House & Vacation Rentals in Key West - HomeToGo base64Hash House & Vacation Rentals in Key West - HomeToGo

House & Vacation Rentals in Key West

Find 5,294 available offers from 14 partners
Key West
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Key West
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Popular Filters to find the Perfect Home Rental in Key West

2 Adults
4 Adults
Pool
2 Bedrooms
1 Bedroom
2 Bathrooms
6 Adults

This month's trending homes: most-clicked rentals

Discover offers in Key West that attract the most attention from other travelers

Cottage Key West
from $299
per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Key West with Grill, Pool & Yard, Close to West Martello Tower

Key West, Monroe County, Florida, United States
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House Key West
from $317
per night
House ∙ 4 guests ∙ 2 bedrooms

Charming House in Key West with Private Pool, Next to Southernmost Point

5.0
Outstanding (16 ratings)
Key West, Monroe County, Florida, United States
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House Key West
from $753
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Key West with Grill, Next to Southernmost Point

Key West, Monroe County, Florida, United States
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Vacation rentals and apartments with air conditioning

Condo  Key West
Jun 14 - Jun 21
-58%
$435
$182
per night
Condo ∙ 3 guests ∙ 1 bedroom

Condo in Key West with Free Parking, Close to Southernmost Point

4.6
Excellent (94 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
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House  Key West
Mar 1 - Mar 8
-19%
$402
$325
per night
House ∙ 9 guests ∙ 3 bedrooms

House in Key West, Close to Southernmost Point

4.7
Excellent
Key West, Monroe County, Florida, United States
Free cancellation
Air conditioning
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Condo  Key West
Apr 9 - Apr 16
$273
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Key West with Pool & Grill

4.6
Excellent (14 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
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Vacation rentals with Wi-Fi

Cottage  Key West
Sep 28 - Oct 5
$400
per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Cottage in Key West with Patio, Pool & Yard, Near Southernmost Point

4.8
Outstanding (48 ratings)
Key West, Monroe County, Florida, United States
Internet
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House  Key West
Oct 13 - Oct 20
-66%
$458
$155
per night
House ∙ 6 guests ∙ 2 bedrooms

Beautiful Vacation Home in Stock Island with Private Balcony, Next to Key West Tropical Forest & Botanical Garden + Garden Views

4.8
Outstanding (85 ratings)
Key West, Monroe County, Florida, United States
Internet
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Condo  Key West
Jul 6 - Jul 13
-51%
$423
$208
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Key West with Private Balcony + West-Facing Views

4.4
Very good (224 ratings)
Key West, Monroe County, Florida, United States
Internet
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Apartments and vacation rentals with a kitchen

Condo  Key West
May 17 - May 24
-62%
$514
$196
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Nice Condo in Key West with On-Site Parking

4.4
Very good (129 ratings)
Key West, Monroe County, Florida, United States
Kitchen
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House  Key West
Aug 9 - Aug 16
-52%
$634
$303
per night
House ∙ 4 guests ∙ 2 bedrooms

House in Key West with Pool, Grill & Yard, Near Mallory Square

4.9
Outstanding (37 ratings)
Key West, Monroe County, Florida, United States
Kitchen
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Condo  Key West
May 26 - Jun 2
$400
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Key West

5.0
Outstanding (10 ratings)
Key West, Monroe County, Florida, United States
Kitchen
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Best Vacation Home Deals in Key West

Save up to 63%

Condo Key West
May 17 - May 24
-25%
$1,000
$750
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Key West with Yard, Grill & Sauna, Next to West Martello Tower + Fabulous View + Beach Nearby

5.0
Outstanding (134 ratings)
Key West, Monroe County, Florida, United States
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Condo Key West
Aug 23 - Aug 30
-57%
$495
$212
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Wonderful Condo in Key West with On-Site Parking + West-Facing Views

4.4
Very good (224 ratings)
Key West, Monroe County, Florida, United States
View deal
Condo Key West
Sep 24 - Oct 1
-63%
$347
$128
per night
Condo ∙ 2 guests ∙ 1 bedroom

Beautiful Condo in Bahama Village with Pool, Next to Southernmost Point

4.4
Very good (278 ratings)
Key West, Monroe County, Florida, United States
View deal

Explore the 5,294 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 14 different providers.

Recommended Vacation Rentals in Key West

Find your perfect vacation rental in Key West: from $156 per night

Condo Key West
Aug 9 - Aug 16
-65%
$593
$211
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Charming Condo in Key West with On-Site Parking

4.4
Very good (129 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Jul 19 - Jul 26
-50%
$600
$300
per night
House ∙ 4 guests ∙ 2 bedrooms

House in Key West with Pool, Yard & Patio, Close to Mallory Square

4.9
Outstanding (55 ratings)
Key West, Monroe County, Florida, United States
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House Key West
Aug 9 - Aug 16
$1,029
per night
House ∙ 8 guests ∙ 4 bedrooms

Beautiful House in Key West with Private Pool, Close to Mallory Square + Fantastic View

4.6
Excellent (32 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Sep 21 - Sep 28
$285
per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful House in Stock Island with Botanical Garden, Close to Key West Tropical Forest & Botanical Garden

4.7
Excellent (187 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Sep 6 - Sep 13
-52%
$716
$340
per night
House ∙ 6 guests ∙ 2 bedrooms

House in Key West with Private Balcony + Direct View

4.6
Excellent (56 ratings)
Key West, Monroe County, Florida, United States
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House Key West
Jul 5 - Jul 12
-25%
$400
$300
per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Key West with Patio, Pool & Grill, Queen Sofabed, Close to Mallory Square

4.7
Excellent (62 ratings)
Key West, Monroe County, Florida, United States
View deal
Condo Key West
Sep 24 - Oct 1
-28%
$307
$221
per night
Condo ∙ 4 guests ∙ 1 bedroom

Lovely Condo in Key West with Pool & Patio, Close to Southernmost Point

4.4
Very good (76 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Aug 9 - Aug 16
$417
per night
House ∙ 8 guests ∙ 3 bedrooms

Lovely House in Stock Island with Pool, Patio & Grill

5.0
Outstanding (236 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Sep 6 - Sep 13
-70%
$456
$138
per night
House ∙ 6 guests ∙ 2 bedrooms

Charming House in Key West with Grill & Patio

4.5
Excellent (44 ratings)
Key West, Monroe County, Florida, United States
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Budget-friendly Vacation Rentals in Key West

Find Fantastic yet Inexpensive Offers

Condo Key West
Jun 14 - Jun 21
-48%
$288
$151
per night
Condo ∙ 3 guests ∙ 1 bedroom

Condo in Key West, Close to Southernmost Point

4.6
Excellent (94 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Sep 24 - Oct 1
-47%
$1,095
$575
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Key West with Patio, Yard & Pool, Next to Mallory Square

4.9
Outstanding (62 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Jul 5 - Jul 12
-23%
$493
$379
per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Key West with Pool & Patio, Near Mallory Square

4.5
Excellent (29 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

Cottage Key West
Sep 6 - Sep 13
-31%
$325
$225
per night
Cottage ∙ 3 guests ∙ 2 bedrooms

Cottage in Key West with Patio, Close to Mallory Square

5.0
Outstanding (158 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Sep 21 - Sep 28
-83%
$554
$97
per night
House ∙ 4 guests ∙ 1 bedroom

Vacation Home in Key West with Grill

4.9
Outstanding (32 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Oct 5 - Oct 12
$585
per night
House ∙ 6 guests ∙ 3 bedrooms

House in Key West with Private Pool, Next to Mallory Square

4.9
Outstanding (29 ratings)
Key West, Monroe County, Florida, United States
View deal

Popular Rental Amenities in Key West

  • Pool (4,264)
  • Pet-friendly (1,715)
  • Air conditioning (5,017)
  • WiFi (4,864)
  • Kitchen (3,435)
  • Parking (262)
  • Balcony/patio (2,787)
  • TV (4,794)
  • Washing machine (3,062)
  • Microwave (3,311)
  • Grill (1,585)
  • No smoking (4,920)

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 7 vacationers and have an average cost of $743 per night. If you would also like to be close to the water, many 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 August (8/2 – 8/9). Prices reach an average of $1,184 per night. In September (9/21 – 9/28), accommodation prices will be at their lowest at $447 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 August that you will find the week with the least available rentals (8/2 – 8/9). People tend to travel less to Key West during a week in September (9/28 – 10/5) when only 41% of the rentals are booked.

A Tropical Paradise at the Southernmost Point - Key West

Key West, the southernmost city in the continental United States, has always been a favored vacation spot for its unique blend of tropical charm, rich history and laid-back atmosphere. This small island city offers visitors a perfect escape with its year-round warm climate and stunning ocean views. Key West's vibrant culture is evident in its colorful Conch-style vacation rentals, diverse culinary scene and lively arts community. The island's compact size makes it easy to explore, whether on foot, by bike, or via the famous Conch Tour Train. Water enthusiasts can enjoy world-class snorkeling, diving and fishing in the surrounding crystal-clear waters. Key West's infamous sunset celebrations at Mallory Square, coupled with its eclectic nightlife along Duval Street, provide entertainment for all ages. With its perfect balance of relaxation and adventure, Key West offers a truly unique Florida Keys experience.

Top 6 Attractions and Where They Are

  1. Ernest Hemingway Home and Museum (907 Whitehead Street): The former residence of the famous author, now a museum showcasing his life and work.

  2. Southernmost Point Buoy (Corner of South and Whitehead Streets): A concrete buoy marking the southernmost point of the continental U.S.

  3. Mallory Square (400 Wall Street): A waterfront plaza famous for its daily sunset celebration featuring street performers and local artisans.

  4. Fort Zachary Taylor State Park (601 Howard England Way): A historic fort with beautiful beaches and snorkeling opportunities.

  5. Key West Butterfly and Nature Conservatory (1316 Duval Street): A tropical paradise filled with hundreds of butterflies and exotic birds.

  6. Duval Street: This bustling street is lined with bars, restaurants, shops and galleries, making it the heart of Key West’s nightlife and entertainment.

Best Time to Visit Key West

The best time to visit Key West is during the winter and early spring months, from December to April, when the weather is warm and dry, with temperatures ranging from the mid-60s to mid-80s Fahrenheit. This period is ideal for outdoor activities and enjoying the island’s natural beauty. However, it is also the peak tourist season, so the island can be crowded and accommodation prices are higher. For those looking to avoid the crowds, the shoulder seasons of late spring (May) and fall (September to November) offer warm weather and fewer visitors, though there is a higher chance of rain. Summer (June to August) is hot and humid, with frequent afternoon thunderstorms and the risk of hurricanes, making it less popular with tourists.

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 5,178 rentals
💳 Possible discounts up to 50%
🌙 Nightly prices starting at $156
⭐ Popular amenities Pool, Pets allowed and Air conditioning
🐾 Pet friendly homes 1,663 homes
🏊 Vacation rentals with pools 4,221 homes
10 reviews
Key West vacation rentals have an average rating of 4.2/5 on 10 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 $156 per night. Nightly prices for house rentals are $865 on average. Condos in Key West cost on average $639 per night.

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

There are 5,178 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 4,221 vacation rentals across 15 providers in Key West.

Are dogs allowed in vacation homes in Key West?

If you are traveling with a pet in Key West - 32% 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 $156.

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