Luxury Vacation Rentals with a Private Pool in Hollywood

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 66 private pool vacation rentals – enter your dates for availability.
Welcome to private poolside luxury in Hollywood

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.

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.

All homes in Hollywood

112 - Airbnb 5 property photo 1
Luxury

112 - Airbnb 5

8 bedrooms•5 baths
2,655 US dollars for 3 nights•
New

~$205 less than other sites

Private Home - Heated Pool - The Other Hollywood property photo 1

Private Home - Heated Pool - The Other Hollywood

3 bedrooms•2 baths
678 US dollars for 2 nights•

~$55 less than other sites

Family-Friendly Oasis with Heated Pool BBQ FirePit property photo 1

Family-Friendly Oasis with Heated Pool BBQ FirePit

4 bedrooms•2 baths
970 US dollars for 3 nights•

~$80 less than other sites

112 Dania Beach - New property photo 1

112 Dania Beach - New

7 bedrooms•5 baths
4,307 US dollars for 5 nights•

~$335 less than other sites

Waterfront Villa / Heated Pool, Gameroom property photo 1
Luxury

Waterfront Villa / Heated Pool, Gameroom

5 bedrooms•5 baths
3,272 US dollars for 3 nights•

~$265 less than other sites

Home in Hollywood property photo 1
Luxury

Home in Hollywood

8 bedrooms•6 baths
5,255 US dollars for 3 nights•

~$415 less than other sites

1244 Garfield property photo 1

1244 Garfield

5 bedrooms•3 baths
1,379 US dollars for 3 nights•

~$105 less than other sites

1759 - Airbnb 5 property photo 1

1759 - Airbnb 5

5 bedrooms•3 baths
1,692 US dollars for 3 nights•
New

~$130 less than other sites

View all homes
Discover more beyond the pool in Hollywood

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 112 - Airbnb 5, Private Home - Heated Pool - The Other Hollywood, and Family-Friendly Oasis with Heated Pool BBQ FirePit. 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 66 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.