Key Haven Cheap Vacations

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Top Cheap vacation packages in Key Haven

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

$887

per person

Nov 29 - Dec 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

The room was perfectly clean and comfortable. However, our experience with the staff was a bit mixed. While some of the bartenders were incredibly friendly and welcoming, a few others could definitely use some training in hospitality and politeness. Additionally, it would be great if breakfast hours could be extended a bit later. When people are on vacation, they want to sleep in without worrying about missing the morning meal!

Reviewed on Oct 25, 2026

Southernmost House - Adult Exclusive

Old Town Key West

$1,903

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

staff was super friendly and accomodating

Reviewed on Oct 22, 2026

The Marker Key West Harbor Resort

Key West Historic District

$1,013

per person

Nov 29 - Dec 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

Love this place!!!

Reviewed on Oct 24, 2026

The Gardens Hotel

Old Town Key West

$1,331

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto

Reviewed on Oct 20, 2026

Parrot Key Hotel & Villas

Northside Resort

$2,169

per person

Dec 26 - Dec 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,468 reviews)

This was a VERY clean property. Literally bleach cleaned OUTSIDE to keep bugs and critters at bay, and very well maintained grounds. The sand along the water front was groomed daily! The onsite eatery was under reconstruction and they had a pop up option in the grounds poolside, in addition to a food truck in the front parking area. It was pretty convenient. Cleaning was every other day, and fresh towels were offered daily. Loved the serenity, the water views and being off of Duval. Will be back again.

Reviewed on Oct 24, 2026

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3 Night Cheap vacations in Key Haven

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,838

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

Reviewed on Oct 25, 2026

The Marker Key West Harbor Resort

Key West Historic District

$1,986

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

Love this place!!!

Reviewed on Oct 24, 2026

The Gardens Hotel

Old Town Key West

$2,119

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto

Reviewed on Oct 20, 2026

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4 Night Cheap vacations in Key Haven

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

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West

$2,189

per person

Nov 30 - Dec 4

found 9 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Key West (EYW)

10/10 Exceptional! (3 reviews)

Loved it

Reviewed on Mar 20, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,880

per person

Dec 27 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (564 reviews)

Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

Save 100% on your flight

$3,176

per person

Jan 16 - Jan 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

10/10 Exceptional! (1 review)

Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

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How can I find budget-friendly Key Haven vacation packages on Expedia?

Playing around with the easy-to-use search wizard is one of the best ways to find affordable Key Haven vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest Key Haven getaways within seconds. You can also use the maximum price filter to view deals within your budget. If you're traveling during peak season dates, it's a good idea to book early to snag some of the best offers. You may score irresistible last-minute specials for travel in low season.

How to find cheap last-minute Key Haven travel deals?

On Expedia's last-minute travel deals page, you'll encounter a plethora of special offers for late vacations to Key Haven. Remember, you're more likely to bag savings on last-minute travel during off-peak periods. Consider checking different departure dates, too. Expedia's nifty search tool lets you compare some of the best last-minute Key Haven vacation packages. The handy filters let you tailor your trip according to your preferences, including hotel star rating, amenities, and property location.

When is the best time to visit Key Haven on a budget?

For some of the cheapest vacation packages to Key Haven from $887, it's best to travel during low season dates. With fewer people traveling during these periods, flights and hotels usually have lower prices. It's also a good idea to avoid popular travel times. These include spring break, Thanksgiving, and other federal holidays. On Expedia, you'll encounter some of the best travel deals to Key Haven. Best of all, vacation payment plans mean you can spread the cost of your trip over 3, 6, or 12 months.

Can I cancel my Key Haven vacation package booking?

Yes, many of Expedia's cheap Key Haven getaway packages allow for free cancellation in case your plans change. Follow the easy steps to cancel by logging into your Expedia account and clicking on “Trips” page'. Keep in mind, though, that each vacation package has different cancellation policies, so be sure to look over them before booking. The good news is you'll clearly see this information on Expedia when you book. There's even a free cancellation search filter that lets you view flexible vacations to Key Haven.

Why should I book my Key Haven vacation with Expedia?

A multitude of exclusive travel deals you won't find anywhere else is one of the top reasons to book your cheap Key Haven vacation package with Expedia. And with one of the widest choices of flights and hotels available, you'll easily find the right trip for you. The handy search wizard and filters let you compare hundreds of great deals in seconds, too. It's not only the cheap prices either: Expedia's booking protection and 24/7 support give you peace of mind before and during your 2026 trip.

How to find cheap Key Haven vacation packages on Expedia?

When searching for budget vacations to Key Haven, look out for the green savings label. This indicates you've snagged a deal only available on Expedia. Another popular way of getting money off your 2026Key Haven vacation is by joining One Key. Expedia's amazing reward program gives you access to hundreds of member-only discounts on select hotels. Keep a look out for the blue savings label in the search results. Best of all, One Key is free to join.

Why should I book a package to Key Haven?

You'll often snag package savings on your Key Haven vacation when bundling together your flights and accommodation. Expedia even shows you how much you're saving by booking a package. It's not just cheaper prices, either. Packages often have more flexible booking conditions, meaning you're more likely to get a refund in case your 2026 plans change. While booking flights and hotels separately usually requires full payment, Key Haven vacation packages often let you pay a small upfront deposit to confirm.

How to plan a cheap vacation to Key Haven?

Settling on your dates is usually the first step to planning an affordable Key Haven getaway. If you're traveling during peak season dates, it's a good idea to book your trip in advance. This way, you're more likely to bag early-bird deals. Don't rule out a last-minute travel deal for low season dates, though. Once you've picked your dates, tap them into the search wizard to see some of the best Key Haven vacation package deals. Hop over to Expedia's vacation planning page for more tips for your dream vacation.