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 $703, price is now $454 per person
$454
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 WiFi. Self parking, concierge services, and barbecue grills are also on offer.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,597, price is now $1,665 per person
$1,665
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Key West (EYW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like cooked-to-order breakfast and WiFi in public areas. Self parking, a terrace, and a picnic area are also offered.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was $1,967, price is now $1,428 per person
$1,428
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) 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.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,422, price is now $2,486 per person
$2,486
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,147, price is now $2,306 per person
$2,306
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas and barbecue grills.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was $2,500, price is now $1,893 per person
$1,893
per person
Jul 14 - Jul 19
found 18 hours ago
Roundtrip flight included
Dallas (DAL) 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 $454 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
$267 nightly
The price is $300 total per night
$300 total
Jun 22 - Jun 23
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
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$261 nightly
The price is $294 total per night
$294 total
Jun 29 - Jun 30
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 on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pool
Spa
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$295 nightly
The price is $332 total per night
$332 total
Jun 28 - Jun 29
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.
Pool
Spa
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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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