the week with the least available rentals (11/7 – 11/14). People tend to travel less to Key West during a week in December (12/20 – 12/27) when only 40% 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 5,678 rentals
💳 Possible discounts up to 11%
🌙 Nightly prices starting at $128
⭐ Popular amenities Pool, Pets allowed and Air conditioning
🐾 Pet friendly homes 1,829 homes
🏊 Vacation rentals with pools 4,593 homes
590 reviews
Key West vacation rentals have an average rating of 3.5/5 on 590 reviews left by travelers.

Frequently Asked Questions

What is the price per night for a vacation home in Key West?

The price of a night's stay in Key West starts at $128. Nightly prices for house rentals are $964 on average. Condos in Key West cost $655 per night on average.

How many vacation homes are available to book in Key West?

Currently there are 5,678 rentals from 14 different providers in Key West.

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

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

How many vacation homes with pools are in Key West?

Key West has 4,593 Hotel room and Condo on offer to book.

Are pets allowed in vacation homes in Key West?

In case if you are traveling with a pet in Key West - 32% of rentals are pet-friendly.

Top cities to visit

Find more vacation rental types in Key West

Similar vacation rentals nearby

Most Popular Destinations

Show more
image-tag