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

Vacation rentals with pools in Key West

Anytime
1 guest
Anytime
1 guest

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • Cabin
    • House

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • Air conditioning
    • WiFi
    • Kitchen
    • Parking
    • Balcony/patio
    • TV
    • Washing machine
    • Microwave
    • Dishwasher
    • Hot tub
    • Yard
    • Fireplace
    • Crib
    • Sauna
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Vacation rentals with pools in Key West: Recommended rentals

Vacation rentals with pools in Key West: find your perfect rental from just $154 per night!

Resort Key West
-70%
Dec 16 - Dec 23
Pool
Resort ∙ 127 guests ∙ 2 bedrooms

Resort with Terrace, Garden & Pool | Perfect for Remote Work | Pets Allowed

Key West, Monroe County, Florida, United States
$1,153$287
per night
Very good
$1,153$287
per night
View deal
Condo Key West
-49%
May 22 - May 29
Pool
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Pool, BBQ & Patio | Near Mallory Square

Key West, Monroe County, Florida, United States
$1,048$504
per night
Outstanding(107 ratings)
$1,048$504
per night
View deal
Cottage Key West
Nov 1 - Nov 8
Pool
Cottage ∙ 4 guests ∙ 1 bedroom

Nice Cottage with Pool, Terrace & BBQ | Near Southernmost Point | Nature View | Good for Workation

Key West, Monroe County, Florida, United States
$315
per night
Excellent(86 ratings)
$315
per night
View deal
House Key West
Jun 7 - Jun 14
Pool
House ∙ 6 guests ∙ 3 bedrooms

Family-Oriented House with Barbecue, Terrace & Pool | Close to Mallory Square | City View

Key West, Monroe County, Florida, United States
$363
per night
Outstanding(62 ratings)
$363
per night
View deal
House Key West
Jun 21 - Jun 28
Pool
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home with Patio, Grill & Pool | Near Key West Tropical Forest & Botanical Garden | Nature View | Perfect for Remote Work

Key West, Monroe County, Florida, United States
$380
per night
Outstanding(49 ratings)
$380
per night
View deal
Condo Key West
-58%
Nov 1 - Nov 8
Pool
Condo ∙ 2 guests ∙ 1 bedroom

Lovely Condo with Pool | Next to Southernmost Point | Next to the Beach

Key West, Monroe County, Florida, United States
$644$295
per night
Very good(277 ratings)
$644$295
per night
View deal
Villa Key West
Mar 29 - Apr 5
Pool
Villa ∙ 16 guests ∙ 7 bedrooms

Fully Equipped Villa with Patio, Private Pool & Barbeque | Next to Mallory Square | City View

Key West, Monroe County, Florida, United States
$1,993
per night
Outstanding(89 ratings)
$1,993
per night
View deal
House Key West
Jul 19 - Jul 26
Pool
House ∙ 8 guests ∙ 5 bedrooms

Vacation Home with Patio, Garden & Private Pool | Next to Mallory Square | Nature View

Key West, Monroe County, Florida, United States
$1,081
per night
Outstanding(63 ratings)
$1,081
per night
View deal
House Key West
-33%
Jun 4 - Jun 11
Pool
House ∙ 4 guests ∙ 3 bedrooms

Vacation Home with Yard, Patio & Pool | Close to Mallory Square | City View

Key West, Monroe County, Florida, United States
$742$407
per night
Outstanding(55 ratings)
$742$407
per night
View deal
House Key West
-55%
Jun 4 - Jun 11
Pool
House ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Spacious House with Terrace, Heated Pool & Barbeque | Next to Key West Tropical Forest & Botanical Garden | Nature View

Key West, Monroe County, Florida, United States
$996$304
per night
Outstanding(91 ratings)
$996$304
per night
View deal
Condo Key West
Jan 18 - Jan 25
Pool
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Heated Pool, Garden & Patio | Next to Southernmost Point | Nature View

Key West, Monroe County, Florida, United States
$298
per night
Excellent(46 ratings)
$298
per night
View deal
Cottage Key West
Nov 22 - Nov 29
Pool
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage with Patio, Yard & Heated Pool | Near Southernmost Point | City View

Key West, Monroe County, Florida, United States
$482
per night
Outstanding(48 ratings)
$482
per night
View deal
House Key West
Nov 22 - Nov 29
Pool
House ∙ 4 guests ∙ 2 bedrooms

Beautiful Vacation Home with Barbeque, Patio & Heated Pool | Near Mallory Square | City View

Key West, Monroe County, Florida, United States
$278
per night
Outstanding(134 ratings)
$278
per night
View deal
House Key West
-20%
Jun 21 - Jun 28
Pool
House ∙ 8 guests ∙ 3 bedrooms

Family-Oriented Nice Vacation Home with Garden, BBQ & Pool | City View | Good for Workation

Key West, Monroe County, Florida, United States
$592$318
per night
Outstanding(28 ratings)
$592$318
per night
View deal
House Key West
-33%
Jun 7 - Jun 14
Pool
House ∙ 6 guests ∙ 2 bedrooms

Family-Oriented Vacation Home with Pool | Near Mallory Square

Key West, Monroe County, Florida, United States
$1,075$480
per night
Outstanding(19 ratings)
$1,075$480
per night
View deal
Show all 7,188 properties

Top Deals: Discounts on vacation rentals with pools in Key West

Save up to 80%

House Key West
May 31 - Jun 7
-39%
$780
$496
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Terrace & Pool | Close to Mallory Square | City View

4.7
Excellent(64 ratings)
Key West, Monroe County, Florida, United States
Pool
View deal
House Key West
Aug 9 - Aug 16
-80%
$1,230
$440
per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home with Pool & Terrace | Next to Mallory Square | City View

4.7
Excellent(40 ratings)
Key West, Monroe County, Florida, United States
Pool
View deal
House Key West
Aug 30 - Sep 6
-79%
$993
$456
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Patio & Pool

4.6
Excellent(58 ratings)
Key West, Monroe County, Florida, United States
Pool
View deal

Information about Vacation rentals with pools in Key West

😎 Least busy month May
🥳 Busiest month January
🛏️ Popular home types Condo and House rental
🌡️ Hottest months August and July
❄️ Coldest months 65 °F in January and February
🌧️ Rainiest months September and August

Vacation rentals with pools in Key West: frequently asked questions

Vacation rentals with pools in Key West: What is the nightly price for a stay?

On average, you can get a great vacation rental for somewhere between $536 and $1,146 and find discounts up to 80%!

Vacation rentals with pools in Key West: can I find a vacation home suitable for a large group?

House rental in Key West usually fits 7 people.

Vacation rentals with pools in Key West: what kinds of vacation rentals can I book in Key West?

You can choose from 1,788 House rentals and 798 Condos in Key West right here on HomeToGo.

Discover other popular accommodation types

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