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Jackson Square Vacation Packages

Jackson Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
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 $2,170, price is now $1,732 per person
$1,732
per person
Mar 1 - Mar 5
found 4 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Key West (EYW)
Stay at this cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Smathers Beach are located nearby.
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 $3,852, price is now $2,646 per person
$2,646
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $5,208, price is now $3,582 per person
$3,582
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
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 $2,614, price is now $1,983 per person
$1,983
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

3 out of 5
Save 100% on your flight
Price was $7,043, price is now $5,346 per person
$5,346
per person
Mar 13 - Mar 20
found 7 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $3,782, price is now $2,875 per person
$2,875
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this beach hotel in Key West. 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 Duval Street and Southernmost Point are located nearby.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

3 out of 5
Save 100% on your flight
Price was $3,025, price is now $2,346 per person
$2,346
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Key West (EYW)
Stay at this cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $2,722, price is now $2,116 per person
$2,116
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $3,235, price is now $2,524 per person
$2,524
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $3,612, price is now $2,853 per person
$2,853
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Price was $4,618, price is now $3,649 per person
$3,649
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
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 helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
Price was $4,334, price is now $3,450 per person
$3,450
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.

3-4 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
New Town
Price was $1,682, price is now $1,295 per person
$1,295
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,232, price is now $2,081 per person
$2,081
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
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 $2,043, price is now $1,432 per person
$1,432
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,902, price is now $1,367 per person
$1,367
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)

5-7 Night Vacations in Jackson Square

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 $2,614, price is now $1,983 per person
$1,983
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Key West (EYW)
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 $3,852, price is now $2,646 per person
$2,646
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $5,208, price is now $3,582 per person
$3,582
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $7,043, price is now $5,346 per person
$5,346
per person
Mar 13 - Mar 20
found 7 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)

Jackson Square Last Minute Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Southernmost Beach Resort and Guesthouses
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
La Concha Key West, Autograph Collection
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane Key West FL
Stay at this guesthouse in Key West. Enjoy free breakfast, parking (surcharge), and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. ...
The Cabana Inn Key West - Adults Only
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
Duval House
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 breakfast and the pool in our reviews. Popular attractions ...
Heron House - Adult Only
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
501 Southard Street Key West FL
Stay at this hotel in Key West. Enjoy free breakfast, free parking, and a rooftop terrace. Our guests praise the helpful staff and the property condition in ...
Pegasus International Hotel
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 helpful staff ...
Pier House Resort & Spa
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 hotel in Key West. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opal Key Resort & Marina, Key West
See all 2,743 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.