Cheap Vacations in Sunset Key

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Sunset Key vacations

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 $1,786, price is now $1,128 per person
$1,128
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $5,565, price is now $3,110 per person
$3,110
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,553, price is now $1,711 per person
$1,711
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
Price was $2,633, price is now $1,765 per person
$1,765
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,857, price is now $1,941 per person
$1,941
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,407, price is now $1,654 per person
$1,654
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
Save 100% on your flight
Price was $1,869, price is now $1,288 per person
$1,288
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,149, price is now $2,188 per person
$2,188
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
New Town
Save 100% on your flight
Price was $1,878, price is now $1,311 per person
$1,311
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $1,811, price is now $1,281 per person
$1,281
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)

3-night Sunset Key vacations

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 $1,138, price is now $853 per person
$853
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $3,854, price is now $2,800 per person
$2,800
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $2,146, price is now $1,597 per person
$1,597
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $2,258, price is now $1,697 per person
$1,697
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was $1,180, price is now $917 per person
$917
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $1,647, price is now $1,282 per person
$1,282
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Price was $1,486, price is now $1,193 per person
$1,193
per person
Apr 22 - Apr 25
found 8 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Price was $1,436, price is now $1,153 per person
$1,153
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Price was $1,677, price is now $1,360 per person
$1,360
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $2,050, price is now $1,669 per person
$1,669
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $1,809, price is now $1,476 per person
$1,476
per person
Apr 22 - Apr 25
found 8 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Price was $1,661, price is now $1,355 per person
$1,355
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)

4-night Sunset Key vacations

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
Save 100% on your flight
Price was $1,264, price is now $892 per person
$892
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $2,776, price is now $1,972 per person
$1,972
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Save 100% on your flight
Price was $1,907, price is now $1,365 per person
$1,365
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was $1,497, price is now $1,147 per person
$1,147
per person
Apr 27 - May 1
found 18 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was $1,554, price is now $1,213 per person
$1,213
per person
Apr 27 - May 1
found 18 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
Price was $1,499, price is now $1,188 per person
$1,188
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Save 100% on your flight
Price was $2,107, price is now $1,677 per person
$1,677
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Save 100% on your flight
Price was $2,409, price is now $1,921 per person
$1,921
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,108, price is now $1,690 per person
$1,690
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Save 100% on your flight
Price was $1,904, price is now $1,527 per person
$1,527
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Save 100% on your flight
Price was $1,828, price is now $1,470 per person
$1,470
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
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
Price was $2,278, price is now $1,854 per person
$1,854
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)

5-night Sunset Key vacations

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 $1,786, price is now $1,128 per person
$1,128
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $5,565, price is now $3,110 per person
$3,110
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Save 100% on your flight
Price was $2,553, price is now $1,711 per person
$1,711
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,857, price is now $1,941 per person
$1,941
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Save 100% on your flight
Price was $1,869, price is now $1,288 per person
$1,288
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Save 100% on your flight
Price was $1,878, price is now $1,311 per person
$1,311
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $1,811, price is now $1,281 per person
$1,281
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,846, price is now $1,310 per person
$1,310
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Save 100% on your flight
Price was $2,145, price is now $1,538 per person
$1,538
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
Save 100% on your flight
Price was $1,953, price is now $1,418 per person
$1,418
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Eden House

Eden House

4 out of 5
Save 100% on your flight
Price was $1,815, price is now $1,328 per person
$1,328
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
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 $2,573, price is now $1,892 per person
$1,892
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)

6-7 night Sunset Key vacations

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
Save 100% on your flight
Price was $1,742, price is now $1,155 per person
$1,155
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $4,163, price is now $2,394 per person
$2,394
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Save 100% on your flight
Price was $3,016, price is now $1,995 per person
$1,995
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $2,633, price is now $1,765 per person
$1,765
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Save 100% on your flight
Price was $2,167, price is now $1,461 per person
$1,461
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,472, price is now $1,696 per person
$1,696
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Save 100% on your flight
Price was $2,407, price is now $1,654 per person
$1,654
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $2,259, price is now $1,559 per person
$1,559
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Save 100% on your flight
Price was $3,149, price is now $2,188 per person
$2,188
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Save 100% on your flight
Price was $3,458, price is now $2,435 per person
$2,435
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
Save 100% on your flight
Price was $2,517, price is now $1,788 per person
$1,788
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $3,108, price is now $2,223 per person
$2,223
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)

Flight deals to Sunset Key

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

Mon, Apr 13 - Fri, Apr 17
TPA
Tampa
EYW
Key West
$87 Roundtrip, found 3 days ago
$87
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Apr 13 from Tampa to Key West, returning Fri, Apr 17, priced at $87 found 3 days ago
Sun, Apr 5 - Wed, Apr 8
ATL
Atlanta
EYW
Key West
$217 Roundtrip, found 14 hours ago
$217
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Sun, Apr 5 from Atlanta to Key West, returning Wed, Apr 8, priced at $217 found 14 hours ago
Sun, Mar 29 - Thu, Apr 2
BOS
Boston
EYW
Key West
$250 Roundtrip, found 2 days ago
$250
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Mar 29 from Boston to Key West, returning Thu, Apr 2, priced at $250 found 2 days ago

Top rated hotels for your Sunset Key vacation

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
1.44 mi from Sunset Key
$501 nightly
The price is $563 total per night
$563 total
Apr 5 - Apr 6
Total with taxes and fees
With a stay at Southernmost Beach Resort and Guesthouses, you'll be centrally located in Key West, steps from South Beach and within a 5-minute walk of Southernmost Point.
Pool
Spa
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
2.68 mi from Sunset Key
$483 nightly
The price is $544 total per night
$544 total
Mar 25 - Mar 26
Total with taxes and fees
Located in Key West, Margaritaville Beach House Key West is by the ocean, a 4-minute drive from Fort East Martello Museum and Gallery and 6 minutes from Smathers Beach.
Pool
Pet friendly
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
2.83 mi from Sunset Key
$422 nightly
The price is $475 total per night
$475 total
Mar 8 - Mar 9
Total with taxes and fees
With a stay at Ibis Bay Beach Resort in Key West (Northside Resort), you'll be a 4-minute drive from Florida Keys Beaches and 5 minutes from Duval Street.
Don't see what you're looking for?
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.