Cheap Vacations in Sunset Key

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Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
Key West Historic District
Price was $1,584, price is now $1,292 per person
$1,292
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $3,708, price is now $2,516 per person
$2,516
per person
Dec 4 - Dec 9
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
Old Town Key West
Save 100% on your flight
Price was $2,037, price is now $1,490 per person
$1,490
per person
Dec 4 - Dec 9
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
Key West Historic District
Save 100% on your flight
Price was $2,245, price is now $1,737 per person
$1,737
per person
Dec 4 - Dec 9
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 $1,791, price is now $1,407 per person
$1,407
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,735, price is now $2,155 per person
$2,155
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Save 100% on your flight
Price was $2,793, price is now $2,207 per person
$2,207
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,179, price is now $1,729 per person
$1,729
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Price was $2,340, price is now $1,917 per person
$1,917
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill

2 out of 5
Key West Historic District
Price was $1,838, price is now $1,511 per person
$1,511
per person
Dec 13 - Dec 17
found 21 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

3-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $813, price is now $642 per person
$642
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $1,655, price is now $1,163 per person
$1,163
per person
Nov 22 - Nov 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 $1,107, price is now $829 per person
$829
per person
Nov 22 - Nov 25
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
Price was $1,037, price is now $819 per person
$819
per person
Nov 22 - Nov 25
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
Price was $1,010, price is now $800 per person
$800
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Price was $1,098, price is now $894 per person
$894
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Caribbean House

Caribbean House

3 out of 5
Price was $814, price is now $667 per person
$667
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,031, price is now $1,672 per person
$1,672
per person
Nov 22 - Nov 25
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Independent Inn - Formerly Heron House Court

The Independent Inn - Formerly Heron House Court

3 out of 5
Price was $974, price is now $804 per person
$804
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay

2 out of 5
Price was $8,968, price is now $7,413 per person
$7,413
per person
Dec 18 - Dec 21
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $1,282, price is now $1,060 per person
$1,060
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Price was $1,503, price is now $1,243 per person
$1,243
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)

4-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 $994, price is now $811 per person
$811
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $2,319, price is now $1,582 per person
$1,582
per person
Nov 23 - Nov 27
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
Save 100% on your flight
Price was $1,388, price is now $1,022 per person
$1,022
per person
Nov 23 - Nov 27
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
Price was $1,318, price is now $1,027 per person
$1,027
per person
Nov 23 - Nov 27
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
Price was $1,274, price is now $997 per person
$997
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,735, price is now $2,155 per person
$2,155
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,793, price is now $2,207 per person
$2,207
per person
Dec 1 - Dec 5
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 $1,243, price is now $992 per person
$992
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Price was $1,187, price is now $952 per person
$952
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Price was $1,439, price is now $1,154 per person
$1,154
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip 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
Price was $1,790, price is now $1,463 per person
$1,463
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Palms Hotel

The Palms Hotel

3 out of 5
Price was $1,133, price is now $927 per person
$927
per person
Nov 23 - Nov 27
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.
The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Price was $1,347, price is now $1,067 per person
$1,067
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $3,708, price is now $2,516 per person
$2,516
per person
Dec 4 - Dec 9
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
Save 100% on your flight
Price was $2,037, price is now $1,490 per person
$1,490
per person
Dec 4 - Dec 9
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 $2,245, price is now $1,737 per person
$1,737
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $7,402, price is now $5,781 per person
$5,781
per person
Dec 3 - Dec 8
found 5 hours ago
Roundtrip flight included
New York (NYC) 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 $1,791, price is now $1,407 per person
$1,407
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Save 100% on your flight
Price was $2,179, price is now $1,729 per person
$1,729
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,648, price is now $2,107 per person
$2,107
per person
Dec 10 - Dec 15
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking

2 out of 5
Save 100% on your flight
Price was $3,294, price is now $2,661 per person
$2,661
per person
Nov 25 - Nov 30
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
Price was $1,842, price is now $1,502 per person
$1,502
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
Price was $1,584, price is now $1,292 per person
$1,292
per person
Dec 5 - Dec 10
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 $2,143, price is now $1,784 per person
$1,784
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip 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 $1,123, price is now $834 per person
$834
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $3,306, price is now $2,051 per person
$2,051
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $3,433, price is now $2,377 per person
$2,377
per person
Dec 12 - Dec 19
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,885, price is now $1,341 per person
$1,341
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Price was $3,638, price is now $2,609 per person
$2,609
per person
Dec 12 - Dec 19
found 24 hours 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
Save 100% on your flight
Price was $2,744, price is now $1,972 per person
$1,972
per person
Dec 1 - Dec 8
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 $1,880, price is now $1,366 per person
$1,366
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $4,361, price is now $3,171 per person
$3,171
per person
Dec 12 - Dec 19
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Caribbean House

Caribbean House

3 out of 5
Save 100% on your flight
Price was $1,442, price is now $1,059 per person
$1,059
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Price was $2,745, price is now $2,030 per person
$2,030
per person
Dec 12 - Dec 19
found 24 hours ago
Roundtrip non-stop 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 $1,286, price is now $958 per person
$958
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,903, price is now $2,174 per person
$2,174
per person
Dec 12 - Dec 19
found 24 hours ago
Roundtrip non-stop 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, Jan 11 - Thu, Jan 14
PIE
St. Petersburg
EYW
Key West
$86 Roundtrip, found 22 hours ago
$86
Roundtrip
found 22 hours ago
Select Allegiant Air flight, departing Mon, Jan 11 from St. Petersburg to Key West, returning Thu, Jan 14, priced at $86 found 22 hours ago
Mon, Nov 2 - Tue, Nov 3
TPA
Tampa
EYW
Key West
$105 Roundtrip, found 2 days ago
$105
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Nov 2 from Tampa to Key West, returning Tue, Nov 3, priced at $105 found 2 days ago
Tue, Mar 2 - Wed, Mar 3
BOS
Boston
EYW
Key West
$301 Roundtrip, found 3 hours ago
$301
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Tue, Mar 2 from Boston to Key West, returning Wed, Mar 3, priced at $301 found 3 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.