Cheap Vacations in Sunset Key

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Sunset Key vacations

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,468, price is now $1,103 per person
$1,103
per person
Apr 25 - Apr 29
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
Key West Historic District
Save 100% on your flight
Price was $3,997, price is now $2,876 per person
$2,876
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

3 out of 5
Save 100% on your flight
Price was $2,805, price is now $2,022 per person
$2,022
per person
Apr 10 - Apr 16
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
New Town
Price was $2,501, price is now $1,852 per person
$1,852
per person
Apr 16 - Apr 21
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
Price was $2,579, price is now $1,910 per person
$1,910
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip 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 $2,749, price is now $2,044 per person
$2,044
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Resort View 3BR Residence

Resort View 3BR Residence

2 out of 5
Price was $5,120, price is now $3,885 per person
$3,885
per person
Apr 20 - Apr 25
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 $2,387, price is now $1,819 per person
$1,819
per person
Apr 16 - Apr 21
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
Key West Historic District
Price was $2,969, price is now $2,264 per person
$2,264
per person
Apr 16 - Apr 21
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
Old Town Key West
Save 100% on your flight
Price was $2,640, price is now $2,029 per person
$2,029
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip non-stop 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 $1,123, 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)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $4,077, price is now $2,876 per person
$2,876
per person
Apr 8 - 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
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)
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 Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $2,227, price is now $1,821 per person
$1,821
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 $1,634, price is now $1,355 per person
$1,355
per person
Apr 23 - Apr 26
found 1 day 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
Price was $1,684, price is now $1,400 per person
$1,400
per person
Apr 8 - Apr 11
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
Price was $2,588, 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)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Price was $1,622, price is now $1,356 per person
$1,356
per person
Apr 8 - Apr 11
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
Price was $1,368, price is now $1,161 per person
$1,161
per person
Apr 30 - May 3
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 $1,336, price is now $1,140 per person
$1,140
per person
Apr 30 - May 3
found 1 day 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 $1,156, price is now $871 per person
$871
per person
Apr 25 - Apr 29
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 $2,330, price is now $1,677 per person
$1,677
per person
Apr 25 - Apr 29
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 $1,806, price is now $1,336 per person
$1,336
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip 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
Save 100% on your flight
Price was $1,468, price is now $1,103 per person
$1,103
per person
Apr 25 - Apr 29
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
Save 100% on your flight
Price was $1,692, price is now $1,302 per person
$1,302
per person
Apr 25 - Apr 29
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 $1,587, price is now $1,225 per person
$1,225
per person
Apr 25 - Apr 29
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
Save 100% on your flight
Price was $1,788, price is now $1,381 per person
$1,381
per person
Apr 25 - Apr 29
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
Save 100% on your flight
Price was $1,657, price is now $1,312 per person
$1,312
per person
Apr 25 - Apr 29
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 $1,473, price is now $1,197 per person
$1,197
per person
Apr 25 - Apr 29
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 $1,680, price is now $1,369 per person
$1,369
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,907, price is now $1,557 per person
$1,557
per person
Apr 23 - Apr 27
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 $1,727, price is now $1,418 per person
$1,418
per person
Apr 25 - Apr 29
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.
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 $2,051, price is now $1,558 per person
$1,558
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House

2 out of 5
Save 100% on your flight
Price was $16,606, price is now $13,145 per person
$13,145
per person
Apr 15 - Apr 20
found 24 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $3,997, price is now $2,876 per person
$2,876
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Save 100% on your flight
Price was $3,396, price is now $2,451 per person
$2,451
per person
Apr 6 - Apr 11
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 $2,501, price is now $1,852 per person
$1,852
per person
Apr 16 - Apr 21
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 $2,579, price is now $1,910 per person
$1,910
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip 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 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Resort View 3BR Residence

Resort View 3BR Residence

2 out of 5
Price was $5,120, price is now $3,885 per person
$3,885
per person
Apr 20 - Apr 25
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 $2,387, price is now $1,819 per person
$1,819
per person
Apr 16 - Apr 21
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
Price was $3,139, price is now $2,393 per person
$2,393
per person
Apr 20 - Apr 25
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 $2,969, price is now $2,264 per person
$2,264
per person
Apr 16 - Apr 21
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
Save 100% on your flight
Price was $2,640, price is now $2,029 per person
$2,029
per person
Apr 6 - Apr 11
found 1 day 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.
Eden House

Eden House

3.5 out of 5
Save 100% on your flight
Price was $1,672, price is now $1,346 per person
$1,346
per person
Apr 10 - Apr 16
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
Save 100% on your flight
Price was $2,644, price is now $1,682 per person
$1,682
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Save 100% on your flight
Price was $3,918, price is now $2,790 per person
$2,790
per person
Apr 6 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

3 out of 5
Save 100% on your flight
Price was $2,805, price is now $2,022 per person
$2,022
per person
Apr 10 - Apr 16
found 1 day 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 $2,588, price is now $1,880 per person
$1,880
per person
Apr 10 - Apr 17
found 1 day ago
Roundtrip 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 $2,749, price is now $2,044 per person
$2,044
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop 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
Save 100% on your flight
Price was $2,951, price is now $2,216 per person
$2,216
per person
Apr 6 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Coconut Beach Resort Timeshare

Coconut Beach Resort Timeshare

2 out of 5
Save 100% on your flight
Price was $5,939, price is now $4,594 per person
$4,594
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill

2 out of 5
Save 100% on your flight
Price was $3,358, price is now $2,627 per person
$2,627
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
Save 100% on your flight
Price was $2,707, price is now $2,128 per person
$2,128
per person
Apr 10 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

4 out of 5
Save 100% on your flight
Price was $4,701, price is now $3,806 per person
$3,806
per person
Apr 10 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Palmgale House in Key West

Palmgale House in Key West

2 out of 5
Save 100% on your flight
Price was $12,357, price is now $10,007 per person
$10,007
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 2 days ago
$87
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Apr 13 from Tampa to Key West, returning Fri, Apr 17, priced at $87 found 2 days ago
Sun, Apr 5 - Wed, Apr 8
ATL
Atlanta
EYW
Key West
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sun, Apr 5 from Atlanta to Key West, returning Wed, Apr 8, priced at $217 found 1 hour ago
Wed, Mar 18 - Wed, Apr 1
PHL
Philadelphia
EYW
Key West
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Mar 18 from Philadelphia to Key West, returning Wed, Apr 1, priced at $222 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
1.44 mi from Sunset Key
$577 nightly
The price is $649 total per night
$649 total
Mar 24 - Mar 25
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.
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
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.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
2.83 mi from Sunset Key
$333 nightly
The price is $375 total per night
$375 total
Mar 5 - Mar 6
Total with taxes and fees
With a stay at Ibis Bay Beach Resort in Key West (Northside Resort), you'll be a 4-minute drive from Florida Keys Beaches and 5 minutes from Duval Street.
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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.

^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.