Exclusive Jackson Square Vacation Deals

Jackson Square vacation package 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
Save 100% on your flight
Price was $1,236, price is now $755 per person
$755
per person
Feb 26 - Mar 1
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.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was $4,989, price is now $2,710 per person
$2,710
per person
Feb 2 - Feb 9
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
Price was $5,626, price is now $3,141 per person
$3,141
per person
Feb 2 - Feb 9
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 Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,826, price is now $1,052 per person
$1,052
per person
Feb 1 - Feb 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.
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 $3,162, price is now $1,984 per person
$1,984
per person
Feb 2 - Feb 9
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.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $3,280, price is now $2,078 per person
$2,078
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.

Frequently asked questions

How much are vacation packages to Jackson Square?
If you like the sound of hassle-free planning and great savings, our $755 Jackson Square vacation package will be right up your alley. With your flights and hotels sorted, organizing your trip around this well-loved attraction has never been easier.
Where can I get the best vacation package deals for Jackson Square?
For the perfect Jackson Square package deal, no one compares to Travelocity. Select from 400 partner airlines and 1,000,000 properties worldwide to create your ultimate trip — simple as that.
Why should I book my Jackson Square vacation package via Travelocity?
Savings, support and a stress-free booking are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you can relax knowing you'll always get the best deal available.

Top Jackson Square hotel deals

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
$429 nightly
The price is $483 total per night
$483 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
Pool
Pet friendly
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane Key West FL
Free Cancellation
Reserve now, pay when you stay
$413 nightly
The price is $464 total per night
$464 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
This guesthouse features an outdoor pool and a hot tub. Enjoy the free continental breakfast each morning. Self parking, a terrace, and a garden are also offered.
Pool
Hot Tub
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
$231 nightly
The price is $260 total per night
$260 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This bed & breakfast features an outdoor pool and a rooftop terrace. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, luggage storage, and concierge services are also on offer.
Pool
Breakfast included
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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.

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