Find hotels with pools in Key West Historic District, Key West from $139

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Top Key West Historic District Hotels with a Pool

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, (1000)
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.
$123 nightly
The price is $139
Nov 12 - Nov 13
Total with taxes and fees
NYAH Key West - Adults Only
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, (1174)
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.
$146 nightly
The price is $165
Nov 11 - Nov 12
Total with taxes and fees
The Southernmost Inn - Adults Only
3 outdoor pools, pool umbrellas, sun loungers
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4.0 star property
Old Town Key West
  • 3 outdoor pools
  • 2 poolside bars
  • Pool loungers
  • On the beach
  • Full-service spa
8.6 out of 10, Excellent, (2863)
Sparkling waters beckon across 3 outdoor pools where sun loungers and umbrellas create perfect relaxation zones. Sip refreshing cocktails from 2 poolside bars while gazing at ocean panoramas, then rejuvenate with beachfront yoga or indulgent spa treatments.
$242 nightly
The price is $272
Nov 30 - Dec 1
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
Outdoor pool
The Garden House

The Garden House

3.0 star property
Key West Historic District
  • Outdoor pool
  • Near the beach
9.2 out of 10, Wonderful, (664)
$139 nightly
The price is $153
Nov 12 - Nov 13
Total with taxes and fees
The Garden House
Exterior
Heron House - Adult Only

Heron House - Adult Only

3.5 star property
Old Town Key West
  • Outdoor pool
  • Near the beach
9.0 out of 10, Wonderful, (1136)
Surrounded by verdant foliage, the outdoor pool offers a tranquil retreat after exploring nearby Duval Street attractions. Guests appreciate the immaculate pool area with comfortable sun decks, shaded seating, and the rooftop terrace views.
$178 nightly
The price is $200
Nov 16 - Nov 17
Total with taxes and fees
Heron House - Adult Only
3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4.0 star property
Old Town Key West
  • 3 outdoor pools
  • Poolside bar
  • Pool loungers
  • Near the beach
9.2 out of 10, Wonderful, (1033)
$244 nightly
The price is $274
Nov 30 - Dec 1
Total with taxes and fees
Winslow's Bungalows - Key West Historic Inns
Courtyard
Duval House

Duval House

3.0 star property
Old Town Key West
  • Pool loungers
  • Near the beach
9.4 out of 10, Exceptional, (1043)
Glide into the heated pool surrounded by lush gardens at this tranquil Key West retreat. Complimentary breakfast delights guests daily, while bicycle rentals provide perfect island exploration opportunities, all steps from Duval Street attractions.
$177 nightly
The price is $196
Nov 12 - Nov 13
Total with taxes and fees
Duval House
View from room
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4.0 star property
Old Town Key West
  • Outdoor pool
  • Poolside bar
  • Near the beach
  • Hot tub
9.2 out of 10, Wonderful, (1001)
$289 nightly
The price is $325
Dec 1 - Dec 2
Total with taxes and fees
Opal Key Resort & Marina, Key West
Outdoor pool, pool umbrellas, sun loungers
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 star property
Old Town Key West
  • Outdoor pool
  • Pool loungers
  • Near the beach
  • Hot tub
9.2 out of 10, Wonderful, (1001)
Surrounded by lush tropical gardens, the serene outdoor pool area invites guests to unwind on comfortable loungers under shade umbrellas. Bicycle rentals make exploring Key West effortless after rejuvenating in the clean hot tub.
$192 nightly
The price is $216
Nov 24 - Nov 25
Total with taxes and fees
Paradise Inn Key West - Adults Only
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers
Heron House Court - Adult Only

Heron House Court - Adult Only

3.0 star property
Key West Historic District
  • Outdoor pool
  • Pool loungers
  • Near the beach
9.0 out of 10, Wonderful, (1019)
Refreshing waters await in the outdoor pool, open from morning until evening in this tranquil adult-only retreat. Guests praise the exceptionally helpful staff, quiet atmosphere, and rooftop terrace views at this centrally located guesthouse.
$143 nightly
The price is $161
Nov 10 - Nov 11
Total with taxes and fees
Heron House Court - Adult 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 Key West Historic District Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Wonderful place to stay. Uber pickup was easy. Trolly available across the street for trolly. We had great dining options."
Teresa Weatherford 4-night trip
Posted 2 days ago
Southernmost Beach Resort and Guesthouses

Frequently asked questions

What's it like visiting Key West Historic District?
If lounging next to a pool is your idea of the perfect getaway, you may want to consider Key West Historic District, which offers 138 places to stay with pools. While you're visiting, you can explore attractions like Duval Street, and then relax poolside at one of the accommodations in Key West Historic District that travelers like for their pools.
What are some accommodations with pools in Key West Historic District?
Southernmost Beach Resort and Guesthouses: Hotel steps from South Beach. Features 2 pool bars, 3 outdoor pools, and a full-service spa. The Reach Key West, Curio Collection by Hilton: Resort steps from South Beach. Offers a private beach, an outdoor pool, and a full-service spa. Hyatt Centric Key West Resort and Spa: Resort, 3-minute walk from Duval Street. Provides a full-service spa, a pool, and a snack bar/deli. La Concha Key West, Autograph Collection: Hotel, 1-minute walk from Duval Street. Features 3 restaurants, an outdoor pool, and 2 bars. Opal Key Resort & Marina, Key West: Hotel steps from Mallory Square. Offers 3 bars, an outdoor pool, and spa services.
How many hotels with pools will I find in Key West Historic District?
Expedia's 138 hotels in Key West Historic District give you a great choice for your poolside getaway.
What is there to see and do in Key West Historic District?
Explore places like Duval Street while you're in Key West Historic District. The picturesque setting of Audubon House and Tropical Gardens and Key West Butterfly and Nature Conservatory showcase the area's natural beauty. Key West Historic District appeals to visitors with its bar scene and great live music scene.

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