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Jackson Square Vacation Packages

Jackson Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Beachcomber Resort & Club

Beachcomber Resort & Club

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this beach resort in Pompano Beach. Enjoy 2 outdoor pools, a private beach, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Fort Lauderdale Beach and Pompano Beach are located nearby.
Mayfair House Hotel & Garden

Mayfair House Hotel & Garden

4.5 out of 5
per person
Jul 1 - Jul 5
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this boutique hotel in Miami. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Brickell City Centre and Bayside Marketplace are located nearby.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
per person
Jun 18 - Jun 23
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 5-star luxury hotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
Ocean Villas of Deerfield

Ocean Villas of Deerfield

2.5 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 30
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this motel in Deerfield Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Deerfield Beach Pier and Pompano Beach are located nearby.
Hilton Fort Lauderdale Beach Resort

Hilton Fort Lauderdale Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this beach resort in Fort Lauderdale. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Las Olas Beach and Fort Lauderdale Beach are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
per person
Jun 21 - Jun 25
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Stay at this 5-star luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4-star beach hotel in Sunny Isles Beach. Enjoy a beach locale, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Aventura Mall and Gulfstream Park Racing and Casino are located nearby.
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 26 - Jun 30
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 3.5-star hotel in Miami Beach. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.
B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this beach resort in Fort Lauderdale. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Las Olas Beach and Port Everglades are located nearby.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
per person
Jun 26 - Jun 30
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free breakfast, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Hilton Garden Inn Miami South Beach

Hilton Garden Inn Miami South Beach

3 out of 5
Save 100% on your flight
per person
Jun 18 - Jun 23
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 3-star beach hotel in Miami Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fontainebleau and Miami Beach Boardwalk are located nearby.
Kimpton EPIC Hotel, an IHG Hotel

Kimpton EPIC Hotel, an IHG Hotel

5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 5-star luxury hotel in Miami. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Brickell City Centre and Bayside Marketplace are located nearby.

3-4 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
Mayfair House Hotel & Garden

Mayfair House Hotel & Garden

4.5 out of 5
Coconut Grove
per person
Jul 1 - Jul 5
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Jul 1 - Jul 5
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Jul 11 - Jul 14
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jul 4 - Jul 7
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)

5-7 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
Ocean Villas of Deerfield

Ocean Villas of Deerfield

2.5 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 30
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Mayfair House Hotel & Garden

Mayfair House Hotel & Garden

4.5 out of 5
Coconut Grove
per person
Jul 8 - Jul 15
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Jun 18 - Jun 23
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Broadmore Miami Beach

Broadmore Miami Beach

3.5 out of 5
North Beach
Save 100% on your flight
per person
Jul 3 - Jul 10
Roundtrip flight included
New York (LGA) to Miami (MIA)

Jackson Square Last Minute Hotel Deals

NYAH Key West - Adults Only
NYAH Key West - Adults Only
3 out of 5
420 Margaret Street, Key West, FL
Stay at this 3-star guesthouse in Key West. Enjoy free breakfast, 3 outdoor pools, and a rooftop terrace. Our guests praise the pool and the helpful staff in ...
NYAH Key West - Adults Only
La Concha Key West
La Concha Key West
4 out of 5
430 Duval St, Key West, FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the ...
La Concha Key West
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and a beach locale. Our guests praise the pool and the bar in our reviews. ...
Southernmost Beach Resort
Heron House - Adult Only
Heron House - Adult Only
3.5 out of 5
512 Simonton St, Key West, FL
Stay at this B&B in Key West. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Heron House - Adult Only
Opal Key Resort & Marina, Key West
Opal Key Resort & Marina, Key West
4 out of 5
245 Front Street, Key West, FL
Stay at this 4-star hotel in Key West. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our ...
Opal Key Resort & Marina, Key West
Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns
4 out of 5
725 Truman Avenue, Key West, FL
Stay at this 4-star hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the bar and the helpful staff in our reviews. ...
Winslow's Bungalows - Key West Historic Inns
Amsterdam's Curry Mansion Inn
Amsterdam's Curry Mansion Inn
3 out of 5
511 Caroline St, Key West, FL
Book a stay at this historic B&B in Key West. Enjoy free WiFi, free parking, and private pools. Our guests praise the helpful staff and the convenient parking ...
Amsterdam's Curry Mansion Inn
Pier House Resort & Spa
Pier House Resort & Spa
4 out of 5
1 Duval St, Key West, FL
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
Pier House Resort & Spa
See all 2,601 properties in Jackson Square
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.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Jun 4 - Wed, Jun 12
ORD
O'Hare Intl.
MIA
Miami Intl.
$41 Roundtrip, found 2 hours ago
$41
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Jun 4 from O'Hare Intl. to Miami Intl., returning Wed, Jun 12, priced at $41 found 2 hours ago
Spirit Airlines
Wed, May 29 - Tue, Jun 4
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$41 Roundtrip, found 2 hours ago
$41
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, May 29 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Tue, Jun 4, priced at $41 found 2 hours ago
Frontier Airlines
Tue, Jun 4 - Wed, Jun 5
PHL
Philadelphia Intl.
MIA
Miami Intl.
$50 Roundtrip, just found
$50
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jun 4 from Philadelphia Intl. to Miami Intl., returning Wed, Jun 5, priced at $50 just found
Spirit Airlines
Tue, Jun 11 - Wed, Jun 12
LGA
LaGuardia
MIA
Miami Intl.
$53 Roundtrip, found 9 hours ago
$53
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Tue, Jun 11 from LaGuardia to Miami Intl., returning Wed, Jun 12, priced at $53 found 9 hours ago

Book the perfect getaway to Jackson Square

With Hotwire, booking your next trip to Key West Historic District is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Jackson Square while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Jackson Square flight and hotel package for as low as $302.

Living it up in Key West Historic District means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Jackson Square, Key West Historic District vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Jackson Square for some of the best accommodations and flight deals.

FAQs about cheap Jackson Square packages:

How to get cheap vacation deals to Jackson Square?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $125.

How much are Jackson Square packages?

Vacation packages to Jackson Square vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $302.

How to find cheap car rentals near Jackson Square?

Hotwire partners with some of the most reliable car rental companies in Key West Historic District to bring you the best car rental deals in Jackson Square for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Jackson Square now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Jackson Square right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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