Cheap Vacations in Sunset Key

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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
Northside Resort
Price was $890, price is now $676 per person
$676
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip 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
Old Town Key West
Save 100% on your flight
Price was $1,762, price is now $1,467 per person
$1,467
per person
Sep 5 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 $1,557, price is now $1,064 per person
$1,064
per person
Aug 26 - Aug 30
found 19 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 $1,852, price is now $1,278 per person
$1,278
per person
Aug 26 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Price was $1,319, price is now $990 per person
$990
per person
Aug 26 - Aug 30
found 19 hours 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 $1,003, price is now $775 per person
$775
per person
Aug 26 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

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 $2,937, price is now $2,345 per person
$2,345
per person
Aug 18 - Aug 23
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 $3,007, price is now $2,402 per person
$2,402
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was $911, price is now $740 per person
$740
per person
Aug 26 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Northside Resort
Price was $867, price is now $705 per person
$705
per person
Aug 26 - Aug 30
found 19 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 $890, price is now $676 per person
$676
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $1,791, price is now $1,511 per person
$1,511
per person
Sep 5 - Sep 8
found 19 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Price was $1,449, price is now $1,069 per person
$1,069
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 $2,613, price is now $2,095 per person
$2,095
per person
Sep 4 - Sep 7
found 22 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Price was $1,017, price is now $828 per person
$828
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
Price was $877, price is now $716 per person
$716
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 $2,176, price is now $1,815 per person
$1,815
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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 $1,934, price is now $1,633 per person
$1,633
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
The Palms Hotel

The Palms Hotel

3 out of 5
Price was $836, price is now $707 per person
$707
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $806, price is now $686 per person
$686
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Price was $943, price is now $812 per person
$812
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
Price was $901, price is now $779 per person
$779
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)

4-night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Price was $867, price is now $705 per person
$705
per person
Aug 26 - Aug 30
found 19 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
Save 100% on your flight
Price was $1,762, price is now $1,467 per person
$1,467
per person
Sep 5 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Key West (EYW)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,557, price is now $1,064 per person
$1,064
per person
Aug 26 - Aug 30
found 19 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 $1,852, price is now $1,278 per person
$1,278
per person
Aug 26 - Aug 30
found 19 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 $1,006, price is now $711 per person
$711
per person
Aug 26 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Price was $1,319, price is now $990 per person
$990
per person
Aug 26 - Aug 30
found 19 hours 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 $1,003, price is now $775 per person
$775
per person
Aug 26 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $3,007, price is now $2,402 per person
$2,402
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $911, price is now $740 per person
$740
per person
Aug 26 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Palms Hotel

The Palms Hotel

3 out of 5
Price was $891, price is now $725 per person
$725
per person
Aug 26 - Aug 30
found 19 hours 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 $996, price is now $811 per person
$811
per person
Aug 26 - Aug 30
found 19 hours 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 $1,289, price is now $1,051 per person
$1,051
per person
Aug 26 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $695, price is now $574 per person
$574
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $2,099, price is now $1,710 per person
$1,710
per person
Sep 11 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) 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 $983, price is now $706 per person
$706
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Save 100% on your flight
Price was $2,937, price is now $2,345 per person
$2,345
per person
Aug 18 - Aug 23
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $1,288, price is now $1,065 per person
$1,065
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $1,194, price is now $989 per person
$989
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $2,016, price is now $1,670 per person
$1,670
per person
Aug 18 - Aug 23
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

3 out of 5
Price was $1,769, price is now $1,466 per person
$1,466
per person
Aug 18 - Aug 23
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Price was $1,411, price is now $1,171 per person
$1,171
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
Price was $1,364, price is now $1,148 per person
$1,148
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $1,328, price is now $1,139 per person
$1,139
per person
Sep 1 - Sep 6
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access

2 out of 5
Price was $1,469, price is now $1,260 per person
$1,260
per person
Sep 1 - Sep 6
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)

6-7 night Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Price was $1,358, price is now $1,131 per person
$1,131
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Price was $2,321, price is now $1,695 per person
$1,695
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $2,843, price is now $2,080 per person
$2,080
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $1,628, price is now $1,203 per person
$1,203
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Price was $1,737, price is now $1,358 per person
$1,358
per person
Aug 27 - Sep 3
found 20 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Caribbean House

Caribbean House

3 out of 5
Price was $1,570, price is now $1,237 per person
$1,237
per person
Aug 27 - Sep 3
found 20 hours ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
Price was $1,459, price is now $1,216 per person
$1,216
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $2,802, price is now $2,364 per person
$2,364
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,431, price is now $1,210 per person
$1,210
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $1,760, price is now $1,499 per person
$1,499
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $1,602, price is now $1,366 per person
$1,366
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $2,631, price is now $2,249 per person
$2,249
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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, Aug 23 - Tue, Aug 25
TPA
Tampa
EYW
Key West
$84 Roundtrip, found 4 days ago
$84
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, Aug 23 from Tampa to Key West, returning Tue, Aug 25, priced at $84 found 4 days ago
Sun, Aug 23 - Wed, Aug 26
PIE
St. Petersburg
EYW
Key West
$86 Roundtrip, found 6 days ago
$86
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Sun, Aug 23 from St. Petersburg to Key West, returning Wed, Aug 26, priced at $86 found 6 days ago
Sun, Dec 13 - Fri, Dec 18
BOS
Boston
EYW
Key West
$274 Roundtrip, found 6 days ago
$274
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Sun, Dec 13 from Boston to Key West, returning Fri, Dec 18, priced at $274 found 6 days ago

Top rated hotels for your Sunset Key vacation

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
$202 nightly
The price is $227 total per night
$227 total
Aug 18 - Aug 19
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.
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
Aug 18 - Aug 19
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.
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
3.84 mi from Sunset Key
$155 nightly
The price is $175 total per night
$175 total
Aug 16 - Aug 17
Total with taxes and fees
In the heart of Key West, Hilton Garden Inn Key West / The Keys Collection is within a 5-minute drive of Key West Tropical Forest and Botanical Garden and Key West Art and Historical Society.
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.