Cheap Vacations in Sunset Key

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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
New Town
Price was $1,439, price is now $1,142 per person
$1,142
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $4,607, price is now $3,217 per person
$3,217
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,205, price is now $1,633 per person
$1,633
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,395, price is now $1,817 per person
$1,817
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Price was $3,151, price is now $2,407 per person
$2,407
per person
Apr 20 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock

2 out of 5
Price was $10,887, price is now $8,561 per person
$8,561
per person
Apr 20 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $3,500, price is now $2,755 per person
$2,755
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Price was $1,623, price is now $1,282 per person
$1,282
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
Price was $1,604, price is now $1,272 per person
$1,272
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

3 out of 5
Price was $2,247, price is now $1,783 per person
$1,783
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,115, price is now $890 per person
$890
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $1,642, price is now $1,274 per person
$1,274
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Price was $2,902, price is now $2,258 per person
$2,258
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,399, price is now $1,117 per person
$1,117
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,418, price is now $1,135 per person
$1,135
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,597, price is now $1,280 per person
$1,280
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,421, price is now $1,151 per person
$1,151
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $2,227, price is now $1,820 per person
$1,820
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Price was $1,930, price is now $1,600 per person
$1,600
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,919, price is now $1,592 per person
$1,592
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Price was $2,576, price is now $2,158 per person
$2,158
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,327, price is now $1,967 per person
$1,967
per person
Apr 15 - Apr 18
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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
Price was $1,439, price is now $1,142 per person
$1,142
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $4,607, price is now $3,217 per person
$3,217
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,205, price is now $1,633 per person
$1,633
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,395, price is now $1,817 per person
$1,817
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $1,623, price is now $1,282 per person
$1,282
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $1,604, price is now $1,272 per person
$1,272
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,738, price is now $1,418 per person
$1,418
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,943, price is now $1,587 per person
$1,587
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $1,970, price is now $1,610 per person
$1,610
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Price was $1,913, price is now $1,569 per person
$1,569
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,234, price is now $1,851 per person
$1,851
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
Price was $1,499, price is now $1,243 per person
$1,243
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)

5-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 $1,857, price is now $1,294 per person
$1,294
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Save 100% on your flight
Price was $3,089, price is now $2,079 per person
$2,079
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $2,452, price is now $1,669 per person
$1,669
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $3,559, price is now $2,425 per person
$2,425
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $2,137, price is now $1,468 per person
$1,468
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $2,401, price is now $1,665 per person
$1,665
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
Price was $2,340, price is now $1,668 per person
$1,668
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,545, price is now $1,816 per person
$1,816
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,485, price is now $1,796 per person
$1,796
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,444, price is now $1,787 per person
$1,787
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
Price was $1,877, price is now $1,393 per person
$1,393
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub

2 out of 5
Save 100% on your flight
Price was $2,466, price is now $1,846 per person
$1,846
per person
Apr 9 - Apr 14
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,153, price is now $1,504 per person
$1,504
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $4,583, price is now $2,629 per person
$2,629
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,464, price is now $1,537 per person
$1,537
per person
Apr 25 - May 2
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $3,233, price is now $2,221 per person
$2,221
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,584, price is now $1,809 per person
$1,809
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,781, price is now $1,963 per person
$1,963
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $4,501, price is now $3,185 per person
$3,185
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,842, price is now $2,017 per person
$2,017
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $3,744, price is now $2,659 per person
$2,659
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,763, price is now $1,964 per person
$1,964
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $2,728, price is now $1,949 per person
$1,949
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Save 100% on your flight
Price was $3,634, price is now $2,621 per person
$2,621
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 21 hours ago
$217
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sun, Apr 5 from Atlanta to Key West, returning Wed, Apr 8, priced at $217 found 21 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.
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
$383 nightly
The price is $431 total per night
$431 total
Mar 8 - Mar 9
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 8 minutes from Duval Street.
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.
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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.