Deals on vacations and trips to Key Haven

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Key Haven flight + hotel vacation packages

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

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,525, price is now $924 per person
$924
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit box and concierge services are also provided.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,457, price is now $1,427 per person
$1,427
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $3,043, price is now $1,840 per person
$1,840
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,544, price is now $934 per person
$934
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,498, price is now $998 per person
$998
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Top Key Haven hotels deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$311 nightly
The price is $350 total per night
$350 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.
On private beach
Pool
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$283 nightly
The price is $318 total per night
$318 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Pool
Hot Tub
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$291 nightly
The price is $327 total per night
$327 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Pool
Pet friendly
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$277 nightly
The price is $312 total per night
$312 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free beach shuttle.
Pool
Free airport shuttle
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
$293 nightly
The price is $329 total per night
$329 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
$345 nightly
The price is $389 total per night
$389 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Pool
Spa
Don't see what you're looking for?
See all available properties in Key Haven
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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.

Frequently asked questions

How much are vacation packages to Key Haven?
Your travel dreams can become a reality in Key Haven from an impressive $924. Our vacation packages include flights and hotels, so booking your trip will be a cinch. The only thing you'll need to focus on is having a good time.
Where can I get the best vacation package deals for Key Haven?
Travelocity has endless ways to score an amazing Key Haven package deal. Choose from 400 airlines and 1,000,000 properties around the globe and craft a vacation package that's suited to you. With so many options at hand, it's time to start planning your next big adventure.
Why should I purchase my Key Haven vacation bundle via Travelocity?
Nothing tops the satisfaction of knowing you've scored the best deal in town — that's our Price Match Guarantee. Add to that our fantastic range of magical destinations and 24/7 team of customer service professionals and you've got the blueprint for an unforgettable vacation.
Can I save on my Key Haven car rental if I bundle it with my hotel or flight?
You can with our Key Haven vacation packages. With one of these, there are lots of ways to make your hard-earned cash go further. Combine any two or more car, hotel, flight and tour bookings and see the savings pile up. With your own set of wheels, all the popular attractions around Key Haven are a fun road trip away.
Where should I stay when visiting Key Haven?
If you're looking for somewhere to base yourself, have a look at the Key Haven Oasis! 3 Bedroom Waterfront Home w/Pool. It's the top choice for many travelers.

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