Stock Island Vacation Packages 2026 from $706

Stock Island flight + hotel vacation packages

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

Coconut Beach Resort

Old Town Key West

$706

per person

Sep 18 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

A private beach and an outdoor pool are featured at this smoke-free resort. Enjoy the hot tub and perks like free self parking and free WiFi. A computer station, dry cleaning, and luggage storage are also on offer.

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Old Town Key West

Save 100% on your flight

$2,479

per person

Oct 13 - Oct 20

found 1 day ago

Roundtrip non-stop 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.

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Key West Historic District

Save 100% on your flight

$1,578

per person

Oct 13 - Oct 20

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.

Easy Livin' by Avantstay Key West Home w/ Pool & BBQ Month Long Stays Only

Old Town Key West

Save 100% on your flight

$3,905

per person

Oct 17 - Oct 24

found 2 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

An outdoor pool, free self parking, and concierge services are featured at this cottage. WiFi in public areas is free. Barbecue grills are provided for your convenience.

The Key West Hotel

Key West Historic District

$838

per person

Sep 18 - Sep 20

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.

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

$194 nightly

$219 total

Sep 2 - Sep 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.

Pool

Pet friendly

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$200 nightly

$225 total

Aug 20 - Aug 21

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

$203 nightly

$228 total

Sep 1 - Sep 2

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

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$192 nightly

$216 total

Aug 16 - Aug 17

Total with taxes and fees

This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.

On private beach

Pool

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$153 total

Aug 17 - Aug 18

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

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$200 nightly

$225 total

Aug 30 - Aug 31

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

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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 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 $706. 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.