Cheap Vacations in Sunset Key

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Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was $954, price is now $714 per person
$714
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,310, price is now $1,768 per person
$1,768
per person
Jun 22 - Jun 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,760, price is now $1,238 per person
$1,238
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
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 $3,492, price is now $2,466 per person
$2,466
per person
Jun 26 - Jul 3
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,749, price is now $1,283 per person
$1,283
per person
Jun 22 - Jun 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,502, price is now $1,136 per person
$1,136
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

3 out of 5
Save 100% on your flight
Price was $3,481, price is now $2,649 per person
$2,649
per person
Jul 7 - Jul 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,721, price is now $1,312 per person
$1,312
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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
Old Town Key West
Price was $1,608, price is now $1,264 per person
$1,264
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence

2 out of 5
Save 100% on your flight
Price was $2,325, price is now $1,873 per person
$1,873
per person
Jun 23 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)

3-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
The Palms Hotel

The Palms Hotel

3 out of 5
Price was $821, price is now $678 per person
$678
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Price was $954, price is now $714 per person
$714
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $1,502, price is now $1,136 per person
$1,136
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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 $1,241, price is now $1,000 per person
$1,000
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $1,425, price is now $1,152 per person
$1,152
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Save 100% on your flight
Price was $2,903, price is now $2,356 per person
$2,356
per person
Jun 30 - Jul 3
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Save 100% on your flight
Price was $2,586, price is now $2,112 per person
$2,112
per person
Jun 30 - Jul 3
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $1,002, price is now $822 per person
$822
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $1,272, price is now $1,044 per person
$1,044
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Price was $1,269, price is now $1,048 per person
$1,048
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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
Save 100% on your flight
Price was $1,869, price is now $1,546 per person
$1,546
per person
Jun 19 - Jun 22
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,055, price is now $874 per person
$874
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)

4-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,155, price is now $933 per person
$933
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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
Save 100% on your flight
Price was $1,366, price is now $965 per person
$965
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Price was $1,315, price is now $976 per person
$976
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $1,877, price is now $1,405 per person
$1,405
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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 $1,687, price is now $1,268 per person
$1,268
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $1,530, price is now $1,173 per person
$1,173
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Price was $1,327, price is now $1,032 per person
$1,032
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $1,747, price is now $1,401 per person
$1,401
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Save 100% on your flight
Price was $2,920, price is now $2,374 per person
$2,374
per person
Jun 12 - Jun 16
found 8 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $1,450, price is now $1,183 per person
$1,183
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Save 100% on your flight
Price was $2,616, price is now $2,141 per person
$2,141
per person
Jun 12 - Jun 16
found 8 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 $1,362, price is now $1,118 per person
$1,118
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)

5-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Save 100% on your flight
Price was $1,292, price is now $891 per person
$891
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
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 $2,893, price is now $2,238 per person
$2,238
per person
Jun 25 - Jun 30
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
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
Price was $2,795, price is now $2,190 per person
$2,190
per person
Jun 25 - Jun 30
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Save 100% on your flight
Price was $2,413, price is now $1,191 per person
$1,191
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $2,136, price is now $1,383 per person
$1,383
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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
Save 100% on your flight
Price was $1,695, price is now $1,104 per person
$1,104
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Save 100% on your flight
Price was $2,047, price is now $1,351 per person
$1,351
per person
Jun 23 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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
Save 100% on your flight
Price was $1,649, price is now $1,159 per person
$1,159
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Save 100% on your flight
Price was $1,760, price is now $1,238 per person
$1,238
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,266, price is now $917 per person
$917
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $1,317, price is now $966 per person
$966
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $1,365, price is now $1,020 per person
$1,020
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)

6-7 night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
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 $1,525, price is now $1,065 per person
$1,065
per person
Jun 26 - Jul 3
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) 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
Save 100% on your flight
Price was $2,418, price is now $1,497 per person
$1,497
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $2,795, price is now $1,753 per person
$1,753
per person
Jun 26 - Jul 3
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) 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
Save 100% on your flight
Price was $2,503, price is now $1,581 per person
$1,581
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Save 100% on your flight
Price was $1,713, price is now $1,144 per person
$1,144
per person
Jun 26 - Jul 3
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) 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 $1,594, price is now $1,074 per person
$1,074
per person
Jun 26 - Jul 3
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Save 100% on your flight
Price was $5,669, price is now $3,947 per person
$3,947
per person
Jun 30 - Jul 7
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,772, price is now $1,247 per person
$1,247
per person
Jun 26 - Jul 3
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
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 $3,492, price is now $2,466 per person
$2,466
per person
Jun 26 - Jul 3
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) 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 $2,277, price is now $1,614 per person
$1,614
per person
Jun 30 - Jul 7
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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
Save 100% on your flight
Price was $3,655, price is now $2,592 per person
$2,592
per person
Jun 30 - Jul 7
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $2,396, price is now $1,714 per person
$1,714
per person
Jun 26 - Jul 3
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) 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, Aug 24 - Thu, Aug 27
TPA
Tampa
EYW
Key West
$87 Roundtrip, found 3 days ago
$87
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Aug 24 from Tampa to Key West, returning Thu, Aug 27, priced at $87 found 3 days ago
Mon, Jul 6 - Wed, Jul 15
EWR
New York
EYW
Key West
$296 Roundtrip, found 8 hours ago
$296
Roundtrip
found 8 hours ago
Select United flight, departing Mon, Jul 6 from New York to Key West, returning Wed, Jul 15, priced at $296 found 8 hours ago
Mon, Jun 1 - Sat, Jun 6
BOS
Boston
EYW
Key West
$314 Roundtrip, found 6 days ago
$314
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Jun 1 from Boston to Key West, returning Sat, Jun 6, priced at $314 found 6 days ago

Top rated hotels for your Sunset Key vacation

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
3.75 mi from Sunset Key
$202 nightly
The price is $227 total per night
$227 total
Jun 3 - Jun 4
Total with taxes and fees
A stay at Blue Flamingo Resort Key West places you in the heart of Key West, within a 10-minute drive of Stock Island Yacht Club & Marina and Key West Lighthouse and Keeper's Quarters Museum.
Pool
Hot Tub
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
$241 nightly
The price is $271 total per night
$271 total
Jun 8 - Jun 9
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
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
1.44 mi from Sunset Key
$283 nightly
The price is $319 total per night
$319 total
May 26 - May 27
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
Don't see what you're looking for?
See all available properties in Sunset Key
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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.

Top Picks

^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.