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Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
  • 29 min drive from Florida Keys Beaches
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,320 reviews)
"It was a peaceful location that was still in walking distance to a Starbucks & McDonald's. It offered a free shuttle, & we selected a room with an ocean view where we were able to capture breathtaking photos. The room was spacious. The beds were extremely uncomfortable & noisy."

Reviewed on Jul 3, 2026

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
  • 30 min drive from Florida Keys Beaches
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
  • 36 min drive from Florida Keys Beaches
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (3,410 reviews)
"Got a wonderful upgrade. Staff very friendly and helpful."

Reviewed on Jul 3, 2026

Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
  • 29 min drive from Florida Keys Beaches
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
8/10 Very Good! (1,260 reviews)
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Reviewed on Jul 3, 2026

Hilton Garden Inn Key West / The Keys Collection
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
  • 37 min drive from Florida Keys Beaches
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,208 reviews)
"Great location! Enjoyed the private beach and location walkable to shops and dining. Staff was very friendly!"

Reviewed on Jul 3, 2026

Pier House Resort & Spa
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
  • 33 min drive from Florida Keys Beaches
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,802 reviews)
"Our room was relatively clean, but the shower didn’t drain. I really appreciated the concierge for her help, and the shuttle service was awesome. Overall it was a pretty alright hotel. I probably wouldn’t stay again, but I don’t really have complaints."

Reviewed on Jul 3, 2026

Margaritaville Beach House Key West
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
  • 35 min drive from Florida Keys Beaches
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Southernmost Point and Duval ...
8.6/10 Excellent! (736 reviews)
"Beautiful property and great location! We had a great time and would definitely come back!"

Reviewed on Jul 3, 2026

Casa Marina Key West, Curio Collection by Hilton
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
  • 31 min drive from Florida Keys Beaches
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
9/10 Wonderful! (1,810 reviews)
"What an amazing experience. Can’t wait to come back!"

Reviewed on Jul 3, 2026

Havana Cabana at Key West
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
  • 30 min drive from Florida Keys Beaches
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,168 reviews)
"Everything was excellent from the rooms to the pool. Even the outsides grounds was excellent."

Reviewed on Jul 3, 2026

Hyatt Vacation Club at Windward Pointe, Key West
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St Key West FL
  • 37 min drive from Florida Keys Beaches
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (431 reviews)
"I stay here anytime I’m in KW, love this resort and the customer service is great!! I’ll be back soon!"

Reviewed on Jun 25, 2026

La Concha Key West, Autograph Collection
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
  • 28 min drive from Florida Keys Beaches
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
9.4/10 Exceptional! (1,282 reviews)
"The staff was very friendly and the pool was amazing. The shuttle was an extra bonus. Great Stay and will return!"

Reviewed on Jul 2, 2026

The Perry Hotel & Marina Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
  • 29 min drive from Florida Keys Beaches
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,045 reviews)
"We were pleasantly impressed with this hotel. Staff were excellent, everything was clean and well run. Great value for money in this part of the US."

Reviewed on Jul 2, 2026

DoubleTree Resort by Hilton Grand Key - Key West
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.

Find cheap hotels in Fleming Key

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Fleming Key hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Fleming Key.

Choosing the right hotel in Florida has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Fleming Key’s 2,732 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $155. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Fleming Key hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Fleming Key. No matter your reason for visiting Fleming Key, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Fleming Key hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Fleming Key for as low as $155.

How many hotels are there in Fleming Key?

With over 2,732 hotels in Fleming Key, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $155.

How to find cheap car rentals in Fleming Key?

Finding a cheap car rental deal in Fleming Key is as easy as scoring cheap hotels in Fleming Key. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.