Cheap Vacations in Stock Island

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Stock Island vacations

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,606, price is now $1,218 per person
$1,218
per person
Apr 4 - Apr 9
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)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $2,016, price is now $1,604 per person
$1,604
per person
Apr 4 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)

3-night Stock Island 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 $973, price is now $805 per person
$805
per person
Apr 20 - Apr 23
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
Price was $2,808, price is now $2,053 per person
$2,053
per person
Apr 10 - Apr 13
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 $1,827, price is now $1,382 per person
$1,382
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Price was $1,251, price is now $966 per person
$966
per person
Apr 10 - Apr 13
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 $1,274, price is now $993 per person
$993
per person
Apr 20 - Apr 23
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 $1,277, price is now $1,005 per person
$1,005
per person
Apr 20 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $1,520, price is now $1,244 per person
$1,244
per person
Apr 20 - Apr 23
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 $2,204, price is now $1,813 per person
$1,813
per person
Apr 10 - Apr 13
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
Price was $2,055, price is now $1,700 per person
$1,700
per person
Apr 10 - Apr 13
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 $2,048, price is now $1,709 per person
$1,709
per person
Apr 10 - Apr 13
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 $1,698, price is now $1,418 per person
$1,418
per person
Apr 10 - Apr 13
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
Save 100% on your flight
Price was $1,959, price is now $1,647 per person
$1,647
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)

4-night Stock Island 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
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)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $2,084, price is now $1,501 per person
$1,501
per person
Apr 15 - Apr 19
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 $1,975, price is now $1,426 per person
$1,426
per person
Apr 15 - Apr 19
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 $3,129, price is now $2,269 per person
$2,269
per person
Apr 15 - Apr 19
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
Price was $1,899, price is now $1,411 per person
$1,411
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Price was $1,608, price is now $1,229 per person
$1,229
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip 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 $2,290, price is now $1,801 per person
$1,801
per person
Apr 15 - Apr 19
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 $3,778, price is now $3,002 per person
$3,002
per person
Apr 15 - Apr 19
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 $2,745, price is now $2,213 per person
$2,213
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip 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 $1,650, price is now $1,340 per person
$1,340
per person
Apr 15 - Apr 19
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 $2,050, price is now $1,665 per person
$1,665
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)

5-night Stock Island vacations

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,606, price is now $1,218 per person
$1,218
per person
Apr 4 - Apr 9
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 21 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
Price was $2,979, price is now $2,062 per person
$2,062
per person
Apr 4 - Apr 9
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 $2,643, price is now $1,945 per person
$1,945
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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)
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)
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)
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)
Ocean Front 2BR Residence

Ocean Front 2BR Residence

2 out of 5
Price was $4,841, price is now $3,757 per person
$3,757
per person
Apr 20 - Apr 25
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
Price was $3,985, price is now $3,132 per person
$3,132
per person
Apr 4 - Apr 9
found 1 day ago
Roundtrip 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 $10,957, price is now $8,611 per person
$8,611
per person
Apr 20 - Apr 25
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 $2,038, price is now $1,611 per person
$1,611
per person
Apr 4 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)

6-7 night Stock Island 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 $1,698, price is now $1,366 per person
$1,366
per person
Apr 8 - Apr 14
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 $2,644, 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 Key West Hotel

The Key West Hotel

2.5 out of 5
Price was $6,735, price is now $4,518 per person
$4,518
per person
Apr 8 - Apr 14
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)
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)
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
Price was $3,016, price is now $2,341 per person
$2,341
per person
Apr 18 - Apr 24
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)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $2,754, price is now $2,169 per person
$2,169
per person
Apr 8 - Apr 14
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 $2,515, price is now $1,986 per person
$1,986
per person
Apr 8 - Apr 14
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
Price was $3,102, price is now $2,452 per person
$2,452
per person
Apr 8 - Apr 14
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 $2,567, price is now $2,032 per person
$2,032
per person
Apr 8 - Apr 14
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 $2,386, price is now $1,896 per person
$1,896
per person
Apr 8 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)

Flight deals to Stock Island

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
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
Thu, Apr 16 - Sun, Apr 19
ATL
Atlanta
EYW
Key West
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Apr 16 from Atlanta to Key West, returning Sun, Apr 19, priced at $230 found 1 day ago

Top rated hotels for your Stock Island vacation

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
1.01 mi from city center
$334 nightly
The price is $375 total per night
$375 total
Apr 4 - Apr 5
Total with taxes and fees
When you stay at Oceans Edge Key West Resort, Hotel & Marina in Key West, you'll be next to a golf course, within a 15-minute drive of Duval Street and Smathers Beach.
Pool
Pet friendly
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
Free Cancellation
Reserve now, pay when you stay
0.54 mi from city center
$450 nightly
The price is $506 total per night
$506 total
Mar 22 - Mar 23
Total with taxes and fees
When you stay at The Perry Hotel & Marina Key West in Key West, you'll be on the waterfront, within a 5-minute drive of Stock Island Yacht Club & Marina and Key West Golf Club.
Pool
Pet friendly
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy Key West FL
0.41 mi from city center
$346 nightly
The price is $389 total per night
$389 total
Mar 15 - Mar 16
Total with taxes and fees
With a stay at this houseboat in Key West, you'll be within a 10-minute drive of Duval Street and Smathers Beach.
Parking included
Free WiFi
Don't see what you're looking for?
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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.