Heartland Vacation Packages 2026 from $404

Heartland flight + hotel vacation packages

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

Marriott Hutchinson Island Resort & Beach Villas, Golf & Marina

$404

per person

Jan 24 - Jan 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to President Donald J. Trump Intl. Airport (DJT)

This smoke-free hotel features a golf course, a marina, and 3 restaurants. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. Enjoy the 3 outdoor pools and perks like free self parking and a free beach shuttle.

Turtle Reef Club

Hutchinson Island South

Save 100% on your flight

$1,282

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to President Donald J. Trump Intl. Airport (DJT)

This condo features an outdoor pool and a gym. Enjoy the outdoor tennis court and perks like free self parking and free WiFi. Laundry facilities and barbecue grills are also provided.

Beach Villas

Save 100% on your flight

$1,466

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to President Donald J. Trump Intl. Airport (DJT)

This smoke-free condo's golf course and 3 outdoor pools are some of the highlights. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free self parking and free WiFi.

Wyndham Grand Jupiter at Harbourside Place

Sea Palms

$1,410

per person

Jan 6 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to President Donald J. Trump Intl. Airport (DJT)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. You'll appreciate the gym, poolside bar, and concierge services.

Capt Hiram's Resort

$824

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to President Donald J. Trump Intl. Airport (DJT)

A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. A terrace, a garden, and a picnic area are also on offer.

Stay near popular Heartland attractions

Arcadia Rodeo Arena

8.6/10 (50 reviews)

Catch an event at Arcadia Rodeo Arena during your trip to Arcadia. Amble around the area's riverfront or experience its live music.

See properties

Frequently asked questions

How much are vacation packages to Heartland?

You'll be pleasantly surprised — you can recharge your batteries in Heartland for just $404. Here at Travelocity, we save you money and stress with our fantastic vacation packages. With experiences, hotels and flights all in one place, what are you waiting for?

Where can I get the best vacation package deals for Heartland?

Travelocity will be able to help you snag a terrific Heartland package deal. With as many as 400 partner airlines and 1,000,000 properties across the globe, there's no doubt you'll be able to craft the perfect itinerary.

Why should I book my Heartland vacation bundle with Travelocity?

Nothing beats the satisfaction of knowing you've just scored the best deal available — that's our Price Match Guarantee. Add to that our fantastic range of destinations and 24/7 team of customer service professionals and you've got the blueprint for a stress-free vacation.

Can I save on my Heartland car rental if I book it with my hotel or flight?

Bundling your bookings into a Heartland vacation package will save you a handsome sum. You can choose a car and flight; a car, flight and hotel; or a hotel and car. There's no better way to explore the greater Heartland region than with your own set of wheels. You can also add activities and experiences to your Travelocity package.

Which airport is best for Heartland?

Flying to Heartland typically means you'll be disembarking the plane at Southwest Florida Intl. Airport (RSW), the area's major hub.

What is there to do in Heartland?

You'll be happy to know Heartland is full to the brim with fabulous photo opportunities, however Seminole Casino Brighton and Kissimmee Prairie Preserve State Park are two favorites.