Luxury Vacation Rentals with a Private Pool in Hollywood

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 65 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Hollywood

Home in Hollywood

3 bedrooms•2 baths

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Home in Hollywood

4 bedrooms•2 baths

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Home in Dania Beach

8 bedrooms•5 baths

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Home in Dania Beach

8 bedrooms•5 baths

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Home in Fort Lauderdale

3 bedrooms•2 baths

Luxury

Home in Hollywood

5 bedrooms•5 baths

Luxury

Home in Fort Lauderdale

6 bedrooms•5 baths

Home in Davie

6 bedrooms•6.5 baths

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New

Welcome to private poolside luxury in Hollywood

Elevate your South Florida stay with Wander’s luxury private-pool vacation rentals in Hollywood, Florida. Each home delivers a private backyard oasis shaped for sun and seclusion, with heated pools, integrated spas, cushioned loungers, and tropical greenery that turns every afternoon into a retreat.

Inside, hotel-grade details shine: chef-ready kitchens, premium linens, ultra fast WiFi, smart climate control, and pristine housekeeping backed by 24/7 concierge. Select residences add outdoor kitchens, cabanas, fitness areas, and focused workspaces, blending high design with true-home comfort for restorative weekends and productive weekdays.

Available soon in Hollywood

Home in Hollywood

3 bedrooms•2 baths

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Home in Hollywood

4 bedrooms•2 baths

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Home in Dania Beach

8 bedrooms•5 baths

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Home in Dania Beach

8 bedrooms•5 baths

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Luxury

Home in Hollywood

5 bedrooms•5 baths

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Luxury

Home in Fort Lauderdale

6 bedrooms•5 baths

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Home in Davie

6 bedrooms•6.5 baths

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New

Condo in Hollywood

2 bedrooms•2 baths

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Featured private pool vacation rentals in Hollywood

Luxury

Home in Hollywood

5 bedrooms•5 baths

Luxury

Home in Fort Lauderdale

6 bedrooms•5 baths

Luxury

Home in Hollywood

8 bedrooms•6 baths

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Home in Hollywood

6 bedrooms•5 baths

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New

Home in Hollywood

5 bedrooms•2.5 baths

Highlights in Hollywood

Discover miles of pristine coastline, a vibrant brick-paved boardwalk, and a thriving downtown arts and culture scene in Hollywood, Florida.

Hollywood Beach Boardwalk

Anne Kolb Nature Center

ArtsPark at Young Circle

Seminole Hard Rock Hotel & Casino

Hollywood Beach

Downtown Hollywood Mural Project

Topeekeegee Yugnee Park

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Hollywood

Home in Hollywood

3 bedrooms•2 baths

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Home in Hollywood

4 bedrooms•2 baths

•

Home in Dania Beach

8 bedrooms•5 baths

•

Home in Dania Beach

8 bedrooms•5 baths

•

Home in Fort Lauderdale

3 bedrooms•2 baths

Luxury

Home in Hollywood

5 bedrooms•5 baths

Luxury

Home in Fort Lauderdale

6 bedrooms•5 baths

Home in Davie

6 bedrooms•6.5 baths

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New

View all homes

Most popular amenities for private pool vacation rentals in Hollywood

Exercise equipment (26)

Sauna (5)

Ocean view (2)

Beach essentials (32)

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Discover more beyond the pool in Hollywood

Set between the Atlantic and the Intracoastal Waterway, Hollywood pairs laid-back beach energy with a polished coastal pace. Broad, sandy shores and the palm-shaded Hollywood Beach Broadwalk welcome sunrise strolls and twilight bike rides, while canals weave through town with postcard views and ocean breezes.

Anne Kolb Nature Center’s mangroves, local art, and live music add variety without losing the relaxed mood. With year-round warmth and quick access to Fort Lauderdale and Miami, the location keeps travel effortless. This is why Wander’s luxury private-pool vacation rentals in Hollywood, Florida are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Hollywood

Why should I book a Wander in Hollywood over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.

Every home in Hollywood delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Hollywood?

Some of our most popular private pool vacation rentals in Hollywood include Private Home - Heated Pool - The Other Hollywood, Family-Friendly Oasis with Heated Pool BBQ FirePit, and 112 New. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Hollywood?

Wander offers 65 private pool vacation rentals in Hollywood, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Hollywood?

You can check-in to Wander private pool vacation rentals in Hollywood after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Hollywood have WiFi access?

Yes. Every Wander home in Hollywood has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.