Cheap Vacations in Sunset Key

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Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
Old Town Key West
Price was $1,008, price is now $797 per person
$797
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) 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
Price was $1,702, price is now $1,111 per person
$1,111
per person
Oct 5 - Oct 9
found 23 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $2,464, price is now $1,656 per person
$1,656
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) 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
Save 100% on your flight
Price was $4,314, price is now $3,221 per person
$3,221
per person
Oct 12 - Oct 19
just found
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive

3 out of 5
Old Town Key West
Price was $1,330, price is now $998 per person
$998
per person
Oct 5 - Oct 9
found 23 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Lighthouse Suites Collection

Lighthouse Suites Collection

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,739, price is now $1,307 per person
$1,307
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
Old Town Key West
Price was $1,225, price is now $931 per person
$931
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Old Town Key West
Price was $1,257, price is now $960 per person
$960
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) 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 $1,518, price is now $1,210 per person
$1,210
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was $1,315, price is now $1,050 per person
$1,050
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)

3-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
Price was $871, price is now $720 per person
$720
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $2,464, price is now $1,656 per person
$1,656
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Lighthouse Suites Collection

Lighthouse Suites Collection

4 out of 5
Save 100% on your flight
Price was $1,739, price is now $1,307 per person
$1,307
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
Price was $1,225, price is now $931 per person
$931
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Price was $1,257, price is now $960 per person
$960
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
Price was $1,008, price is now $797 per person
$797
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $1,518, price is now $1,210 per person
$1,210
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $1,315, price is now $1,050 per person
$1,050
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $982, price is now $790 per person
$790
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $1,153, price is now $944 per person
$944
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Price was $1,091, price is now $898 per person
$898
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
The Mermaid & Alligator

The Mermaid & Alligator

3.5 out of 5
Price was $1,137, price is now $936 per person
$936
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)

4-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
Price was $1,070, price is now $852 per person
$852
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) 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 $1,702, price is now $1,111 per person
$1,111
per person
Oct 5 - Oct 9
found 23 hours 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 $3,367, price is now $2,203 per person
$2,203
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
Save 100% on your flight
Price was $1,623, price is now $1,199 per person
$1,199
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive

3 out of 5
Price was $1,330, price is now $998 per person
$998
per person
Oct 5 - Oct 9
found 23 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $1,173, price is now $897 per person
$897
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
Price was $1,205, price is now $929 per person
$929
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Save 100% on your flight
Price was $1,862, price is now $1,443 per person
$1,443
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) 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 $2,089, price is now $1,627 per person
$1,627
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Lighthouse Suites Collection

Lighthouse Suites Collection

4 out of 5
Save 100% on your flight
Price was $2,306, price is now $1,816 per person
$1,816
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Price was $1,640, price is now $1,302 per person
$1,302
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Price was $1,479, price is now $1,178 per person
$1,178
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Key West (EYW)

5-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
Price was $1,281, price is now $964 per person
$964
per person
Oct 17 - Oct 22
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 $4,215, price is now $2,539 per person
$2,539
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
Save 100% on your flight
Price was $1,927, price is now $1,312 per person
$1,312
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 flight
Price was $2,492, price is now $1,707 per person
$1,707
per person
Oct 17 - Oct 22
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
Save 100% on your flight
Price was $2,247, price is now $1,613 per person
$1,613
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
Save 100% on your flight
Price was $1,655, price is now $1,190 per person
$1,190
per person
Oct 17 - Oct 22
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 $2,539, price is now $1,867 per person
$1,867
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,462, price is now $1,091 per person
$1,091
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $1,376, price is now $1,027 per person
$1,027
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Price was $1,732, price is now $1,301 per person
$1,301
per person
Oct 17 - Oct 22
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 $1,999, price is now $1,517 per person
$1,517
per person
Oct 17 - Oct 22
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
Save 100% on your flight
Price was $2,292, price is now $1,746 per person
$1,746
per person
Oct 17 - Oct 22
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 Porch on Frances Inn

The Porch on Frances Inn

4.5 out of 5
Price was $1,581, price is now $1,228 per person
$1,228
per person
Oct 12 - Oct 19
just found
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 $3,546, price is now $2,546 per person
$2,546
per person
Oct 5 - Oct 12
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 $4,314, price is now $3,221 per person
$3,221
per person
Oct 12 - Oct 19
just found
Roundtrip non-stop flight included
Detroit (DTW) 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 $3,521, price is now $2,659 per person
$2,659
per person
Oct 12 - Oct 19
just found
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
Price was $2,016, price is now $1,529 per person
$1,529
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,762, price is now $1,358 per person
$1,358
per person
Oct 5 - Oct 12
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
Save 100% on your flight
Price was $2,827, price is now $2,194 per person
$2,194
per person
Oct 12 - Oct 19
just found
Roundtrip non-stop flight included
Detroit (DTW) 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 $1,999, price is now $1,568 per person
$1,568
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Curry House

Curry House

2 out of 5
Price was $1,767, price is now $1,389 per person
$1,389
per person
Oct 12 - Oct 19
just found
Roundtrip non-stop flight included
Detroit (DTW) 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 $2,043, price is now $1,628 per person
$1,628
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Price was $2,632, price is now $2,101 per person
$2,101
per person
Oct 5 - Oct 12
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 $2,371, price is now $1,899 per person
$1,899
per person
Oct 5 - Oct 12
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.

Fri, Sep 25 - Wed, Sep 30
PIE
St. Petersburg
EYW
Key West
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Fri, Sep 25 from St. Petersburg to Key West, returning Wed, Sep 30, priced at $99 found 3 days ago
Sat, Sep 12 - Mon, Sep 14
TPA
Tampa
EYW
Key West
$133 Roundtrip, found 2 days ago
$133
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Sep 12 from Tampa to Key West, returning Mon, Sep 14, priced at $133 found 2 days ago
Fri, Feb 26 - Wed, Mar 3
EWR
New York
EYW
Key West
$319 Roundtrip, found 6 days ago
$319
Roundtrip
found 6 days ago
Select United flight, departing Fri, Feb 26 from New York to Key West, returning Wed, Mar 3, priced at $319 found 6 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
Reserve now, pay when you stay
1.44 mi from Sunset Key
$210 nightly
The price is $237 total per night
$237 total
Sep 13 - Sep 14
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
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
3.88 mi from Sunset Key
$195 nightly
The price is $219 total per night
$219 total
Sep 7 - Sep 8
Total with taxes and fees
When you stay at Beachside Resort & Residences in Key West, you'll be next to a golf course, a 5-minute drive from Smathers Beach and 6 minutes from Florida Keys Beaches.
On private beach
Pool
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
2.68 mi from Sunset Key
$234 nightly
The price is $263 total per night
$263 total
Sep 20 - Sep 21
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
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.