Find hotels with pools in Truman Annex, Key West from $111

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Top Truman Annex Hotels with a Pool

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Weatherstation Inn

Weatherstation Inn

2.5 star property
Old Town Key West
  • Outdoor pool
  • Pool loungers
  • Near the beach
9.4 out of 10, Exceptional, (986)
$191 nightly
The price is $215
Nov 20 - Nov 21
Total with taxes and fees
Weatherstation Inn
Outdoor pool
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
  • Outdoor pool
8.4 out of 10, Very Good, (317)
$259 nightly
The price is $291
Dec 8 - Dec 9
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West
A heated pool
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Old Town Key West
  • Near the beach
9.4 out of 10, Exceptional, (47)
$967 nightly
The price is $1,072
Nov 24 - Nov 25
Total with taxes and fees
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 star property
New Town
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Hot tub
8.0 out of 10, Very Good, (1126)
Swimmers splash into vacation mode at the outdoor pool oasis, complete with stylish cabanas, comfortable loungers, and a refreshing poolside bar. Beyond the water, this Key West hotel offers bicycle rentals, fitness facilities, and convenient shuttle service.
$112 nightly
The price is $126
Dec 2 - Dec 3
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4.0 star property
Stock Island
  • 2 outdoor pools
  • 2 poolside bars
  • Pool loungers
9.4 out of 10, Exceptional, (1152)
Immerse in 2 outdoor pools with elegant loungers and refreshing drinks from poolside bars. Beyond the aquatic sanctuary, guests enjoy bicycling, boating excursions, and dining at waterfront restaurants with breathtaking sunset views.
$186 nightly
The price is $210
Nov 25 - Nov 26
Total with taxes and fees
The Perry Hotel & Marina Key West
Outdoor pool
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 star property
Summerland Key
  • Outdoor pool
8.2 out of 10, Very Good, (1002)
Splash into serenity at the heated outdoor pool overlooking beautiful ocean vistas. This hotel balances aquatic bliss with active pursuits, offering tennis courts, marina access, kayaking, and boat tours, all amid peaceful surroundings praised by guests.
$99 nightly
The price is $111
Nov 23 - Nov 24
Total with taxes and fees
Sugar Loaf Lodge
2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4.0 star property
New Town
  • 2 outdoor pools
  • 2 poolside bars
  • Pool loungers
  • Hot tub
8.0 out of 10, Very Good, (1704)
Cooling waters beckon at 2 outdoor pools complete with private cabanas, sun loungers, and poolside bars serving refreshing drinks. Active guests enjoy mini golf, bicycling, and a 24-hour fitness center between dips.
$157 nightly
The price is $177
Dec 1 - Dec 2
Total with taxes and fees
Blue Flamingo Resort Key West
Building design
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3.0 star property
Old Town Key West
  • 2 outdoor pools
  • Pool loungers
  • Near the beach
  • Hot tub
8.2 out of 10, Very Good, (1189)
Poolside serenity awaits at this Victorian adults-only haven with 2 sparkling outdoor pools and a soothing hot tub. Complimentary breakfast, bike rentals, and proximity to Duval Street create a perfect balance of relaxation and exploration.
$169 nightly
The price is $190
Nov 23 - Nov 24
Total with taxes and fees
The Southernmost Inn - Adults Only
4 outdoor pools, pool umbrellas, sun loungers
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4.0 star property
Northside Resort
  • 4 outdoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (1158)
Aquatic luxury defines this island escape where 4 pristine pools invite endless relaxation. Comfortable loungers, pool umbrellas, and a vibrant poolside bar create perfect days, while nearby water adventures from kayaking to sailing await the adventurous.
$186 nightly
The price is $209
Nov 30 - Dec 1
Total with taxes and fees
Parrot Key Hotel & Villas
Outdoor spa tub
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3.0 star property
Key West Historic District
  • 3 outdoor pools
  • Pool loungers
  • Near the beach
  • Hot tub
7.8 out of 10, Good, (1005)
Refreshing waters beckon across multiple pool areas with sun loungers for perfect relaxation. Beyond swimming, guests enjoy complimentary continental breakfast, bicycle rentals for island exploration, and a rooftop terrace offering an elevated retreat experience.
$120 nightly
The price is $136
Nov 20 - Nov 21
Total with taxes and fees
NYAH Key West - Adults Only
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Truman Annex Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"It was great! The room was amazing! Jodi at the front desk is awesome!"
Melanie 3-night trip
Posted 21 hours ago
Southernmost Beach Resort and Guesthouses

Frequently asked questions

What's it like visiting Truman Annex?
If spending time by the pool is your idea of a great getaway, you might want to think about Truman Annex, which offers 16 places to stay with pools. While you're here, you can explore attractions like Duval Street, and then unwind poolside at one of the accommodations in Truman Annex that travelers like for their pools.
What are some accommodations with pools in Truman Annex?
Hyatt Vacation Club at Sunset Harbor, Key West: Apartment, 4-minute walk from Duval Street. Features complimentary wireless internet access, an outdoor pool, and televisions. Weatherstation Inn: B&B, 5-minute walk from Duval Street. Offers continental, an outdoor pool, and free self parking. Beachside Resort & Residences: Hotel located near Smathers Beach. Provides a private beach, an outdoor pool, and 2 restaurants. Blue Flamingo Resort Key West: Hotel located near Smathers Beach. Features 2 restaurants, 2 outdoor pools, and 2 pool bars. Oceans Edge Key West Resort, Hotel & Marina: Hotel located near Smathers Beach. Offers complimentary bicycles, 6 outdoor pools, and complimentary wireless internet access.
How many hotels with pools can I expect to find in Truman Annex?
Expedia's 16 hotels in Truman Annex give you a great choice for your poolside getaway.
What is there to see and do in Truman Annex?
Explore places like Duval Street while you're in the area. Make a point to visit attractions like Mel Fisher Maritime Museum and USCGC Ingham Maritime Museum.

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