The Florida Keys Travel Guide

20 Hotels

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1
  • dining
  • relaxing

The Reach, A Waldorf Astoria Resort

$$$ | 1435 Simonton St.

You might never know it’s there unless you stumble to the quiet end of Duval and wander down a side street tha... Read More

  • dining
  • relaxing

The Reach, A Waldorf Astoria Resort

$$$ | 1435 Simonton St.

You might never know it’s there unless you stumble to the quiet end of Duval and wander down a side street tha... Read More

2
  • luxury
  • dining
  • best for nightlife
  • relaxing

Casa Marina, A Waldorf-Astoria Resort

$$$ | 1500 Reynolds St.

If you’ve got the money, honey, this resort delivers. History buffs will relish in its storied past, and afflu... Read More

  • luxury
  • dining
  • best for nightlife
  • relaxing

Casa Marina, A Waldorf-Astoria Resort

$$$ | 1500 Reynolds St.

If you’ve got the money, honey, this resort delivers. History buffs will relish in its storied past, and afflu... Read More

3
  • relaxing

The Southernmost House

$$$ | 1400 Duval Street

This Victorian beauty is perhaps the most photographed home in Key West, for good reason. It just oozes tropic... Read More

  • relaxing

The Southernmost House

$$$ | 1400 Duval Street

This Victorian beauty is perhaps the most photographed home in Key West, for good reason. It just oozes tropic... Read More

4
  • dining
  • activities

Hawks Cay Resort

$$$ | Duck Key MM 61 OS

Hawks Cay is an island unto itself, a sprawling playground for adults and families alike. Read More

  • dining
  • activities

Hawks Cay Resort

$$$ | Duck Key MM 61 OS

Hawks Cay is an island unto itself, a sprawling playground for adults and families alike. Read More

5
  • relaxing

Parrot Key Resort

$$$ | 2801 N Roosevelt Blvd.

From the busy road, you can’t see much, just a long driveway leading to a resort that is nowhere near... Read More

  • relaxing

Parrot Key Resort

$$$ | 2801 N Roosevelt Blvd.

From the busy road, you can’t see much, just a long driveway leading to a resort that is nowhere near... Read More

6
  • location

Deer Run Bed & Breakfast

$$$ | MM 33 OS

Need serenity now? Find your way to this oceanfront B&B that not only will be good for your soul, it wi... Read More

  • location

Deer Run Bed & Breakfast

$$$ | MM 33 OS

Need serenity now? Find your way to this oceanfront B&B that not only will be good for your soul, it wi... Read More

7
  • best for nightlife

La Concha Hotel & Spa

$$$ | 430 Duval St.

Historic properties always have their quirks, and La Concha is no exception, but Read More

  • best for nightlife

La Concha Hotel & Spa

$$$ | 430 Duval St.

Historic properties always have their quirks, and La Concha is no exception, but Read More

8

The Caribbean Resort

$$$ | 117 South Carroll Street

Many resorts tout that they are your "home away from home," but The Caribbean Resort delivers like few can. Re... Read More

The Caribbean Resort

$$$ | 117 South Carroll Street

Many resorts tout that they are your "home away from home," but The Caribbean Resort delivers like few can. Re... Read More

9
  • best for nightlife

NYAH: Not Your Average Hotel

$$$ | 420 Margaret St.

Traveling for a girls’ getaway? Or a "mancation" with the bros? This is the affordable place to lay your head.... Read More

  • best for nightlife

NYAH: Not Your Average Hotel

$$$ | 420 Margaret St.

Traveling for a girls’ getaway? Or a "mancation" with the bros? This is the affordable place to lay your head.... Read More

A 10

Ambrosia Key West

$$$ | Key West 615, 618, 622 Fleming St.

If you desire personal attention, a casual atmosphere, and a dollop of style, stay at these twin inns spread o... Read More

Ambrosia Key West

$$$ | Key West 615, 618, 622 Fleming St.

If you desire personal attention, a casual atmosphere, and a dollop of style, stay at these twin inns spread o... Read More

C 11

Casa Morada

$$$ | Upper Matecumbe Key 136 Madeira Rd.

This relic from the 1950s has been restyled into a suave, design-forward, all-suites property with outdoor sho... Read More

Casa Morada

$$$ | Upper Matecumbe Key 136 Madeira Rd.

This relic from the 1950s has been restyled into a suave, design-forward, all-suites property with outdoor sho... Read More

I 12

Island City House Hotel

$$$ | Key West 411 William St.

A private garden with brick walkways, tropical plants, and a canopy of palms sets this convivial guesthouse ap... Read More

Island City House Hotel

$$$ | Key West 411 William St.

A private garden with brick walkways, tropical plants, and a canopy of palms sets this convivial guesthouse ap... Read More

M 13

Marquesa Hotel

$$$ | Key West 600 Fleming St.

In a town that prides itself on its laid-back luxury, this complex of four restored 1884 houses stands out. Gu... Read More

Marquesa Hotel

$$$ | Key West 600 Fleming St.

In a town that prides itself on its laid-back luxury, this complex of four restored 1884 houses stands out. Gu... Read More

M 14

Marriott's Key Largo Bay Beach Resort

$$$ | Key Largo 103800 Overseas Hwy.

This 17-acre bay-side resort has plenty of diversions, from diving to parasailing to a day spa. Given all that... Read More

Marriott's Key Largo Bay Beach Resort

$$$ | Key Largo 103800 Overseas Hwy.

This 17-acre bay-side resort has plenty of diversions, from diving to parasailing to a day spa. Given all that... Read More

O 15

Ocean House

$$$ | Windley Key 82885 Old Hwy.

This adults-only boutique hotel is situated right on the Atlantic, yet it's hidden from passersby amid lush ga... Read More

Ocean House

$$$ | Windley Key 82885 Old Hwy.

This adults-only boutique hotel is situated right on the Atlantic, yet it's hidden from passersby amid lush ga... Read More

P 16

Playa Largo Resort and Spa, Autograph Collection

$$$ | Key Largo 97450 Overseas Hwy.

This luxurious retreat, the first new hotel in Key Largo in over 21 years, is nestled on 14½ bay-front acres.... Read More

Playa Largo Resort and Spa, Autograph Collection

$$$ | Key Largo 97450 Overseas Hwy.

This luxurious retreat, the first new hotel in Key Largo in over 21 years, is nestled on 14½ bay-front acres.... Read More

S 17

Simonton Court

$$$ | Key West 320 Simonton St.

A small world all its own, this adults-only B&B makes you feel deliciously sequestered from Key West's cra... Read More

Simonton Court

$$$ | Key West 320 Simonton St.

A small world all its own, this adults-only B&B makes you feel deliciously sequestered from Key West's cra... Read More

S 18

Southernmost Beach Resort

$$$ | Key West 1319 Duval St.

Rooms at this hotel on the quiet end of Duval—a 20-minute walk from downtown—are modern and sophisticated, far... Read More

Southernmost Beach Resort

$$$ | Key West 1319 Duval St.

Rooms at this hotel on the quiet end of Duval—a 20-minute walk from downtown—are modern and sophisticated, far... Read More

M 19

The Marker

$$$ | Key West 200 William St.

As the first new hotel to open in Key West since the early 1990s, The Marker is a welcome and luxurious additi... Read More

The Marker

$$$ | Key West 200 William St.

As the first new hotel to open in Key West since the early 1990s, The Marker is a welcome and luxurious additi... Read More

P 20

Pearl's Rainbow

$$$ | Key West 525 United St.

This guesthouse—which once catered only to lesbians and gay-friendly women—is now open to everyone. Set in an... Read More

Pearl's Rainbow

$$$ | Key West 525 United St.

This guesthouse—which once catered only to lesbians and gay-friendly women—is now open to everyone. Set in an... Read More

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