Cheap Vacations in Stock Island

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Stock Island vacations

Price found within the past 48 hours. Click for updated prices.
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 $3,030, price is now $2,527 per person
$2,527
per person
Apr 16 - Apr 21
just found
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)

3-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 $1,029, price is now $775 per person
$775
per person
Apr 22 - Apr 25
found 1 day 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 $2,580, price is now $1,841 per person
$1,841
per person
Apr 23 - Apr 26
found 19 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,653, price is now $1,220 per person
$1,220
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $1,187, price is now $920 per person
$920
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,318, price is now $1,032 per person
$1,032
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,279, price is now $1,025 per person
$1,025
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,486, price is now $1,193 per person
$1,193
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,019, price is now $827 per person
$827
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $1,833, price is now $1,495 per person
$1,495
per person
Apr 23 - Apr 26
found 19 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $1,809, price is now $1,476 per person
$1,476
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,843, price is now $1,521 per person
$1,521
per person
Apr 23 - Apr 26
found 19 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
Price was $1,612, price is now $1,334 per person
$1,334
per person
Apr 23 - Apr 26
found 19 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,497, price is now $1,147 per person
$1,147
per person
Apr 27 - May 1
found 1 day 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 $4,699, price is now $3,298 per person
$3,298
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $1,725, price is now $1,232 per person
$1,232
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $2,442, price is now $1,790 per person
$1,790
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $1,784, price is now $1,376 per person
$1,376
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,554, price is now $1,213 per person
$1,213
per person
Apr 27 - May 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Price was $1,564, price is now $1,225 per person
$1,225
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,436, price is now $1,917 per person
$1,917
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $2,533, price is now $2,068 per person
$2,068
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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
Save 100% on your flight
Price was $2,877, price is now $2,356 per person
$2,356
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Price was $1,827, price is now $1,508 per person
$1,508
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)

5-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
Save 100% on your flight
Price was $1,723, price is now $1,073 per person
$1,073
per person
Apr 30 - May 5
found 12 hours ago
Roundtrip 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 $3,280, price is now $1,872 per person
$1,872
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,979, price is now $1,210 per person
$1,210
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,396, price is now $1,609 per person
$1,609
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,879, price is now $1,274 per person
$1,274
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,795, price is now $1,250 per person
$1,250
per person
Apr 23 - Apr 28
found 13 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,694, price is now $1,885 per person
$1,885
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Save 100% on your flight
Price was $2,522, price is now $1,805 per person
$1,805
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Eden House

Eden House

4 out of 5
Save 100% on your flight
Price was $2,095, price is now $1,500 per person
$1,500
per person
Apr 30 - May 5
found 12 hours ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Save 100% on your flight
Price was $1,498, price is now $1,074 per person
$1,074
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)

6-7 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
Save 100% on your flight
Price was $2,071, price is now $1,278 per person
$1,278
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $6,769, price is now $4,499 per person
$4,499
per person
Apr 9 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,242, price is now $1,606 per person
$1,606
per person
Apr 9 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Save 100% on your flight
Price was $2,079, price is now $1,513 per person
$1,513
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,954, price is now $1,429 per person
$1,429
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $3,079, price is now $2,295 per person
$2,295
per person
Apr 7 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,837, price is now $2,133 per person
$2,133
per person
Apr 7 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
New Coastal Rose - Bright Loft With High Ceilings

New Coastal Rose - Bright Loft With High Ceilings

2 out of 5
Save 100% on your flight
Price was $3,656, price is now $2,751 per person
$2,751
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 $2,150, price is now $1,630 per person
$1,630
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Save 100% on your flight
Price was $1,874, price is now $1,434 per person
$1,434
per person
Apr 9 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
Save 100% on your flight
Price was $1,870, price is now $1,432 per person
$1,432
per person
Apr 7 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $2,228, price is now $1,734 per person
$1,734
per person
Apr 9 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 4 days ago
$87
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Apr 13 from Tampa to Key West, returning Fri, Apr 17, priced at $87 found 4 days ago
Tue, Mar 24 - Wed, Mar 25
ATL
Atlanta
EYW
Key West
$175 Roundtrip, found 10 hours ago
$175
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Tue, Mar 24 from Atlanta to Key West, returning Wed, Mar 25, priced at $175 found 10 hours ago
Sun, Mar 29 - Thu, Apr 2
BOS
Boston
EYW
Key West
$250 Roundtrip, found 3 days ago
$250
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sun, Mar 29 from Boston to Key West, returning Thu, Apr 2, priced at $250 found 3 days ago

Top rated hotels for your Stock Island vacation

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
$426 nightly
The price is $479 total per night
$479 total
Apr 5 - Apr 6
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
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
3.89 mi from city center
$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.
Pool
Spa
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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.