Deals on vacations and trips to Fleming Key

Save when you book Fleming Key package deals

Choose two or more items and save on your trip:

Fleming Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $814, price is now $386 per person
$386
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $1,624, price is now $664 per person
$664
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Price was $1,643, price is now $750 per person
$750
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This apartment features an outdoor pool and a 24-hour gym. WiFi in public areas is free. Valet parking and a safe deposit box are also offered on site.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $17,468, price is now $8,290 per person
$8,290
per person
Jan 14 - Jan 18
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $961, price is now $465 per person
$465
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.

Top Fleming Key hotels deals

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$208 nightly
The price is $234 total per night
$234 total
Nov 16 - Nov 17
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Pool
Pet friendly
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$157 nightly
The price is $177 total per night
$177 total
Nov 17 - Nov 18
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Pool
Hot Tub
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$193 nightly
The price is $217 total per night
$217 total
Nov 17 - Nov 18
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.
On private beach
Pool
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Free Cancellation
$242 nightly
The price is $272 total per night
$272 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Pool
Spa
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$235 nightly
The price is $264 total per night
$264 total
Dec 2 - Dec 3
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.
Pool
Pet friendly
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
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $126 total per night
$126 total
Dec 1 - Dec 2
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like a free area shuttle.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Fleming Key
View all properties
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.

Frequently asked questions

How much are vacation packages to Fleming Key?
Vacation packages, which include flights and hotels in Fleming Key, start from just $386. Make your travel dreams a reality and secure your vacation with Travelocity today.
Where can I get the best vacation package deals for Fleming Key?
One word — Travelocity. With no less than 400 partner airlines and 1,000,000 properties across the globe, it's a breeze to craft a Fleming Key package deal that fits your budget.
Why should I book my Fleming Key vacation bundle via Travelocity?
Nothing beats the feeling of knowing you've bagged the best price available — that's our Price Match Guarantee. Add to that our enormous range of destinations and 24/7 team of customer service professionals and you've got the formula for an unforgettable vacation.
Can I save on my Fleming Key car rental if I bundle it with my hotel or flight?
Certainly — and if you also add a tour to your Fleming Key vacation package, you'll pick up even greater savings. With an affordable package from Travelocity, you can find things to do around the region that interest you. Then, jump in your rental car and work your way through the list. Zoo Miami is one terrific sight to put on your itinerary. It's 110 mi from Fleming Key.
What is the best time of year to go to Fleming Key?
If you really want to wander wisely, is one of the best times to do it. That's when hotel rates are at their cheapest. In contrast, prices are at their highest around . January, February and March are the most popular times to vacation in Fleming Key, so expect long queues for famous attractions. Rather avoid the busy season? You'll find fewer crowds during August, September and October.

Photos of local treasures

Browse Fleming Key vacation photos for more inspiration

Explore More Ways to Travel with Travelocity