Key Haven Vacation Packages

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Top Key Haven Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $2,677, price is now CA $1,913 per person
CA $1,913
per person
May 17 - May 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,011 reviews)
Clean room, amazing outdoor pool

Reviewed on Apr 13, 2026

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was CA $3,499, price is now CA $2,373 per person
CA $2,373
per person
May 29 - Jun 4
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
Excellent villas, very clean and equipped with everything you need to make your stay memorable.

Reviewed on Apr 13, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $4,354, price is now CA $3,167 per person
CA $3,167
per person
Jul 2 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (542 reviews)
Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!

Reviewed on Apr 5, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Price was CA $4,669, price is now CA $3,452 per person
CA $3,452
per person
Jul 2 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (345 reviews)
Location was great. Near most of Key West Attractions. Parked the car and walked everywhere.

Reviewed on Apr 14, 2026

New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House

2 out of 5
Price was CA $23,401, price is now CA $17,683 per person
CA $17,683
per person
Jun 29 - Jul 6
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
No reviews

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Key Haven Hotel Deals

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from May 10 to May 11
CA $247
CA $355 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (2,086 reviews)
Travelled with small children. The site stated there was a hot tub, but we could not find the hot tub and the pool was cold, making it hard for my family to enjoy the pool when we couldn’t warm up in a hot tub. The live music was quite loud, with the bass traveling pretty much uninterrupted into ...

Reviewed on Apr 14, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $325 per night from May 10 to May 11
CA $325
CA $453 total
May 10 - May 11
includes taxes & fees
8.8/10 Excellent! (1,814 reviews)
We were not guaranteed ocean view rooms even though we booked that, but still ended up with a beautiful ocean view in the top floor. We had great access to Smathers Beach! Overall, I don’t think it was worth over $8k including plane tickets to go here for a week.

Reviewed on Apr 14, 2026

Margaritaville Beach House Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is CA $414 per night from May 12 to May 13
CA $414
CA $567 total
May 12 - May 13
includes taxes & fees
8.8/10 Excellent! (3,220 reviews)
The resort overall was amazing! Close proximity to the beach and Duval Street was so accessible. It would have been nice if the pool bars were open later in the evening. Our room was basic but clean. A full length mirror would have been great as well as a longer vanity in the bathroom. Not enough ...

Reviewed on Apr 14, 2026

Southernmost Beach Resort and Guesthouses
See all 3,140 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.
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Frequently asked questions

Can I cancel my flight booking to Key Haven due to COVID-19?
Our helpful Customer Service Portal is your one-stop shop for most travel queries, including about flight cancellations and changes due to COVID-19. For extra peace of mind, we suggest looking over the terms and conditions of your chosen airline before reserving your tickets.
What's the best way to find cheap flights to Key Haven that have flexible change policies?
Search for affordable airfares to Key Haven, then mark the "No change fee" box directly underneath the "Flexible change policies" subheading. It really is that simple. We get that plans can change and flexibility matters, so you can book with confidence with Expedia.
What are some of the general tips for travelers to Key Haven during the COVID-19 outbreak?
If it's your first time traveling during the COVID-19 outbreak, you'll notice a few more rules and restrictions in place. Take note of these tips and make your journey to Key Haven a smooth one:
  • Investigate if any travel restrictions apply to your origin and destination before booking. Also check if there are any conditions you'll need to follow on arrival, such as testing and quarantining.
  • Keep your face mask on during airport screening. A TSA officer will ask you to lower your mask temporarily for identification purposes.
  • To reduce the potential of cross-contamination, position your boarding pass on the scanner yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA agent.
  • You can now take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on baggage. This will need to be taken out for X-ray scanning.
  • To minimize handling during screening, place personal items such as your loose change and phone into your carry-on rather than into the bins.
  • Separate any food you're carrying for screening. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA agent to touch and inspect your belongings.

Which airlines fly to Key Haven?
Delta is a well-known airline servicing Key Haven. Lock in an airfare to Key West Intl. Airport (EYW) and you'll have 191 Delta flights every month to pick from.
How can I find cheap tickets to Key Haven?
Start searching as early as possible, consider nearby airports, use frequent flyer miles — there's no shortage of ways! One more is to make the most of Expedia's "flexible dates" function. Find your Key Haven flight, then check out the cheapest prices for nearby dates. In the last seven days, the best price for a flight to Key Haven was .
How much is a flight to Key Haven?
One-way flights departing from () sold for as low as in the last seven days. During this time, the cost of a return airfare to Key Haven varied between and . If you find a deal, grab it fast — these fares don't hang around.
What are the most popular airports to fly into in Key Haven?
Key West Intl. Airport (EYW) is the main entrance point for many hoping to visit Key Haven. Roughly 1119 flights each month land at this airport.
When is the cheapest time to fly to Key Haven?
Take off for Key Haven earlier in the week and you'll usually be rewarded with lower fares. Tuesday is generally the cheapest day to hop on a plane, closely followed by Monday. If you'd like to avoid the priciest flights, give Saturdays a wide berth.
How much is a plane ticket to Key Haven?
In the last seven days, tickets to Key Haven ranged from to .
Which airlines with flights to Key Haven employ COVID-19 cleanliness policies?
While traveling during a pandemic can be nerve-wracking, airlines are doing all they can to protect the well-being of all on board. These are a few carriers that have implemented changes:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.