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The Latest Deals for Hotels with a pool in Key West

Discover well-known properties in Key West that are favored by visitors more than others. There are hotels in Key West and price data was last updated on August 22, 2025. The average price for a hotel in Key West is .
The following hotels are among the most sought after in the Key West area. Change the dates at the top of the page to see more options in Key West.

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The Garden House
The Garden House

The Garden House

329 Elizabeth Street, Key West, FL, United States
Bed & breakfast with an outdoor pool, a short walk to Duval Street An outdoor pool, self parking, and concierge services are available at this smoke-free bed & breakfast. Other amenities include express check-in, express check-out, and tour/ticket assistance. The Garden House offers 12 air-conditioned accommodations with hair dryers and complimentary toiletries. Flat-screen televisions come with cable channels. Bathrooms include showers. Housekeeping is provided daily. Recreational amenities at the bed & breakfast include an outdoor pool. The recreational activities listed below are available either on site or nearby; fees may apply.
Free Wi-Fi
Airport shuttle
8.7
Excellent
624 reviews
Location
0.3 mi from city centre
$153
View Deal
Colors On White
Colors On White

Colors On White

Key West, FL, United States
While you're here, you can enjoy all the comforts of home and more, including a stovetop and free WiFi, as well as a TV and air conditioning. Other amenities include towels, kitchenware and utensils, a picnic area, and rollaway beds.
Air Conditioning
7.4
Good
424 reviews
Location
0.6 mi from city centre
$152
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Hilton Garden Inn Key West/The Keys Collection
Hilton Garden Inn Key West/The Keys Collection

Hilton Garden Inn Key West/The Keys Collection

3850 North Roosevelt Boulevard, Key West, FL, United States
Daily Resort Charge includes: Shuttle service to Old Town Key West; two daily in-room bottled waters; beach amenities (chairs, umbrella & cooler); 20% off bicycle rentals for two; 10% off golf cart rentals; arts & crafts for kids. The best of Key West in easy reach We're off Highway 1, three miles from Duval Street and Smathers Beach, and walking distance from restaurants. The Ernest Hemingway House and Old Town can be reached in about 10 minutes, and Mallory Square is only four miles from our door. Enjoy our restaurant, outdoor pool bar, available downtown shuttle service, and 24-hour convenience shop.
Free Wi-Fi
7.2
Good
2897 reviews
Location
3.2 mi from city centre
$147
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Heron House Court - Adult Only
Heron House Court - Adult Only

Heron House Court - Adult Only

412 Frances Street, Key West, FL, United States
While you're here, you can enjoy all the comforts of home and more, including a refrigerator and free WiFi, as well as a garden and a rooftop terrace. Other amenities include designer toiletries, towels, tour/ticket assistance, and multilingual staff.
Free Wi-Fi
Air Conditioning
8.6
Excellent
70 reviews
Location
0.5 mi from city centre
$135
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The Casablanca Hotel
The Casablanca Hotel

The Casablanca Hotel

904 Duval Street, Key West, FL, United States
Less than 2 minutes’ walk from the Ernest Hemingway Home and Museum, this historic Key West property features guest rooms with private balconies and free Wi-Fi. A flat-screen TV with cable channels is provided in each spacious room at The Casablanca Hotel. A private bathroom is also provided in every air-conditioned guest room. Guests can enjoy a swim in the outdoor pool or relax on the sun deck at The Hotel Casablanca. Within walking distance of the beaches, shopping, dining and nightlife of Key West, this property is less than 10 minutes’ drive from Key West International Airport. South Beach and the Southernmost Point are within 1 mile of the hotel.
Free Wi-Fi
9.0
Excellent
1476 reviews
Location
0.2 mi from city centre
$152
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All hotels in Key West

HotelsCombined's insights for hotels with a pool in Key West

Use our HotelsCombined data-powered tips to help you find your next hotel with a pool in Key West.

How much does it usually cost to stay at a hotel with a pool in Key West?

On average, a hotel with a pool room in Key West costs about $303 per night. Rates can vary based on factors like seasonality, hotel star rating, and booking timing. The lowest price found on HotelsCombined in the last 7 days was $136.

What day of the week has the lowest rates for Key West hotels with a pool?

Hotels with a pool in Key West are most affordable on Thursdays, with average nightly rates around $272. Mondays are usually the most expensive, averaging $846 per night.

How much is a hotel with a pool in Key West tonight?

Users have found prices for hotels with a pool in Key West tonight starting as low as $218, rising to an average cost of $317, based on searches in the last 72 hours. Prices start from $230 for a 4-star hotel with a pool in Key West for tonight.

How much is a Key West hotel with a pool room this weekend?

In the past 72 hours, we’ve seen prices for hotels with a pool in Key West this weekend for as little as $231/night. If you’re specifically looking for a 3-star hotel this weekend, our users have found prices as low as $196/night. For a 4-star hotel with a pool in Key West, the cheapest rate recently found was $321/night for this weekend.

What’s the recommended booking timeframe for Key West hotels with a pool?

For the best rates, it's recommended to book your Key West hotel with a pool at least 58 days before your stay.
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Top-rated Hotels with a pool in Key West

Browse through properties in Key West that have received the highest ratings from guests. There are currently properties in Key West and data was last updated on August 22, 2025.
Our users rated these hotels as some of the best places to stay in Key West. Narrow down your search by reading user reviews, hotel descriptions, and amenities.
Authors Key West Guesthouse
Authors Key West Guesthouse

Authors Key West Guesthouse

725 White St. & Petronia, Key West, FL, United States
0.6 mi from city centre
Free Wi-Fi
$133
Avg. per night
View Deal
Blue Marlin Motel
Blue Marlin Motel

Blue Marlin Motel

1320 Simonton Street, Key West, FL, United States
0.6 mi from city centre
Free Wi-Fi
$141
Avg. per night
View Deal
Fairfield Inn & Suites by Marriott Key West at The Keys Collection
Fairfield Inn & Suites by Marriott Key West at The Keys Collection

Fairfield Inn & Suites by Marriott Key West at The Keys Collection

3852 North Roosevelt Boulevard, Key West, FL, United States
3.2 mi from city centre
Free Wi-Fi
$150
Avg. per night
View Deal
The Southernmost Inn-Adults Only
The Southernmost Inn-Adults Only

The Southernmost Inn-Adults Only

525 United Street, Key West, FL, United States
0.5 mi from city centre
Free Wi-Fi
Air Conditioning
$134
Avg. per night
View Deal
El Patio Motel
El Patio Motel

El Patio Motel

800 Washington Street, Key West, FL, United States
0.7 mi from city centre
Free Wi-Fi
Parking
$130
Avg. per night
View Deal

Other accommodations in Key West

Discover the ideal theme hotel, vacation rental or hostel for your stay in Key West. There are 2,475 properties in Key West and price data was last updated on August 22, 2025.
The Capitana Key West
The Capitana Key West

The Capitana Key West

2401 N. Roosevelt Blvd, Key West, Key West, FL, United States
1.5 mi from city centre
$264
Avg. per night
View Deal
Eden House
Eden House

Eden House

1015 Fleming Street, Key West, FL, United States
0.4 mi from city centre
Free Wi-Fi
$175
Avg. per night
View Deal
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront

3031-41 North Roosevelt Boulevard, Key West, FL, United States
2.1 mi from city centre
Free Wi-Fi
Parking
$171
Avg. per night
View Deal
Southwinds Motel
Southwinds Motel

Southwinds Motel

1321 Simonton Street, Key West, FL, United States
0.6 mi from city centre
$162
Avg. per night
View Deal
NYAH Key West - Adult Exclusive
NYAH Key West - Adult Exclusive

NYAH Key West - Adult Exclusive

420 Margaret Street, Key West, FL, United States
0.3 mi from city centre
Free Wi-Fi
Air Conditioning
$85
Avg. per night
View Deal
Duval House
Duval House

Duval House

815 Duval Street, Key West, FL, United States
0.2 mi from city centre
Free Wi-Fi
Air Conditioning
$144
Avg. per night
View Deal
Opal Key Resort & Marina
Opal Key Resort & Marina

Opal Key Resort & Marina

245 Front Street, Key West, FL, United States
0.4 mi from city centre
Free Wi-Fi
$310
Avg. per night
View Deal
Beachside Resort & Residences
Beachside Resort & Residences

Beachside Resort & Residences

3841 North Roosevelt Boulevard, Key West, FL, United States
3.2 mi from city centre
Free Wi-Fi
$183
Avg. per night
View Deal
DoubleTree by Hilton Grand Key Resort
DoubleTree by Hilton Grand Key Resort

DoubleTree by Hilton Grand Key Resort

3990 South Roosevelt Boulevard, Key West, FL, United States
3.2 mi from city centre
$179
Avg. per night
View Deal
The Cabana Inn Key West - Adult Exclusive
The Cabana Inn Key West - Adult Exclusive

The Cabana Inn Key West - Adult Exclusive

413 Applerouth Lane, Key West, FL, United States
0.1 mi from city centre
Free Wi-Fi
Air Conditioning
$176
Avg. per night
View Deal

Find better results for your stay in Key West

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