Fleming Key Vacation Packages 2026 from $495

Fleming Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Casablanca Miami Beach

North Beach

$495

per person

Apr 8 - Apr 14

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.

Miami Downtown Condos

Downtown Miami

$967

per person

Mar 26 - Mar 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free condo includes 2 restaurants, an outdoor pool, and a 24-hour gym. Business travelers can take advantage of the business center. A poolside bar, a 24-hour front desk, and a coffee shop are also provided.

Creekside Inn

$836

per person

Mar 27 - Apr 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,341

per person

Mar 23 - Mar 27

found 1 day 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.

Solé Miami, A Noble House Resort

Ocean Four

$518

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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 and an off-leash area. Enjoy the 24-hour gym and unwind at the beach bar and poolside bar.

Top Fleming Key hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$530 nightly

$596 total

Jan 26 - Jan 27

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 on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$560 nightly

$630 total

Feb 8 - Feb 9

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.

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$436 nightly

$491 total

Jan 25 - Jan 26

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 picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$430 nightly

$484 total

Jan 25 - Jan 26

Total with taxes and fees

This smoke-free hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Unwind with a drink at the bar/lounge and enjoy perks like a free beach shuttle.

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$258 nightly

$290 total

Jan 22 - Jan 23

Total with taxes and fees

This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$401 nightly

$451 total

Jan 25 - Jan 26

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.

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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 $495. 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.