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Check availability on Key West Luxury Hotels

Top Luxury Hotels in Key West

6 outdoor pools, free pool cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
Stock Island
  • 24-hour gym
  • Poolside bar
  • Concierge services
9.0 out of 10, Wonderful, (1740)
Waterfront opulence defines this marina-side retreat where 6 outdoor pools invite leisurely days under the Florida sun. Premium bedding, furnished balconies, and attentive concierge service create an atmosphere of refined coastal luxury at every turn.
The price is S$318
includes taxes & fees
30 Nov - 1 Dec
Oceans Edge Key West Resort, Hotel & Marina
3 outdoor pools, pool umbrellas, pool loungers
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4.0 star property
Key West Historic District
  • Near the beach
  • Poolside dining
  • Poolside bar
  • Concierge services
9.2 out of 10, Wonderful, (1008)
Sophisticated island elegance awaits at this Key West haven, where three refreshing pools invite endless relaxation. Spacious rooms feature deep soaking tubs and private balconies, while poolside dining creates memorable experiences. Located within walking distance of Mallory Square's waterfront attractions.
The price is S$387
includes taxes & fees
2 Dec - 3 Dec
The Marker Key West Harbor Resort
Fireplace
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4.0 star property
Old Town Key West
  • On private beach
  • Full-service spa
  • 2 outdoor pools
  • Concierge services
8.4 out of 10, Very good, (438)
Seaside sophistication unfolds across this historic Hilton resort featuring full-service Spa Al Mare offering beachfront massages and hydrotherapy. Sun-drenched days transition between private beach loungers, tropical pools, and sunset vistas from this elegant Key West sanctuary.
The price is S$439
includes taxes & fees
1 Dec - 2 Dec
Casa Marina Key West, Curio Collection by Hilton
3 outdoor pools, pool umbrellas, pool loungers
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4.0 star property
Old Town Key West
  • On the beach
  • Beachfront dining
  • Full-service spa
  • 2 poolside bars
  • Concierge services
8.6 out of 10, Excellent, (2864)
Seaside sophistication unfolds across 3 outdoor pools and a beachfront setting where pampering is paramount. Petite Spa offers couples' treatments and outdoor services, while pillowtop beds await in stylishly appointed rooms. Savour oceanview meals at the café after beach yoga or sunset cocktails.
The price is S$343
includes taxes & fees
2 Dec - 3 Dec
Southernmost Beach Resort and Guesthouses
View from room
H2O Suites - Adults Only

H2O Suites - Adults Only

3.5 star property
Old Town Key West
  • Near the beach
  • Poolside bar
  • Concierge services
  • Adults-only
9.8 out of 10, Exceptional, (578)
Luxurious tranquility awaits at this adults-only Key West sanctuary. Private balconies, plush pillowtop beds, and some suites with personal plunge pools create intimate retreats. Savour cocktails at the rooftop pool bar while South Beach and Hemingway's home beckon just steps away.
The price is S$599
includes taxes & fees
15 Dec - 16 Dec
H2O Suites - Adults Only
Front of property
Seashell Motel

Seashell Motel

1.5 star property
Old Town Key West
  • Near the beach
  • Concierge services
7.8 out of 10, Good, (1002)
Situated minutes from the shoreline, this recently remodeled Key West retreat combines luxury with convenience. Modern rooms feature refrigerators and updated bathrooms, while lush garden spaces provide peaceful relaxation after beach explorations. Bicycle rentals invite scenic coastal adventures.
The price is S$192
includes taxes & fees
24 Nov - 25 Nov
Seashell Motel
Terrace/patio
Southernmost House

Southernmost House

4.0 star property
Old Town Key West
  • Ocean-view dining
  • Poolside bar
  • Concierge services
  • Adults-only
9.4 out of 10, Exceptional, (1004)
Pampered elegance awaits at this historic Victorian retreat where the poolside bar serves drinks with stunning ocean views. Adults enjoy champagne service, pillowtop beds with premium linens, and complimentary breakfast at the Seaside Cafe before exploring nearby attractions.
The price is S$473
includes taxes & fees
16 Dec - 17 Dec
Southernmost House
Outdoor pool
Fairfield Inn & Suites by Marriott Key West at the Keys Collection

Fairfield Inn & Suites by Marriott Key West at the Keys Collection

3.5 star property
New Town
  • Poolside dining
  • Poolside bar
  • Concierge services
8.6 out of 10, Excellent, (1001)
289
The price is S$194
includes taxes & fees
1 Dec - 2 Dec
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Courtyard
Santa Maria Suites

Santa Maria Suites

4.0 star property
Old Town Key West
  • Poolside bar
  • Concierge services
9.6 out of 10, Exceptional, (1003)
Poolside bliss awaits at this upscale Key West resort steps from Duval Street and South Beach. Guests indulge in pillowtop beds, spacious suites with private balconies, and daily manager's receptions. The on-site restaurant Milagro serves dinner while 2 outdoor pools provide perfect relaxation spots.
The price is S$497
includes taxes & fees
1 Dec - 2 Dec
Santa Maria Suites
Exterior
Southwinds Motel

Southwinds Motel

2.0 star property
Old Town Key West
  • Near the beach
  • 2 outdoor pools
  • Concierge services
8.8 out of 10, Excellent, (1224)
Seaside elegance combines with island charm in this intimate hideaway. Luxuriate by 2 outdoor pools surrounded by loungers and tropical gardens, or indulge in sumptuous pillowtop beds with down comforters after exploring nearby South Beach.
The price is S$243
includes taxes & fees
8 Dec - 9 Dec
Southwinds Motel
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 Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Everyone was so friendly and helpful. The outside environment was absolutely amazing the paths the pool greenery just unspeakable.. wow and the spa massage omg.. loved it food was great the tours excellent and the roosters crowing lol💕"
Marcella 2-night trip
Posted 3 days ago
Pier House Resort & Spa

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Frequently asked questions

Are you searching for the perfect hotel for your luxury holiday in Key West?
Known for its ocean views and sunsets, Key West also has some interesting things to see and do including Duval Street, so you may want to take in the local sights during your visit.
What's the best high-end hotel in Key West?
Oceans Edge Key West Resort, Hotel & Marina is a luxury hotel with 6 outdoor pools and a marina, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Another upscale option for your trip is The Porch on Frances Inn.
When can I expect good weather in Key West?
Planning for the weather is a good way to make your trip to Key West relaxing and enjoyable, especially when you're splurging. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 23°C. Average annual precipitation for Key West is 956 mm.
What's there to see and do in Key West?
Experience Key West with a stop at Duval Street, Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. If you have spare time during your trip, you might want to make a stop at Harry S. Truman Little White House and Audubon House and Tropical Gardens.