Cheap Vacations in Key West

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Key West vacations

Key West Marriott Beachside Hotel

Key West Marriott Beachside Hotel

3.5 out of 5
Price was $984, price is now $741 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Price was $1,228, price is now $1,005 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Eden House

Eden House

3.5 out of 5
Key West Historic District
Price was $1,164, price is now $979 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Key West Historic District
Price was $1,418, price is now $1,204 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Old Town Key West
Price was $2,349, price is now $2,000 per person
per person
Nov 17 - Nov 20
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Island City House Hotel

Island City House Hotel

3 out of 5
Key West Historic District
Save 100% on your flightPrice was $1,334, price is now $1,144 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
Key West Historic District
Price was $1,064, price is now $916 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Custom House by Brightwild

Custom House by Brightwild

3.5 out of 5
Key West Historic District
Price was $2,239, price is now $1,947 per person
per person
Oct 28 - Nov 2
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
Shipyard Treasure by Avantstay Communal Pool Gated Community Great Location Week Long Stays

Shipyard Treasure by Avantstay Communal Pool Gated Community Great Location Week Long Stays

3 out of 5
Old Town Key West
Save 100% on your flightPrice was $3,380, price is now $2,942 per person
per person
Nov 11 - Nov 18
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
Key West Historic District
Price was $1,100, price is now $965 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Prices and availability subject to change. Additional terms may apply.

3-night Key West vacations

Key West Marriott Beachside Hotel

Key West Marriott Beachside Hotel

3.5 out of 5
Price was $984, price is now $741 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Price was $1,228, price is now $1,005 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Eden House

Eden House

3.5 out of 5
Price was $1,164, price is now $979 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Price was $1,418, price is now $1,204 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Price was $2,349, price is now $2,000 per person
per person
Nov 17 - Nov 20
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
Price was $1,064, price is now $916 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $975, price is now $871 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
Price was $906, price is now $813 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
Price was $1,449, price is now $1,315 per person
per person
Nov 17 - Nov 20
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
Price was $1,451, price is now $1,330 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
H2O Suites - Adults Only

H2O Suites - Adults Only

3.5 out of 5
Price was $1,846, price is now $1,692 per person
per person
Nov 11 - Nov 14
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
Price was $1,201, price is now $1,102 per person
per person
Nov 17 - Nov 20
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Prices and availability subject to change. Additional terms may apply.

4-night Key West vacations

Key West Marriott Beachside Hotel

Key West Marriott Beachside Hotel

3.5 out of 5
Price was $1,442, price is now $1,078 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Price was $1,800, price is now $1,456 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Price was $4,418, price is now $3,978 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $1,490, price is now $1,349 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Grand Maloney Hotel

Grand Maloney Hotel

2 out of 5
Price was $2,488, price is now $2,274 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $1,312, price is now $1,215 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $1,535, price is now $1,437 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
Price was $1,271, price is now $1,221 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
Price was $1,251, price is now $1,216 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

3 out of 5
Price was $1,737, price is now $1,712 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

3 out of 5
Price was $1,779, price is now $1,755 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Papaya Place by Avantstay Great Location w/ Balcony, Outdoor Dining, Shared Pool & Hot Tub!

Papaya Place by Avantstay Great Location w/ Balcony, Outdoor Dining, Shared Pool & Hot Tub!

3 out of 5
Price was $1,777, price is now $1,753 per person
per person
Nov 10 - Nov 14
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
Prices and availability subject to change. Additional terms may apply.

5-night Key West vacations

Key West Marriott Beachside Hotel

Key West Marriott Beachside Hotel

3.5 out of 5
Save 100% on your flightPrice was $1,010, price is now $690 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Save 100% on your flightPrice was $1,545, price is now $1,176 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Eden House

Eden House

3.5 out of 5
Save 100% on your flightPrice was $1,103, price is now $900 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Save 100% on your flightPrice was $1,521, price is now $1,244 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Save 100% on your flightPrice was $1,545, price is now $1,269 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $876, price is now $725 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Save 100% on your flightPrice was $1,089, price is now $906 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
Price was $859, price is now $728 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Galleria by Brightwild

The Galleria by Brightwild

3 out of 5
Price was $1,103, price is now $936 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Island City House Hotel

Island City House Hotel

3 out of 5
Save 100% on your flightPrice was $1,334, price is now $1,144 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
Price was $816, price is now $709 per person
per person
Oct 30 - Nov 4
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Custom House by Brightwild

Custom House by Brightwild

3.5 out of 5
Price was $2,239, price is now $1,947 per person
per person
Oct 28 - Nov 2
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
Prices and availability subject to change. Additional terms may apply.

6-7 night Key West vacations

Key West Marriott Beachside Hotel

Key West Marriott Beachside Hotel

3.5 out of 5
Save 100% on your flightPrice was $1,748, price is now $1,196 per person
per person
Nov 11 - Nov 18
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Save 100% on your flightPrice was $2,619, price is now $2,097 per person
per person
Nov 11 - Nov 18
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
Price was $1,528, price is now $1,240 per person
per person
Nov 11 - Nov 18
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Save 100% on your flightPrice was $5,553, price is now $4,645 per person
per person
Nov 11 - Nov 18
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5