Beachside Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Where to stay in Beachside

Find the best Beachside areas and neighborhoods for the activities you enjoy most. Learn more about Beachside
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Key West Historic District

4 out of top 10 points of interest in this area
4.5/5(66 area reviews)

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Ernest Hemingway Home and Museum.

Find hotels in Key West Historic District

Top hotels in Beachside

Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is S$459 per night from 17 Dec to 18 Dec
S$459
includes taxes & fees
17 Dec - 18 Dec
8.4/10 Very Good! (2,178 reviews)
"Everything"

Reviewed on 26 Nov,2024

Southernmost Beach Resort
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
The price is S$394 per night from 19 Dec to 20 Dec
S$394
includes taxes & fees
19 Dec - 20 Dec
8.6/10 Excellent! (1,786 reviews)
"Nice property. The room was great. Liked having a small kitchen. Bathroom had great space. Would stay again. Easy to navigate the property."

Reviewed on 25 Nov,2024

Margaritaville Beach House Key West
Havana Cabana at Key West - Adults Only
Havana Cabana at Key West - Adults Only
4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is S$283 per night from 4 Dec to 5 Dec
S$283
includes taxes & fees
4 Dec - 5 Dec
8.8/10 Excellent! (1,598 reviews)
"The property was just amazing. It’s clean and beautiful. Hot Tub / Swimming pool and the Bar side by with complimentary drinks it was really good !"

Reviewed on 24 Nov,2024

Havana Cabana at Key West - Adults Only
See all 2,928 properties in Beachside
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.

Popular places to visit

Smathers Beach showing a sandy beach, a luxury hotel or resort and tropical scenes

Smathers Beach

4/5(10 reviews)

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

Smathers Beach

Things to do

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

S$44
Per adult
80% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

S$44
Per adult
Full Day Trip in Key West from Miami
Island Adventure Eco Tour

Island Adventure Eco Tour – Explore the Hidden Backcountry with Kayaks

S$181
Per adult
98% of travellers recommend
Island Adventure Eco Tour – Explore the Hidden Backcountry with Kayaks
See all activities in Key West

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.