The Florida Keys Travel Guide

26 Hotels

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1
  • luxury
  • dining
  • location

Little Palm Island Resort & Spa

$$$$ | MM 28.5 OS

There's a long list of notable guests that have chosen to spend time at Little Palm Island, and it's no wonder... Read More

  • luxury
  • dining
  • location

Little Palm Island Resort & Spa

$$$$ | MM 28.5 OS

There's a long list of notable guests that have chosen to spend time at Little Palm Island, and it's no wonder... Read More

2
  • luxury
  • dining

Sunset Key Cottages

$$$$ | 245 Front St.

Looking for a quiet, island getaway that will afford you pampering and privacy? Look no further. Read More

  • luxury
  • dining

Sunset Key Cottages

$$$$ | 245 Front St.

Looking for a quiet, island getaway that will afford you pampering and privacy? Look no further. Read More

3
  • 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

4
  • 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

5
  • luxury
  • dining
  • activities

Cheeca Lodge & Spa

$$ | MM 82 OS

See and be seen at Cheeca Lodge and Spa. Read More

  • luxury
  • dining
  • activities

Cheeca Lodge & Spa

$$ | MM 82 OS

See and be seen at Cheeca Lodge and Spa. Read More

6
  • dining
  • best for nightlife

Pier House Resort and Spa

$$$$ | 1 Duval St.

Marrying the best of Key West culture with modern conveniences, The Pier House Resort & Spa is perched on the... Read More

  • dining
  • best for nightlife

Pier House Resort and Spa

$$$$ | 1 Duval St.

Marrying the best of Key West culture with modern conveniences, The Pier House Resort & Spa is perched on the... Read More

7
  • luxury
  • activities

Postcard Inn Beach Resort & Marina at Holiday Isle

$$ | MM 84 OS

When you imagine the Florida Keys, this is the place that comes to mind, even if you’ve never been to these is... Read More

  • luxury
  • activities

Postcard Inn Beach Resort & Marina at Holiday Isle

$$ | MM 84 OS

When you imagine the Florida Keys, this is the place that comes to mind, even if you’ve never been to these is... Read More

8
  • dining
  • activities

Hawks Cay Resort

$$$ | Conch Key and 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

$$$ | Conch Key and Duck Key MM 61 OS

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

9
  • relaxing

Kona Kai Resort, Gallery & Botanic Gardens

$$ | MM 97.8 BS

Charming, in every way. Step out the door of your cottage and onto brick-paved walkways that lead to a private... Read More

  • relaxing

Kona Kai Resort, Gallery & Botanic Gardens

$$ | MM 97.8 BS

Charming, in every way. Step out the door of your cottage and onto brick-paved walkways that lead to a private... Read More

10
  • dining
  • best for nightlife

Margaritaville Key West Resort & Marina

$$$$ | 245 Front St.

The vibe isn’t "grapefruit and juicy fruit" yet at this former Westin-turned-Margaritaville, but the brand has... Read More

  • dining
  • best for nightlife

Margaritaville Key West Resort & Marina

$$$$ | 245 Front St.

The vibe isn’t "grapefruit and juicy fruit" yet at this former Westin-turned-Margaritaville, but the brand has... Read More

11
  • dining

Ocean Key Resort & Spa

$$$$ | Zero Duval St.

Luxury can be fun, especially when it’s at the edge of everything Key West. Even if you’re more of a watcher t... Read More

  • dining

Ocean Key Resort & Spa

$$$$ | Zero Duval St.

Luxury can be fun, especially when it’s at the edge of everything Key West. Even if you’re more of a watcher t... Read More

12
  • relaxing

Coconut Bay Resort & Bay Harbor Lodge

$ | MM 97.7 BS

Get an authentic taste of island life at these sister properties that offer everything you need to disconnect... Read More

  • relaxing

Coconut Bay Resort & Bay Harbor Lodge

$ | MM 97.7 BS

Get an authentic taste of island life at these sister properties that offer everything you need to disconnect... Read More

13
  • dining

The Islander, A Guy Harvey Outpost Resort

$$ | MM 82.1 OS

Imagine a beloved resort built in 1950, on 20+ oceanfront acres. Now, imagine updated, comfortable rooms, p... Read More

  • dining

The Islander, A Guy Harvey Outpost Resort

$$ | MM 82.1 OS

Imagine a beloved resort built in 1950, on 20+ oceanfront acres. Now, imagine updated, comfortable rooms, p... Read More

14
  • dining
  • activities

Amy Slate's Amoray Dive Resort

$ | MM 104.2 BS

With the words ‘dive resort’ in the name, you can bet that this property is set up to function... Read More

  • dining
  • activities

Amy Slate's Amoray Dive Resort

$ | MM 104.2 BS

With the words ‘dive resort’ in the name, you can bet that this property is set up to function... Read More

15
  • authentic

Gulf View Waterfront Resort

$ | MM 58.7 BS

This family run resort caters to its guests and their pets. They’re on the Gulf of Mexico, the units are clean... Read More

  • authentic

Gulf View Waterfront Resort

$ | MM 58.7 BS

This family run resort caters to its guests and their pets. They’re on the Gulf of Mexico, the units are clean... Read More

B 16

Baker's Cay Resort Key Largo, Curio Collection by Hilton

$$$ | 97000 Overseas Hwy.

Nestled within a “hardwood hammock” (localese for uplands habitat where hardwood trees such as live oak grow)... Read More

Baker's Cay Resort Key Largo, Curio Collection by Hilton

$$$ | 97000 Overseas Hwy.

Nestled within a “hardwood hammock” (localese for uplands habitat where hardwood trees such as live oak grow)... Read More

C 17

Chesapeake Beach Resort

$$ | 83409 Overseas Hwy.

Modern conveniences and a retro look are among the hallmarks of this boutique hotel on the beach. Rooms have a... Read More

Chesapeake Beach Resort

$$ | 83409 Overseas Hwy.

Modern conveniences and a retro look are among the hallmarks of this boutique hotel on the beach. Rooms have a... Read More

G 18

Grassy Flats

$$ | Grassy Key 58182 Overseas Hwy.

Owned by retired professional kiteboarder Matt Sexton, this relaxed, eco-friendly resort and beach club is pop... Read More

Grassy Flats

$$ | Grassy Key 58182 Overseas Hwy.

Owned by retired professional kiteboarder Matt Sexton, this relaxed, eco-friendly resort and beach club is pop... Read More

I 19

Isla Bella Beach Resort

$$ | 1 Knights Key Blvd.

Combining Caribbean luxury with Keys charm, this glamorous 24-acre resort is a destination unto itself with fi... Read More

Isla Bella Beach Resort

$$ | 1 Knights Key Blvd.

Combining Caribbean luxury with Keys charm, this glamorous 24-acre resort is a destination unto itself with fi... Read More

L 20

La Siesta Resort & Marina

$$$ | 80241 Overseas Hwy.

With 6 acres of oceanfront property, accommodations that range from studio units to a glamorous three-bedroom... Read More

La Siesta Resort & Marina

$$$ | 80241 Overseas Hwy.

With 6 acres of oceanfront property, accommodations that range from studio units to a glamorous three-bedroom... Read More

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