121 Properties in Truman Beach, Key West, Florida, United States of America. November 3, 2026 through November 17, 2026

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Key West

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Uptown - Upper Duval

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121 properties

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A dining area with round tables and wicker chairs, a ceiling fan, and a bar area in the background.

A poolside area with lounge chairs, a staircase leading to a balcony, and a pool.

The Southernmost Inn - Adults Only

Uptown - Upper Duval

2 outdoor pools

Hot tub on site

Breakfast incl

2 outdoor pools, Hot tub on site, Breakfast incl

Fully refundable

8.48.4 out of 10

Very Goodvery good

1,445 reviews(1,445 reviews)

$489 nightly

The current price is $8,339 total

$8,339 total

Total with taxes and fees

We have 1 left at this price

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An open door leading to a pool area with a wicker chair and a sofa inside a room with a view of the pool.

A poolside area with lounge chairs, umbrellas, and a pergola.

VIP Access

Ella's Cottages - Key West Historic Inns

Old Town Key West

Outdoor pool

Breakfast incl

Outdoor seats

Outdoor pool, Breakfast incl, Outdoor seats

Fully refundable

9.49.4 out of 10

Exceptionalexceptional

510 reviews(510 reviews)

$789 nightly

The current price is $13,140 total

$13,140 total

Total with taxes and fees

We have 1 left at this price

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A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.

A deck with sun loungers and a railing overlooking the sea.

VIP Access

Southernmost Beach Resort and Guesthouses

Uptown - Upper Duval

Beach bar

Spa

American restaurant

Beach bar, Spa, American restaurant

Fully refundable

8.68.6 out of 10

Excellentexcellent

3,615 reviews(3,615 reviews)

$4,545 off

$673 nightly

The current price is $11,628 total

$11,628 total

Total with taxes and fees

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Photo gallery for The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

Photo gallery for Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

Photo gallery for Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses