Key Haven Beach Vacations

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Top Beach vacation packages in Key Haven

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

The Perry Hotel & Marina Key West

Save 100% on your flight

$1,051

per person

Oct 7 - Oct 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,335 reviews)

Parrot Key Hotel & Villas

Northside Resort

$1,396

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,455 reviews)

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,783

per person

Nov 21 - Nov 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Southernmost House - Adult Exclusive

Old Town Key West

$2,010

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,004 reviews)

We were on the top floor. Lots of stairs. Make sure you can do stairs when booking or request a lower floor. It's beautiful, great location and would go back again.

Reviewed on Sep 1, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$2,091

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.8/10 Excellent! (3,534 reviews)

The resort fee is very expensive for what the resort has to offer for the guests. I will not rebook this resort the next time we are in Keywest. No shuttle services are offered. Nothing complimentary but two welcome drinks.

Reviewed on Sep 1, 2026

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3 Night Beach vacations in Key Haven

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

The Perry Hotel & Marina Key West

$1,164

per person

Nov 4 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,335 reviews)

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,370

per person

Nov 4 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,004 reviews)

We were on the top floor. Lots of stairs. Make sure you can do stairs when booking or request a lower floor. It's beautiful, great location and would go back again.

Reviewed on Sep 1, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,424

per person

Nov 4 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.8/10 Excellent! (3,534 reviews)

Reviewed on Sep 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Key Haven

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4 Night Beach vacations in Key Haven

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

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

$583

per person

Oct 26 - Oct 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (985 reviews)

Great boutique hotel! The room was clean, the bed was very comfortable, and the location was perfect—just one block from Duval Street, with restaurants nearby. Breakfast was also better than I expected! Live music by the pool (afternoon and during breakfast) and at night was very quiet! Overall, a very pleasant stay!

Reviewed on Aug 30, 2026

Parrot Key Hotel & Villas

Northside Resort

$1,396

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,455 reviews)

The Key West Hotel

Key West Historic District

$2,903

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

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

Life’s a beach when you dive into our brilliant Key Haven 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 Key Haven?

A rental steps from the shore creates an amazingly affordable Key Haven beach vacation. Seaside sojourns during low season start from $583. Prices and availability are subject to change. Additional terms may apply.

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

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 Key Haven 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 Key Haven 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 Key Haven beach vacation deals?

Sort your search results by deals to delight in amazing Key Haven 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 Key Haven beach trip with free cancellation and/or flexible dates?

Just like the Key Haven 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 Key Haven 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 Key Haven. (OK, maybe not that last part.)

Top Beach Key Haven Hotels

Floralee House in Key West

Key West FL

11 min drive from Duval Street

Stay at this vacation home in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Smathers Beach are located nearby.

Private & Haven-ly - Pool Home on Boating Canal

Key Haven FL

11 min drive from Duval Street

Stay at this vacation home in Key West. Enjoy laundry facilities, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Duval Street and ...

See all 3,109 properties in Key Haven

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.