Stock Island Vacation Packages 2026 from $1,110

Stock Island flight + hotel vacation packages

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

Hyatt Vacation Club at Beach House, Key West

$1,110

per person

Nov 29 - Dec 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, concierge services, and barbecue grills are also on offer.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,296

per person

Nov 9 - Nov 12

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.

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,619

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

2 outdoor pools, 2 bars/lounges, and a restaurant are among this bed & breakfast's featured amenities. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy the free cooked-to-order breakfast each morning.

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

Old Town Key West

Save 100% on your flight

$3,182

per person

Dec 5 - Dec 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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

Fitch Lodge - Key West Historic Inns

Key West Historic District

Save 100% on your flight

$1,600

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Concierge services are provided for your convenience.

Top Stock Island hotels deals

The Perry Hotel & Marina Key West

7001 Shrimp Road Key West FL

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$207 total

Sep 20 - Sep 21

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.

Pool

Pet friendly

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$179 total

Sep 23 - Sep 24

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

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$269 total

Sep 28 - Sep 29

Total with taxes and fees

A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.

Pool

Spa

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$180 total

Sep 20 - Sep 21

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.

Pool

Hot Tub

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$234 nightly

$263 total

Oct 1 - Oct 2

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

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$146 total

Sep 20 - Sep 21

Total with taxes and fees

This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.

On private beach

Pool

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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.

Stay near popular Stock Island attractions

A serene landscape with a pond, palm trees, and a golf course.

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.

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 $1,110. 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.