Fleming Key Beach Vacations

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Top Beach vacation packages in Fleming Key

Price found within the past 48 hours. Click for updated prices.
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was $1,519, price is now $635 per person
$635
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
2/10 (2 reviews)
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 $22,228, price is now $11,336 per person
$11,336
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
6080 Design Hotel by Eskape Collection

6080 Design Hotel by Eskape Collection

4 out of 5
Mid Beach
Save 100% on your flight
Price was $1,756, price is now $1,022 per person
$1,022
per person
Jun 24 - Jul 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
Great location, super clean and modern.

Reviewed on May 9, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
Save 100% on your flight
Price was $1,759, price is now $1,043 per person
$1,043
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (192 reviews)
The resort, staff and facilities are excellent. The location in Islamorada is great either for a few days in the keys or as a stopping point to or from Key West. We didn’t get time to use all of the facilities but there are restaurants on site, kayaks, pools, a lively beach and breakfast so you don’t have to leave if you don’t want to.

Reviewed on May 10, 2026

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Save 100% on your flight
Price was $1,397, price is now $843 per person
$843
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (464 reviews)
Loved the location in the middle of the art deco district. All staff were pleasant & helpful. Meals at restaurant were delicious.

Reviewed on May 5, 2026

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5* Beach vacations in Fleming Key

Price found within the past 48 hours. Click for updated prices.
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was $1,519, price is now $635 per person
$635
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
2/10 (2 reviews)
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 $22,228, price is now $11,336 per person
$11,336
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was $2,278, price is now $1,407 per person
$1,407
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,501 reviews)
Don’t even think— just book it! Loved this property and all of its amenities!

Reviewed on May 8, 2026

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See all available trips from Columbus to Fleming Key
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3 Night Beach vacations in Fleming Key

Price found within the past 48 hours. Click for updated prices.
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was $1,519, price is now $635 per person
$635
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
2/10 (2 reviews)
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 $18,188, price is now $9,210 per person
$9,210
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (1 review)
Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Save 100% on your flight
Price was $1,700, price is now $955 per person
$955
per person
Jul 17 - Jul 20
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (151 reviews)
This was an overall excellent experience. The room was nice and reasonably priced. There ended up being an ac issue where the room temperature wouldn’t drop below 77 degrees, which produced several sleepless nights. The communication with the rental temp was pretty horrid, we received a few ineffective ways to troubleshoot it; but nothing was ever fixed. We were even promised a follow up phone call the next day(post checkout) and were ghosted. This was pretty disappointing.

Reviewed on May 9, 2026

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4 Night Beach vacations in Fleming Key

Price found within the past 48 hours. Click for updated prices.
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was $1,899, price is now $679 per person
$679
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
6/10 (2 reviews)
3BR Pool House Sleeps 8

3BR Pool House Sleeps 8

3 out of 5
Driftwood
Price was $2,195, price is now $822 per person
$822
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
No reviews
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $4,875, price is now $2,146 per person
$2,146
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
5.8/10 (323 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

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Find your perfect Fleming Key beach vacation

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 $635. 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.)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.