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 $1,185, price is now $716 per person
$716
per person
May 6 - May 9
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.
Springtide House by Brightwild Waterfront Pool

Springtide House by Brightwild Waterfront Pool

2 out of 5
Price was $11,617, price is now $8,330 per person
$8,330
per person
May 8 - May 15
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5
Save 100% on your flight
Price was $2,792, price is now $2,010 per person
$2,010
per person
May 6 - May 13
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.
Palmgale House in Key West

Palmgale House in Key West

2 out of 5
Save 100% on your flight
Price was $11,529, price is now $8,301 per person
$8,301
per person
May 16 - May 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.
Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House

2 out of 5
Save 100% on your flight
Price was $13,702, price is now $9,902 per person
$9,902
per person
May 24 - May 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

3 out of 5
Save 100% on your flight
Price was $3,223, price is now $2,363 per person
$2,363
per person
Apr 13 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.

Frequently asked questions

How much are vacation packages to Jackson Square?
If you like the sound of hassle-free planning and great savings, our $716 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
$501 nightly
The price is $563 total per night
$563 total
Apr 5 - Apr 6
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
$417 nightly
The price is $469 total per night
$469 total
Apr 5 - Apr 6
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
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
$392 nightly
The price is $442 total per night
$442 total
Mar 30 - Mar 31
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
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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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