Stock Island Vacation Packages 2026 from $825

Stock Island flight + hotel vacation packages

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

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$825

per person

Mar 9 - Mar 13

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.

The Key West Hotel

Key West Historic District

$2,227

per person

Feb 10 - Feb 15

found 19 hours 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.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$2,390

per person

Feb 10 - Feb 15

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,522

per person

Feb 10 - Feb 15

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,520

per person

Feb 10 - Feb 15

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.

Top Stock Island hotels deals

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$265 nightly

$298 total

Jan 8 - Jan 9

Total with taxes and fees

Pool

Pet friendly

The Perry Hotel & Marina Key West

7001 Shrimp Road Key West FL

$378 nightly

$425 total

Jan 22 - Jan 23

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

Aqua Lodges at Hurricane Hole Marina

5130 Overseas Hwy Key West FL

$283 nightly

$319 total

Jan 11 - Jan 12

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

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$302 nightly

$340 total

Jan 19 - Jan 20

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

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$283 nightly

$318 total

Jan 8 - Jan 9

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 an arcade/game room, 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

$406 nightly

$457 total

Jan 13 - Jan 14

Total with taxes and fees

Pool

Spa

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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.

Popular places to visit

Stock Island Yacht Club & Marina

4.5/5(2,254 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 Golf Club

4/5(52 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.

Key West Tropical Forest and Botanical Garden

4/5(5 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 seaside or experience its lively festivals.

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 $825. 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.