Stock Island Vacation Packages 2026 from $763

Stock Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Orchid Key Inn - Adults Only

Old Town Key West

Save 100% on your flight

$763

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the hot tub and free continental breakfast each morning. Self parking, a garden, and dry cleaning are also offered.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,912

per person

Dec 6 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West

$2,189

per person

Nov 30 - Dec 4

found 5 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Key West (EYW)

An outdoor pool is featured at this cottage, along with free WiFi in public areas and barbecue grills.

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachside

Save 100% on your flight

$2,462

per person

Jan 8 - Jan 15

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool is also provided.

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

Old Town Key West

Save 100% on your flight

$2,870

per person

Nov 29 - Dec 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this cottage, along with free WiFi in public areas.

Top Stock Island hotels deals

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$190 total

Oct 28 - Oct 29

Total with taxes and fees

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas and Internet in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

Pool

Pet friendly

The Perry Hotel & Marina Key West

7001 Shrimp Road Key West FL

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$188 total

Nov 2 - Nov 3

Total with taxes and fees

A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.

Aqua Lodges at Hurricane Hole Marina

5130 Overseas Hwy Key West FL

$258 nightly

$290 total

Oct 30 - Oct 31

Total with taxes and fees

This houseboat features a marina and free WiFi in public areas. Take advantage of the free self parking.

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

$255 nightly

$287 total

Oct 26 - Oct 27

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, poolside bar, and concierge services.

Pool

Hot Tub

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$246 total

Nov 15 - Nov 16

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$166 nightly

$187 total

Oct 26 - Oct 27

Total with taxes and fees

This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.

Don't see what you're looking for?

See all available properties in Stock Island

View all properties

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

A marina with various boats docked, calm water, and a clear sky.

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.

See properties

Frequently asked questions

How much are vacation packages to Stock Island?

With Travelocity vacation packages, you can live it up in Stock Island for a mere $763. Hotels, flights and experiences — we've got you. You'll save a bunch just by combining your bookings together. With all of that taken care of before you even set off, you won't have a care in the world.

How long should my Stock Island vacation be?

Most travelers spend about 5 nights in Stock Island, but how long you stay is your call. If you'd like to venture out and explore all the wonderful things this location has to offer, why not hang around for a bit longer?

Where can I get the best vacation package deals for Stock Island?

Travelocity is where to go to score an amazing Stock Island package deal. Take your pick of 400 airlines and 1,000,000 properties around the world and create a travel itinerary that fits your style. With almost endless choice, it's easy to organize your next big adventure.

Why should I book my Stock Island vacation bundle via Travelocity?

Nothing beats the feeling of knowing you've just picked up the best price available — that's our Price Match Guarantee. Add to that our inspiring range of magical destinations and 24/7 team of customer service professionals and you've got the formula for a stress-free vacation.

Can I save on my Stock Island car rental if I combine it with hotels and flights?

Certainly — bundle your car, flight and hotel into a Stock Island vacation package and you'll save tons. With so much to discover in the Stock Island area, that set of wheels will come in handy. Once you've buckled up, crank up the music and head to Zoo Miami, a top attraction approximately 110 mi from Stock Island.

What is the best time of year to go to Stock Island?

If you'd prefer to avoid expensive airfares, tourist masses and sold-out hotels, organize your escape outside of January, February and April. The quietest time to visit Stock Island is July, September and December. You'll find the highest hotel prices in and the lowest in .

Which airport is best for Stock Island?

The best airport for Stock Island is Key West Intl. Airport (EYW). You'll find it 2 mi northeast of the city center.

Where should I stay when visiting Stock Island?

If you're searching for somewhere to base yourself, take a look at the Casa Calypso - Beautiful Tropical Style House 3 King Beds Pool 2 Mi To Beach. It's the top choice for many visitors.