Stock Island Vacation Packages
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Top Stock Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
CA $1,654
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (1,397 reviews)
Two concerns:
1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result.
2) concern may be equal parts
Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, etc. show up at check-in/out. Just quote the customer the true cost of their stay and avoid creating a frustration on behalf of the consumer.
Reviewed on Sep 1, 2026
Ella's Cottages - Key West Historic Inns
Old Town Key West
CA $1,919
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.4/10 Exceptional! (494 reviews)
It is located in the heart of he old district snd everything was so accessible without having to use our car. The property is only 1 block off Duval so,we had the advantage of,accessibility without the noise. The property is protected by foliage which makes it feel private and protected. The complimentary breakfast is lovely, and there is wine by the pool daily. Dwight welcomes guests upon arrival,and made us feel,at home. The beds are so comfy, and each cottage has its own flavor. I hope to return and stay at Ella’s Cottages again, Expedia does a great job helping us narrow down our priorities, amenities, location, etc. That enabled us to find Ella’s Cottages, which was perfect for us.
Reviewed on Sep 1, 2026
Ready to book your vacation to Stock Island?
Stock Island Hotel Deals
The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
Fully refundableReserve now, pay when you stay
CA $177
CA $284 total
Sep 22 - Sep 23
includes taxes & fees
Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
CA $158
CA $261 total
Sep 9 - Sep 10
includes taxes & fees
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
CA $198
CA $324 total
Sep 9 - Sep 10
includes taxes & fees
8.6/10 Excellent! (3,561 reviews)
"The resort fee is very expensive for what the resort has to offer for the guests. I will not rebook this resort the next time we are in Keywest. No shuttle services are offered. Nothing complimentary but two welcome drinks."
Reviewed on Sep 1, 2026
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.
Stay near popular Stock Island attractions
Key West Golf Club
8.4/10 (163 reviews)
Play a round of golf in Key West at Key West Golf Club, and enjoy other activities such as boating. Amble around the area's seaside or seek out the biking trails.
Stock Island Yacht Club & Marina
9.2/10 (8,513 reviews)
Explore the waterfront of Stock Island Yacht Club & Marina and enjoy activities such as boating in Key West. Discover the area's beautiful sunsets and lively bars.
Key West Tropical Forest and Botanical Garden
8.0/10 (9 reviews)
Enjoy the beautiful sunsets and explore Key West Tropical Forest and Botanical Garden, a lovely green space in Key West. Stroll along the area's beautiful beaches or experience its lively festivals.
Florida Keys Community College Library
After visiting Florida Keys Community College Library, make a plan to see the other sights and activities in Key West.
Tennesse Williams Fine Art Center
You can get tickets for a performance at Tennesse Williams Fine Art Center on your trip to Key West.
What to do in Stock Island
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $59
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $77
per adult
88% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
CA $109
per adult
94% of travellers recommend
Frequently asked questions
How much does a Stock Island vacation package cost?
Our Stock Island packages, which start at just CA $1,654, are the easiest way to save. Pick and choose your preferred hotels, flights and rental car to create your dream itinerary.
How do I get a cheap travel package to Stock Island?
Crafting your own Stock Island vacation package with Expedia is a simple way to save. We offer more than 550 air carriers and 1,000,000 hotel options globally. With such a fantastic range to choose from, you'll have no issues putting together your dream vacation.
Where should I stay in Stock Island?
With interesting attractions like Smathers Beach and Key West Art and Historical Society in this neighborhood, look for a hotel located near them. Key West Golf Club is another Stock Island hot spot that draws in the crowds.
What are the top hotels in Stock Island?
If it's your first visit to Stock Island, book a room at Welcome Aboard or Oceanfront 3 Bedroom Condo - 6 Pools. Both offer comfortable beds and are favorites with lots of travelers.
How far in advance should I book my Stock Island vacation?
It's always wise to book early. Air carriers usually advertise flights up to 12 months in advance, and this is a fantastic opportunity to pick up some rock-bottom prices. Boss just told you to take all your vacation days next month? That's fine too — Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Stock Island travel package include?
Flights, hotels and rental cars — we have them covered. With Expedia, you can shape your Stock Island package however you want. All you have to do is work out what you need. Once you've made your booking, you can add on fun things like activities and tours. The more you bundle, the greater the savings!
What should I know before booking a Stock Island travel package?
So many places to go, so many things to see. With a package, you can tick more of them off your list. Bundle your hotels, flights and rental cars and make big savings.
Can I choose my airline with a Stock Island Expedia vacation package?
Yes, the choice is yours. Expedia has access to more than 550 partner airlines throughout the world, so you can tailor your Stock Island vacation according to your needs and budget.
If I'm not able to travel, can I cancel my Stock Island vacation package?
Because we understand life can be unpredictable, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.
Explore a world of travel with Expedia
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- Flights from San Francisco (SFO) to Key West (EYW)
- Flights from St. Petersburg (PIE) to Key West (EYW)
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- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Toronto (YTZ) to Key West (EYW)
- Flights from Ottawa (YOW) to Key West (EYW)
- Flights from Bangor (BGR) to Key West (EYW)
- Flights from Hamilton (YHM) to Key West (EYW)
- Flights from London (YXU) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Regina (YQR) to Key West (EYW)
- Flights to Raccoon Key
- Flights from Syracuse (SYR) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Vancouver (YVR) to Key West (EYW)
- Flights from Richmond (RIC) to Key West (EYW)
- Flights from Montreal (YUL) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from Calgary (YYC) to Key West (EYW)
- Flights from Toronto (YYZ) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- Flights from Edmonton (YEG) to Key West (EYW)
- Flights from Kailua-Kona (KOA) to Key West (EYW)
- Flights from Halifax (YHZ) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from Daytona Beach (DAB) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Seattle (SEA) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from Naples (APF) to Key West (EYW)
- Flights from Stock Island
- Crane Point Museum and Nature Center
- Fort Zachary Taylor Historic State Park
- Key West Lighthouse and Keeper's Quarters Museum
- Harry S. Truman Little White House
- Veterans Memorial Park & Beach
- Mallory Square
- Sombrero Beach
- Marathon Vacations
- South Beach
- All inclusive Vacation Packages Key West
- Clarence S. Higgs Memorial Beach Park
- Duval Street
- Visit Key West
- Visit Downtown Key West
- Smathers Beach
- Visit Cow Key
- Seven Mile Bridge
- Mel Fisher Maritime Museum
- Key West Vacations
- Southernmost Point
- Sunset Park Beach
- Fort East Martello Museum and Gallery
- Calusa Beach
- Key West Shipwreck Museum
- Curry Hammock State Park
- Boca Chica Nude Beach
- Florida Keys Eco - Discovery Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
