Cheap Vacations in Sunset Key

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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 $1,582, price is now $1,295 per person
$1,295
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $2,856, price is now $2,012 per person
$2,012
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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
Old Town Key West
Price was $3,863, price is now $2,917 per person
$2,917
per person
Dec 12 - Dec 18
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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
Old Town Key West
Price was $3,713, price is now $2,821 per person
$2,821
per person
Dec 12 - Dec 18
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 $3,149, price is now $2,494 per person
$2,494
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

3 out of 5
Beachside
Save 100% on your flight
Price was $1,757, price is now $1,407 per person
$1,407
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip 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
Beachside
Save 100% on your flight
Price was $1,778, price is now $1,424 per person
$1,424
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip 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
Price was $1,828, price is now $1,482 per person
$1,482
per person
Nov 26 - Nov 30
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
Price was $1,727, price is now $1,402 per person
$1,402
per person
Nov 26 - Nov 30
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
Old Town Key West
Price was $1,995, price is now $1,634 per person
$1,634
per person
Nov 26 - Nov 30
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.
The Palms Hotel

The Palms Hotel

3 out of 5
Price was $906, price is now $746 per person
$746
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Price was $1,494, price is now $1,114 per person
$1,114
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
Eden House

Eden House

4 out of 5
Save 100% on your flight
Price was $1,360, price is now $1,037 per person
$1,037
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $1,107, price is now $912 per person
$912
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
New Altair House by Brightwild Pool Pets

New Altair House by Brightwild Pool Pets

2 out of 5
Save 100% on your flight
Price was $5,323, price is now $4,389 per person
$4,389
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Price was $1,402, price is now $1,160 per person
$1,160
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $987, price is now $827 per person
$827
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Price was $1,062, price is now $893 per person
$893
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $892, price is now $754 per person
$754
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) 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 $1,764, price is now $1,496 per person
$1,496
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $986, price is now $842 per person
$842
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Price was $951, price is now $815 per person
$815
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)

4-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Price was $774, price is now $615 per person
$615
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $2,856, price is now $2,012 per person
$2,012
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

3 out of 5
Save 100% on your flight
Price was $1,757, price is now $1,407 per person
$1,407
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip 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 $1,778, price is now $1,424 per person
$1,424
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $1,828, price is now $1,482 per person
$1,482
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub

2 out of 5
Price was $1,695, price is now $1,376 per person
$1,376
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $1,727, price is now $1,402 per person
$1,402
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,582, price is now $1,295 per person
$1,295
per person
Nov 26 - Nov 30
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
Price was $1,995, price is now $1,634 per person
$1,634
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)
Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill

2 out of 5
Price was $1,855, price is now $1,521 per person
$1,521
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
Price was $1,559, price is now $1,282 per person
$1,282
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Price was $1,762, price is now $1,455 per person
$1,455
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Key West (EYW)

5-night Sunset Key vacations

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

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Price was $1,503, price is now $1,172 per person
$1,172
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $3,240, price is now $2,042 per person
$2,042
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $1,872, price is now $1,380 per person
$1,380
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $2,230, price is now $1,654 per person
$1,654
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $2,932, price is now $2,179 per person
$2,179
per person
Nov 29 - Dec 4
found 10 hours ago
Roundtrip flight included
Pittsburgh (PIT) 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
Save 100% on your flight
Price was $1,866, price is now $1,401 per person
$1,401
per person
Nov 29 - Dec 4
found 10 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Key West (EYW)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Price was $1,920, price is now $1,443 per person
$1,443
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

3 out of 5
Save 100% on your flight
Price was $2,483, price is now $1,914 per person
$1,914
per person
Dec 14 - Dec 19
found 17 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $2,348, price is now $1,824 per person
$1,824
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $2,018, price is now $1,568 per person
$1,568
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $2,251, price is now $1,766 per person
$1,766
per person
Dec 14 - Dec 19
found 17 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Price was $2,217, price is now $1,743 per person
$1,743
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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
Price was $1,453, price is now $1,108 per person
$1,108
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $3,662, price is now $2,338 per person
$2,338
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Save 100% on your flight
Price was $3,789, price is now $2,726 per person
$2,726
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $2,390, price is now $1,783 per person
$1,783
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $2,091, price is now $1,573 per person
$1,573
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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
Price was $3,863, price is now $2,917 per person
$2,917
per person
Dec 12 - Dec 18
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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
Price was $3,713, price is now $2,821 per person
$2,821
per person
Dec 12 - Dec 18
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

3 out of 5
Save 100% on your flight
Price was $3,352, price is now $2,548 per person
$2,548
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $2,179, price is now $1,662 per person
$1,662
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Eden House

Eden House

4 out of 5
Save 100% on your flight
Price was $2,583, price is now $1,982 per person
$1,982
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $3,067, price is now $2,369 per person
$2,369
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Caribbean House

Caribbean House

3 out of 5
Price was $1,644, price is now $1,273 per person
$1,273
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.

Sun, Jan 10 - Thu, Jan 14
PIE
St. Petersburg
EYW
Key West
$86 Roundtrip, found 12 hours ago
$86
Roundtrip
found 12 hours ago
Select Allegiant Air flight, departing Sun, Jan 10 from St. Petersburg to Key West, returning Thu, Jan 14, priced at $86 found 12 hours ago
Mon, Nov 2 - Tue, Nov 3
TPA
Tampa
EYW
Key West
$105 Roundtrip, found 3 days ago
$105
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Nov 2 from Tampa to Key West, returning Tue, Nov 3, priced at $105 found 3 days ago
Tue, Mar 2 - Wed, Mar 3
BOS
Boston
EYW
Key West
$301 Roundtrip, found 23 hours ago
$301
Roundtrip
found 23 hours ago
Select Bargain Flight flight, departing Tue, Mar 2 from Boston to Key West, returning Wed, Mar 3, priced at $301 found 23 hours ago

Top rated hotels for your Sunset Key vacation

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
2.68 mi from Sunset Key
$275 nightly
The price is $310 total per night
$310 total
Oct 25 - Oct 26
Total with taxes and fees
Located in Key West, Margaritaville Beach House Key West is by the ocean, within a 5-minute drive of Smathers Beach and Fort East Martello Museum and Gallery.
Pool
Hot Tub
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
3.31 mi from Sunset Key
$236 nightly
The price is $265 total per night
$265 total
Oct 30 - Oct 31
Total with taxes and fees
With a stay at Havana Cabana at Key West in Key West (New Town), you'll be a 5-minute drive from Florida Keys Beaches and 6 minutes from Duval Street.
Pool
Hot Tub
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
$166 nightly
The price is $187 total per night
$187 total
Oct 25 - Oct 26
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
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.