Cheap Vacations in Sunset Key

Choose two or more items and save on your trip:

Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was $1,311, price is now $960 per person
$960
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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
Old Town Key West
Save 100% on your flight
Price was $1,941, price is now $1,233 per person
$1,233
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,510, price is now $1,050 per person
$1,050
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $2,084, price is now $1,451 per person
$1,451
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,690, price is now $1,187 per person
$1,187
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,606, price is now $1,157 per person
$1,157
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,606, price is now $1,157 per person
$1,157
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $2,210, price is now $1,610 per person
$1,610
per person
Jun 11 - Jun 15
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Key West (EYW)
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,450, price is now $1,062 per person
$1,062
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,812, price is now $1,352 per person
$1,352
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)

3-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
Price was $742, price is now $579 per person
$579
per person
May 20 - May 23
found 13 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,777, price is now $1,208 per person
$1,208
per person
May 20 - May 23
found 13 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,216, price is now $859 per person
$859
per person
May 20 - May 23
found 13 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,107, price is now $796 per person
$796
per person
May 20 - May 23
found 13 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,001, price is now $735 per person
$735
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Price was $1,202, price is now $884 per person
$884
per person
May 20 - May 23
found 13 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $1,044, price is now $779 per person
$779
per person
May 20 - May 23
found 13 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,267, price is now $958 per person
$958
per person
Jun 10 - Jun 13
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $850, price is now $650 per person
$650
per person
May 20 - May 23
found 13 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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
Save 100% on your flight
Price was $2,135, price is now $1,638 per person
$1,638
per person
May 20 - May 23
found 13 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

3 out of 5
Price was $1,678, price is now $1,301 per person
$1,301
per person
Jun 10 - Jun 13
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $1,051, price is now $823 per person
$823
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)

4-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
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 $1,514, price is now $1,005 per person
$1,005
per person
Jun 14 - Jun 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Price was $3,096, price is now $2,245 per person
$2,245
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $2,210, price is now $1,610 per person
$1,610
per person
Jun 11 - Jun 15
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $1,538, price is now $1,166 per person
$1,166
per person
May 27 - May 31
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

3 out of 5
Price was $3,215, price is now $2,496 per person
$2,496
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $3,079, price is now $2,402 per person
$2,402
per person
Jun 11 - Jun 15
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Key West (EYW)
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 out of 5
Price was $3,172, price is now $2,497 per person
$2,497
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $1,415, price is now $1,116 per person
$1,116
per person
Jun 14 - Jun 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $3,625, price is now $2,868 per person
$2,868
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Sky Loft by Brightwild Penthouse in Prime Spot

Sky Loft by Brightwild Penthouse in Prime Spot

2 out of 5
Save 100% on your flight
Price was $1,683, price is now $1,353 per person
$1,353
per person
Jun 11 - Jun 15
found 3 hours ago
Roundtrip flight included
Orlando (MCO) 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 $1,713, price is now $1,378 per person
$1,378
per person
May 27 - May 31
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Sky Suites Retreat by Brightwild 2 Stunning Condos

Sky Suites Retreat by Brightwild 2 Stunning Condos

2 out of 5
Save 100% on your flight
Price was $5,390, price is now $4,340 per person
$4,340
per person
May 26 - May 30
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)

5-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
Save 100% on your flight
Price was $1,380, price is now $949 per person
$949
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $2,369, price is now $1,419 per person
$1,419
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,993, price is now $1,234 per person
$1,234
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Save 100% on your flight
Price was $2,130, price is now $1,345 per person
$1,345
per person
May 31 - Jun 5
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,941, price is now $1,233 per person
$1,233
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,489, price is now $1,034 per person
$1,034
per person
Jun 10 - Jun 15
found 9 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 $1,510, price is now $1,050 per person
$1,050
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,690, price is now $1,187 per person
$1,187
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 flight
Price was $1,606, price is now $1,157 per person
$1,157
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,606, price is now $1,157 per person
$1,157
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Save 100% on your flight
Price was $1,711, price is now $1,238 per person
$1,238
per person
May 31 - Jun 5
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Price was $1,311, price is now $960 per person
$960
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)

6-7 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
Save 100% on your flight
Price was $1,638, price is now $1,139 per person
$1,139
per person
May 29 - Jun 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $3,204, price is now $1,975 per person
$1,975
per person
Jun 8 - Jun 14
found 6 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $2,594, price is now $1,622 per person
$1,622
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,895, price is now $1,255 per person
$1,255
per person
Jun 10 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 $2,599, price is now $1,723 per person
$1,723
per person
Jun 8 - Jun 14
found 6 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,977, price is now $1,375 per person
$1,375
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Save 100% on your flight
Price was $2,084, price is now $1,451 per person
$1,451
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 flight
Price was $2,120, price is now $1,531 per person
$1,531
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $2,120, price is now $1,531 per person
$1,531
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $2,233, price is now $1,614 per person
$1,614
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,883, price is now $1,367 per person
$1,367
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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
Price was $3,325, price is now $2,430 per person
$2,430
per person
Jun 7 - Jun 14
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

Wed, Jun 10 - Tue, Jun 16
TPA
Tampa
EYW
Key West
$89 Roundtrip, found 2 days ago
$89
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Jun 10 from Tampa to Key West, returning Tue, Jun 16, priced at $89 found 2 days ago
Sat, May 9 - Wed, May 13
EWR
New York
EYW
Key West
$296 Roundtrip, found 16 hours ago
$296
Roundtrip
found 16 hours ago
Select United flight, departing Sat, May 9 from New York to Key West, returning Wed, May 13, priced at $296 found 16 hours ago
Mon, Dec 14 - Fri, Dec 18
BOS
Boston
EYW
Key West
$297 Roundtrip, found 2 days ago
$297
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Dec 14 from Boston to Key West, returning Fri, Dec 18, priced at $297 found 2 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
$226 nightly
The price is $254 total per night
$254 total
Apr 20 - Apr 21
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
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
1.44 mi from Sunset Key
$330 nightly
The price is $372 total per night
$372 total
May 19 - May 20
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
Free Cancellation
Reserve now, pay when you stay
2.68 mi from Sunset Key
$283 nightly
The price is $319 total per night
$319 total
May 18 - May 19
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
Don't see what you're looking for?
See all available properties in Sunset Key
View all properties
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.