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 Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,012, price is now $610 per person
$610
per person
Jan 12 - Jan 15
found 1 day ago
Roundtrip 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.
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 $1,051, price is now $631 per person
$631
per person
Jan 12 - Jan 15
found 1 day ago
Roundtrip 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.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,034, price is now $1,267 per person
$1,267
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,506, price is now $2,261 per person
$2,261
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool, self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
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 $1,097, price is now $731 per person
$731
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip 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.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,067, price is now $1,381 per person
$1,381
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip 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.

Frequently asked questions

How much are vacation packages to Jackson Square?
If you like the sound of hassle-free planning and great savings, our $610 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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Free Cancellation
$242 nightly
The price is $272 total per night
$272 total
Nov 30 - Dec 1
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
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St, Key West, FL
$225 nightly
The price is $253 total per night
$253 total
Nov 30 - Dec 1
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
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$457 nightly
The price is $514 total per night
$514 total
Nov 23 - Nov 24
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.
On private beach
Pool
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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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