Hotels with Pool in Old Town, FL

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  2. Hotels with Pool
  3.  USA
  4.  Florida
  5.  Key West
  6.  Old Town
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Explore 243 Hotels with Pool in Old Town from $181

Truman Hotel
Truman Hotel
Hotel
Key West, FL, USA
0.1k from Old Town center

Accommodations, Pools, Parking, Romantic, Boutique, 3-star, Lodgings, Places to stay, Family

8.9

Fabulous

3248 reviews

$244
Average price / night
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Paradise Inn Key West - Adults Only
Paradise Inn Key West - Adults Only
Hotel
819 Simonton Street, Key West, FL, 33040, United States
0.2k from Old Town center

AC, Breakfast Included, Free Parking, Hot Tub, Microwave, Outdoor Space, Parking Available, Pool, TV

9.2

Superb

1006 reviews

$290
Average price / night
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Paradise Inn - Adult Exclusive
Paradise Inn - Adult Exclusive
Hotel
Key West, FL, USA
0.2k from Old Town center

B&bs, Accommodations, Pools, Parking, Inns, Romantic, 3-star, Lodgings, Hot tubs

8.4

Very Good

715 reviews

$270
Average price / night
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Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns
Hotel
725 Truman Avenue, Key West, FL, 33040, United States
0.2k from Old Town center

AC, Bar, Breakfast Included, Crib, Free Parking, Heater, Housekeeping, Internet, Microwave

9.2

Superb

1237 reviews

$431
Average price / night
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Almond Tree Inn - Adults Only
Almond Tree Inn - Adults Only
Hotel
Old Town, Key West, Florida, USA
0.2k from Old Town center

Accommodations, Pools, Parking, Romantic, Boutique, 3-star, Lodgings, Hot tubs, Places to stay

9.4

Superb

278 reviews

$889
Average price / night
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Almond Tree Inn Hotel - Adults Only
Almond Tree Inn Hotel - Adults Only
Hotel
512 Truman Ave, Key West, FL, 33040, United States
0.2k from Old Town center

AC, Bar, Breakfast Included, Frontdesk 24 Hour, Hot Tub, Housekeeping, Internet, Laundry, Microwave

10.0

Exceptional

1005 reviews

$437
Average price / night
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H2O Suites - Adults Only
H2O Suites - Adults Only
Hotel
1212 Simonton Street, Key West, FL, 33040, United States
0.3k from Old Town center

AC, Bar, Elevator, Fitness Equipment, Frontdesk 24 Hour, Housekeeping, Internet, Laundry, Living Area

9.8

Exceptional

594 reviews

$630
Average price / night
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The Mermaid & The Alligator
The Mermaid & The Alligator
Hotel
Key West, FL, USA
0.2k from Old Town center

Accommodations, Pools, Lodgings, Hot tubs, Places to stay

9.3

Superb

148 reviews

$2197
Average price / night
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Orchid Key Inn - Adults Only
Orchid Key Inn - Adults Only
Hotel
1004 Duval St, Key West, FL, 33040, United States
0.3k from Old Town center

AC, Bar, Breakfast Included, Frontdesk 24 Hour, Hot Tub, Housekeeping, Laundry, Microwave, Outdoor Space

9.8

Exceptional

1002 reviews

$451
Average price / night
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Ella's Cottages - Key West Historic Inns
Ella's Cottages - Key West Historic Inns
Hotel
Key West, FL, USA
0.3k from Old Town center

Accommodations, Pools, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.5

Very Good

187 reviews

$399
Average price / night
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La Te Da - Adult Only, 21 or older
La Te Da - Adult Only, 21 or older
Hotel
Old Town, Key West, Florida, USA
0.3k from Old Town center

Accommodations, Pools, 3-star, Lodgings, Places to stay, Accessible hotels

9.0

Fabulous

156 reviews

$285
Average price / night
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Silver Palms Inn
Silver Palms Inn
Hotel
830 Truman Ave, Key West, FL, 33040, United States
0.3k from Old Town center

AC, Breakfast Included, Elevator, Frontdesk 24 Hour, Housekeeping, Internet, Microwave, No Smoking, Pool

9.4

Superb

1020 reviews

$335
Average price / night
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Room w/ Queen Bed in Vibrant Key West! Enjoy Romantic Ambience near Attractions
Room w/ Queen Bed in Vibrant Key West! Enjoy Romantic Ambience near Attractions
Hotel
Key West, FL, 33040, United States
0.4k from Old Town center

AC, Breakfast Included, Dryer, Free Parking, Heater, Internet, Laundry, No Smoking, Pool

10.0

Exceptional

2 reviews

$472
Average price / night
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Southernmost Inn Adult Exclusive
Southernmost Inn Adult Exclusive
Hotel
Key West, FL, USA
0.3k from Old Town center

B&bs, Accommodations, Pools, Inns, Romantic, 3-star, Lodgings, Hot tubs, Places to stay

7.8

Good

1411 reviews

$546
Average price / night
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Wicker Guesthouse
Wicker Guesthouse
Hotel
Key West, FL, USA
0.3k from Old Town center

B&bs, Accommodations, Pools, Parking, Inns, Romantic, Pet-friendly, 3-star, Lodgings

8.0

Good

2911 reviews

$242
Average price / night
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Douglas House
Douglas House
Hotel
Key West, FL, USA
0.3k from Old Town center

B&bs, Accommodations, Pools, Parking, Inns, Romantic, Pet-friendly, 3-star, Lodgings

9.0

Fabulous

2665 reviews

$260
Average price / night
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La Pensione Inn - Adult Exclusive
La Pensione Inn - Adult Exclusive
Hotel
Old Town, Key West, Florida, USA
0.3k from Old Town center

Accommodations, Pools, Parking, Romantic, 3-star, Lodgings, Vacation rentals, Places to stay, Accessible hotels

8.7

Fabulous

644 reviews

$511
Average price / night
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The Gardens Hotel
The Gardens Hotel
Hotel
Old Town, Key West, Florida, USA
0.4k from Old Town center

Accommodations, Pools, Parking, Romantic, 4-star, Lodgings, Places to stay, Accessible hotels

9.7

Exceptional

141 reviews

$1074
Average price / night
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Blue Marlin Motel
Blue Marlin Motel
Hotel
Key West, FL, USA
0.4k from Old Town center

Accommodations, Pools, Motels, Parking, Lodgings, Places to stay, Family, Accessible hotels

8.8

Fabulous

4720 reviews

$181
Average price / night
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Lighthouse Hotel - Key West Historic Inns
Lighthouse Hotel - Key West Historic Inns
Hotel
Key West, FL, USA
0.4k from Old Town center

Accommodations, Pools, Romantic, Pet-friendly, 3-star, Lodgings, Places to stay, Family, Accessible hotels

8.7

Fabulous

604 reviews

$310
Average price / night
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Papa's Hideaway
Papa's Hideaway
Hotel
Key West, FL, USA
0.5k from Old Town center

Accommodations, Pools, 3-star, Lodgings, Vacation rentals, Places to stay, Family, Self-catering, Beach rentals

9.2

Superb

30 reviews

$2451
Average price / night
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Pro Tip for Travelers:
HotelsWithSuites simplifies your search by aggregating premium inventory from global leaders like Booking.com, Expedia, and Vrbo. Whether you need oceanfront hotels, a private pool, or a pet-friendly suite, use our Advanced Filters to instantly compare the top-rated Hotels with Pool in Old Town.

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HotelsWithSuites can help you find hotels, resorts, and suites near many of 's top attractions, neighborhoods, and points of interest.

Old Town Hotels with Pool on the Map

Frequently Asked Questions

Hotels with pools in Old Town may offer indoor, outdoor, rooftop, or heated pools. Some properties also feature family-friendly or infinity pool options.

You can find 243 hotels with pools in Old Town, with prices starting from around $181 per night, making them accessible for various budgets.

Availability depends on the property and climate. Indoor or heated pools are often open year-round, while outdoor pools may be seasonal.

Yes, many properties also provide features like Pool, Guest Services, and Balcony/Terrace alongside pool access.

Yes, you can refine your search based on pool type, guest ratings, amenities, and pricing to find the best match for your stay.