Top Beach vacation packages in Key Haven

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

Oceans Edge Key West Resort, Hotel & Marina

$1,287

per person

Jun 21 - Jun 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,825 reviews)

The pools were very nice, breakfast was excellent, only thing they can do different is have some outdoor entertainment at the pool area

Reviewed on Apr 1, 2026

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,569

per person

Jun 21 - Jun 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,194 reviews)

Second time we have stayed here.Staff is excellent, accommodating. The property is very well maintained and a great location.

Reviewed on Apr 1, 2026

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,763

per person

Jun 21 - Jun 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (572 reviews)

Beach is beautiful.

Reviewed on Apr 1, 2026

The Perry Hotel & Marina Key West

$1,370

per person

Jun 21 - Jun 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,226 reviews)

great variety on the menus. we enjoyed our stay. My only negative comment is related to the loud conversations of our neighbors on the balcony two days and also a couple were sitting by the fire pits while they were on a phone call that they put on speaker. These incidents made our time relaxing on the balcony less enjoyable.

Reviewed on Mar 28, 2026

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

$1,535

per person

Jun 13 - Jun 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,011 reviews)

We stayed at the Marker for our anniversary in a Harbor View room. Room was very nice and we looked out over a marina and had a nice balcony to sit out and enjoy a glass of wine. Breakfast was good at the bar by the pool but not great. Staff very friendly and helpful. Good enough fitness room to get a decent workout in but no universal machines. Close enough to walk to just about anything you need. If you do stay in the Herbirview room be aware that the Schooner Bar across the path plays music til around 11 am or later each night and you can hear it from your room though it’s muffled. The first night we were there the band playing was way too loud and I could hear the words of the songs inside my room while the door was closed. But if you want a very nice hotel with 3 pools and attentive staff in a great location whilst having the Key West vibe all around you the Marker is very good.

Reviewed on Apr 1, 2026

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3 Night Beach vacations in Key Haven

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

Oceans Edge Key West Resort, Hotel & Marina

$852

per person

Jun 13 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,825 reviews)

The pools were very nice, breakfast was excellent, only thing they can do different is have some outdoor entertainment at the pool area

Reviewed on Apr 1, 2026

The Marker Key West Harbor Resort

Key West Historic District

$1,087

per person

Jun 13 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,011 reviews)

We stayed at the Marker for our anniversary in a Harbor View room. Room was very nice and we looked out over a marina and had a nice balcony to sit out and enjoy a glass of wine. Breakfast was good at the bar by the pool but not great. Staff very friendly and helpful. Good enough fitness room to get a decent workout in but no universal machines. Close enough to walk to just about anything you need. If you do stay in the Herbirview room be aware that the Schooner Bar across the path plays music til around 11 am or later each night and you can hear it from your room though it’s muffled. The first night we were there the band playing was way too loud and I could hear the words of the songs inside my room while the door was closed. But if you want a very nice hotel with 3 pools and attentive staff in a great location whilst having the Key West vibe all around you the Marker is very good.

Reviewed on Apr 1, 2026

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

$931

per person

Jun 13 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (572 reviews)

Beach is beautiful.

Reviewed on Apr 1, 2026

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4 Night Beach vacations in Key Haven

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$938

per person

Jun 4 - Jun 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,194 reviews)

Second time we have stayed here.Staff is excellent, accommodating. The property is very well maintained and a great location.

Reviewed on Apr 1, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,301

per person

Jun 19 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (536 reviews)

The tag line of the hotel is "Come Hide" which was appropriate as it is hidden from plain view of the hustle and bustle of Duval St. The entrance is mysterious as it is set back and the pathway leading to the reception office is filled with green ferns/palms. Loved it! The center of the property is highlighted the bar and the permanent stage for the daily entertainment. Great place to stay and close to everything!

Reviewed on Mar 30, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,138

per person

Jun 19 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,020 reviews)

Room was very spacious and clean!

Reviewed on Mar 30, 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 $852. Prices and availability are subject to change. Additional terms may apply.

When should I book a Key Haven 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 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?

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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 3,068 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.