Key Haven Cheap Vacations

Book a 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 Cheap vacation packages in Key Haven

Price found within the past 48 hours. Click for updated prices.
  • Jan 21 - Jan 25

    Blue Flamingo Resort Key West + Flight

    New Town
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,785 reviews)
    "They have open passes for non paying people/locals on the weekend. Couldn't get a pool chair very crowed and screaming kids running around. Bill is incorrect too. Room didn't get cleaned Not happy ."
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - FLL • Nonstop MIA - BOS • Nonstop
    $1,231
    $895
    per traveler
    found 1 day ago
    Blue Flamingo Resort Key West
  • Dec 23 - Dec 28

    The Key West Hotel + Flight

    Key West Historic District
    5 nights
    3.0 star property
    9.2/10 - Wonderful (565 reviews)
    "Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!"
    Reviewed October 29, 2026
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - EYW • Nonstop EYW - BOS • 1 stop
    $3,773
    $2,370
    per traveler
    found 1 day ago
    The Key West Hotel
  • Dec 23 - Dec 28

    Orchid Key Inn - Adults Only + Flight

    Old Town Key West
    5 nights
    3.5 star property
    9.8/10 - Exceptional (1,006 reviews)
    "We LOVED our stay here. Small, boutique motel with a vintage feel. Right on Duvall, but you would never know it once in the motel. It was secluded and quiet with a lovely tropical feel. Loved the grounds - beautiful flowers, palms, gorgeous pool at night with candles around the tables. The staff was so helpful and friendly. Breakfast buffet is pretty good, but the areas around the pool were my favorite to sit & relax with a glass of wine from the bar. Our room was clean & comfortable. Lots of..."
    Reviewed November 8, 2026
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - EYW • Nonstop EYW - BOS • 1 stop
    $3,184
    $2,127
    per traveler
    found 1 day ago
    Orchid Key Inn - Adults Only
  • Dec 23 - Dec 28

    The Gardens Hotel + Flight

    Old Town Key West
    5 nights
    4.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West"
    Reviewed November 8, 2026
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - EYW • Nonstop EYW - BOS • 1 stop
    $3,466
    $2,434
    per traveler
    found 1 day ago
    The Gardens Hotel
  • Dec 23 - Dec 28

    The Perry Hotel & Marina Key West + Flight

    Stock Island
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,315 reviews)
    "Absolutely gorgeous room and property!! The price could not be beat this is definitely a hidden gem!!!"
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - EYW • Nonstop EYW - BOS • 1 stop
    $1,925
    $1,395
    per traveler
    found 1 day ago
    The Perry Hotel & Marina Key West

Top Cheap Key Haven Hotels

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.

Find amazing cheap vacations in Key Haven

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 $895, 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.