Stock Island Vacation Packages 2026 from $988

Stock Island flight + hotel vacation packages

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

Paradise Inn Key West - Adults Only

Old Town Key West

$988

per person

Dec 13 - Dec 18

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a hot tub. Enjoy the free self-serve breakfast each morning. Self parking, a terrace, and a garden are also offered.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,805

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip non-stop 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.

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

Old Town Key West

Save 100% on your flight

$2,491

per person

Nov 19 - Nov 23

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.

The Gardens Hotel

Old Town Key West

$1,663

per person

Nov 26 - Nov 30

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.

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$1,186

per person

Nov 20 - Nov 25

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.

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

$182 nightly

$205 total

Sep 27 - Sep 28

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

$172 nightly

$193 total

Sep 27 - Sep 28

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

Aqua Lodges at Hurricane Hole Marina

5130 Overseas Hwy Key West FL

$243 nightly

$274 total

Sep 28 - Sep 29

Total with taxes and fees

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

Parking included

Free WiFi

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$189 total

Sep 27 - Sep 28

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

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$258 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, free WiFi in public areas, and laundry service. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.

Pool

Spa

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$265 nightly

$298 total

Sep 27 - Sep 28

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

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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.

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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 $988. 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.