Fleming Key Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Beach vacation packages in Fleming Key

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

Bay Breeze Premium Apartments By Eskape Collection

Save 100% on your flight

$629

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (238 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,839

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$959

per person

Nov 6 - Nov 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,180 reviews)

When we first arrived at the hotel the staff Clariza or Clarisa was very rude and disrespectful. She told us about a reservation fee and I asked for more clarification regarding that fee. She got smart and snatched the card and said it’s $165 along with a $250 deposit.

Reviewed on Sep 15, 2026

1 Hotel South Beach

South Beach

$3,500

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,617 reviews)

EAST Miami Residences

Brickell

Save 100% on your flight

$1,292

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (150 reviews)

The room was really nice, there are small things that can be improved but overall nice.

Reviewed on Aug 25, 2026

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

5* Beach vacations in Fleming Key

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

EAST Miami Residences

Brickell

Save 100% on your flight

$1,292

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (150 reviews)

The room was really nice, there are small things that can be improved but overall nice.

Reviewed on Aug 25, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,839

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

1 Hotel South Beach

South Beach

$3,500

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,617 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

3 Night Beach vacations in Fleming Key

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

Pelican Hotel

South Beach

Save 100% on your flight

$509

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (506 reviews)

nanana

Reviewed on Sep 14, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,839

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

1 Hotel South Beach

South Beach

$3,500

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,617 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

4 Night Beach vacations in Fleming Key

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

Barcelona Studios Guesthouse

South Beach

Save 100% on your flight

$310

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (258 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,804

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

President Hotel Villa

South Beach

Save 100% on your flight

$902

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,004 reviews)

I love the room. I would definitely stay again. The only thing I would say is the showers are definitely not hot enough for me. I don’t know if I just like it too hot but that’s the only issue I really had.

Reviewed on Sep 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

How do I book the best Fleming Key beach vacation packages?

Life’s a beach when you dive into our brilliant Fleming Key beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Fleming Key?

A rental steps from the shore creates an amazingly affordable Fleming Key beach vacation. Seaside sojourns during low season start from $310. Prices and availability are subject to change. Additional terms may apply.

When should I book a Fleming Key beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Fleming Key?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Fleming Key beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Fleming Key vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Fleming Key beach vacation deals?

Sort your search results by deals to delight in amazing Fleming Key beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Fleming Key beach trip with free cancellation and/or flexible dates?

Just like the Fleming Key tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Fleming Key beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Fleming Key. (OK, maybe not that last part.)