Best Luxury Family Vacation Spots in Hollywood, Florida

Hollywood, Florida is one of South Florida’s best-kept secrets for families who want sunshine, space, and sophistication without the chaos of Miami.

Set between Fort Lauderdale and Miami, Hollywood blends laid-back beach-town charm with upscale waterfront living. Think wide sandy beaches, the iconic Hollywood Beach Broadwalk, boat-filled canals, waterfront dining, and endless ways to keep kids entertained – all wrapped in warm Atlantic breezes.

If you’re searching for the best luxury family vacation rentals in Hollywood, this guide highlights homes that combine high-end design, space for everyone, and resort-style amenities. These aren’t just places to stay – they’re destinations in themselves.

1. Wander Hollywood Beach Villa

If your family loves boating, sunshine, and seamless indoor-outdoor living, Wander Hollywood Beach Villa delivers on every level.

Set on a rare 100-foot waterfront lot in the exclusive South Lake neighborhood, this architectural masterpiece blends luxury craftsmanship with relaxed Florida living. Floor-to-ceiling windows flood the home with light and frame sweeping water views, while private balconies off the master suite and second bedroom offer peaceful spots for morning coffee or sunset wind-downs.

Why families love it:

• Private pool overlooking the water

• Direct ocean access for boating days

• Chef’s kitchen with premium Miele appliances

• Spacious open-plan living for gathering together

• Quiet residential setting just minutes from Hollywood Beach dining and entertainment

During the day, head to Hollywood Beach and stroll the Broadwalk, rent bikes, or enjoy beachfront cafés. In the evening, return to your private waterfront retreat for a relaxed family dinner and poolside lounging.

For families wanting elegance, privacy, and water access, this is easily one of the best luxury vacation spots in Hollywood for families.

2. Wander Hollywood Beach

If your family vacation revolves around fun, this home turns every day into an event.

Wander Hollywood Beach is a luxurious waterfront retreat with breathtaking canal views and exceptional outdoor living. But what truly sets it apart is the entertainment factor.

Highlights include:

• Outdoor pool with basketball hoops

• Hot tub and fire pit for evening relaxation

• Spacious BBQ and dining area for alfresco meals

• Game room with pool table

• Private movie theatre for unforgettable family film nights

Spend mornings at the beach building sandcastles, afternoons paddleboarding along the Intracoastal, and evenings hosting your own movie premiere at home.

This is one of the best luxury family vacation spots in Hollywood for multi-generational trips where everyone wants something different – and everyone gets it.

3. Wander Fort Lauderdale Intracoastal

Just minutes from Hollywood, this Fort Lauderdale retreat offers calm canal-front living with space and style for the whole family.

Wander Fort Lauderdale Intracoastal features a private boat dock, a sparkling outdoor pool, a hot tub, and an expansive patio ideal for alfresco entertaining.

Inside, you’ll find a sleek fireplace, chef’s kitchen with wine cooler, and a bright contemporary design that makes downtime feel indulgent.

Ideal for:

• Families who want boat access

• Parents seeking a more refined atmosphere

• Evenings spent grilling and relaxing poolside

• Easy day trips to both Hollywood Beach and Las Olas Boulevard

The peaceful canal setting makes this one of the most serene luxury vacation spots in Hollywood, perfect for those looking to unwind while staying close to the action.

4. Wander Fort Lauderdale Waterfront

For families who love being on the water, this home blends relaxation and activity perfectly.

Wander Fort Lauderdale Waterfront features a private dock for kayaking or fishing, plus a patio with hot tub and BBQ area for easy outdoor living. Inside, you’ll find a fully equipped kitchen, cozy fireplace, and expansive water views from the living room.

Why it works for families:

• Direct water access

• Manageable size for smaller groups

• Outdoor gathering space

• Easy access to beaches, parks, and family attractions

Spend the morning exploring Anne Kolb Nature Center, take the kids to the beach, then return for sunset on the dock.

Why Hollywood Is Perfect for a Luxury Family Getaway

Hollywood strikes a rare balance, offering:

• Wide, family-friendly beaches

• A walkable beachfront promenade (the Broadwalk)

• Calm waters, perfect for paddleboarding and boating

• Easy access to Miami and Fort Lauderdale

• A more relaxed, less crowded atmosphere than South Beach

For families, that means fewer crowds, more space, and a slower pace, without sacrificing luxury.

And when you stay in a waterfront Wander home, you add privacy, premium design, and resort-style amenities to the mix.

FAQs for Families Planning a Vacation to Hollywood, Florida

What county of Florida is Hollywood in?

Hollywood is located in Broward County, in South Florida. It sits between Miami-Dade County to the south and Palm Beach County to the north, making it perfectly positioned for families who want easy access to multiple destinations without constantly packing up and moving hotels.

Its location in Broward County means you benefit from excellent beaches, well-maintained parks, strong infrastructure, and convenient transport links, all important factors when travelling with children.

Is Hollywood, Florida, safe for families?

Yes, Hollywood is widely considered a family-friendly and welcoming destination, particularly in residential waterfront neighbourhoods and around the Hollywood Beach area.

Families are drawn to:

• The pedestrian-friendly Hollywood Beach Broadwalk

• Calm stretches of sand, ideal for sandcastle building with your children

• Parks, nature centres, and outdoor activities

• A more relaxed atmosphere than nearby South Beach

As with any destination, it’s wise to stay in well-rated neighbourhoods and exercise normal travel awareness. Choosing a private luxury home in a residential waterfront area offers additional privacy, space, and comfort — especially for families travelling with young children or grandparents.

How far is Hollywood from Orlando, Florida?

Hollywood is approximately 230 miles from Orlando, which is about a 3.5 to 4-hour drive, depending on traffic.

For families dreaming of theme park magic, this means:

• Walt Disney World

• Universal Orlando Resort

• SeaWorld Orlando

…are all within reach for a day trip or an overnight extension to your stay.

Many families choose to split their holiday, enjoying theme park thrills in Orlando before retreating to Hollywood’s beaches and waterfront homes for a more relaxed, luxurious second half. It’s the perfect balance of excitement and downtime.

How far is Hollywood, Florida, from Miami?

Hollywood is just 20-25 miles north of Miami, typically around a 30-40 minute drive.

That makes it easy to visit:

• Miami’s cultural districts and museums

• Brickell and Wynwood for dining and art

• Professional sports games and major events

You get access to Miami’s energy, without having to stay in the middle of it.

How far is Hollywood, Florida, from Fort Lauderdale?

Hollywood is approximately 10-12 miles south of Fort Lauderdale, around a 15-20 minute drive.

This close proximity gives families convenient access to:

• Las Olas Boulevard

• Fort Lauderdale Beach

• Boat tours and water activities

• Family-friendly dining and attractions

It’s ideal for families who want variety without long travel days.

What airport is closest to Hollywood, Florida?

The closest airport is Fort Lauderdale-Hollywood International Airport (FLL).

It’s just 5-7 miles from Hollywood, typically a 10-15 minute drive, making arrivals and departures smooth and stress-free, especially with children.

Miami International Airport (MIA) is another option, about 30-40 minutes away, offering additional international routes.

For families, the short transfer from FLL is a major advantage. Less time in the car means more time by the pool, at the beach, or exploring the Broadwalk.

Book Your Family Getaway to Hollywood with Wander

Whether you’re planning a multi-generational reunion, a sunshine-filled school break, or a long-overdue family escape, Hollywood offers the perfect setting.

From private docks and chef’s kitchens to pools, game rooms, and home theatres, these homes redefine what a family vacation can look like.

If you’re searching for the best luxury vacation spots in Florida, these waterfront retreats deliver everything you need and then some.