Luxury Vacation Rentals with a Private Pool in Williamsburg

Luxury Vacation Rentals with a Private Pool in Williamsburg

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 8 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Williamsburg

EV 6283 - Paradiso Grand Royale property photo 1

EV 6283 - Paradiso Grand Royale

15 bedrooms•14.5 baths
2,689 US dollars for 3 nights•
New

~$235 less than other sites

EV 5818 - Paradiso Royale Estate property photo 1

EV 5818 - Paradiso Royale Estate

15 bedrooms•14.5 baths
2,689 US dollars for 3 nights•
New

~$235 less than other sites

5809Highseas property photo 1

5809Highseas

12 bedrooms•10 baths
2,625 US dollars for 3 nights•
New

~$230 less than other sites

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818 property photo 1

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818

15 bedrooms•14.5 baths
4,302 US dollars for 4 nights•
New

~$380 less than other sites

5 Themed Rooms, Bunk Slide, Private Pool 6283 property photo 1

5 Themed Rooms, Bunk Slide, Private Pool 6283

15 bedrooms•16.5 baths
4,702 US dollars for 4 nights•
New

~$415 less than other sites

Spacious and Luxury - Near Sea World property photo 1

Spacious and Luxury - Near Sea World

8 bedrooms•8 baths
1,301 US dollars for 3 nights•
New

~$110 less than other sites

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818 property photo 1

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818

15 bedrooms•14.5 baths
4,323 US dollars for 4 nights•
New

~$380 less than other sites

5 Themed Rooms, Bunk Slide, Private Pool 6283 property photo 1

5 Themed Rooms, Bunk Slide, Private Pool 6283

15 bedrooms•16.5 baths
4,702 US dollars for 4 nights•
New

~$415 less than other sites

Welcome to private poolside luxury in Williamsburg

Welcome to private poolside luxury in Williamsburg

Settle into Wander’s luxury vacation rentals with private pools in Williamsburg, where resort polish meets the comfort of a private home. Each space is designed for effortless indoor and outdoor living, so your day can flow from airy lounges to your own pool under Florida skies.
Expect hotel-grade details throughout: ultra fast WiFi, immaculate cleaning, plush linens, smart home touches, and responsive 24/7 concierge support. Open layouts, modern kitchens, and dedicated work areas make it easy to blend relaxation with productivity.
Book with confidence. Our homes look exactly like the photos and are professionally operated, so all you need to plan is your next poolside moment.

Available soon in Williamsburg

EV 6283 - Paradiso Grand Royale property photo 1

EV 6283 - Paradiso Grand Royale

15 bedrooms•14.5 baths
2,689 US dollars for 3 nights•
New

~$235 less than other sites

EV 5818 - Paradiso Royale Estate property photo 1

EV 5818 - Paradiso Royale Estate

15 bedrooms•14.5 baths
2,689 US dollars for 3 nights•
New

~$235 less than other sites

5809Highseas property photo 1

5809Highseas

12 bedrooms•10 baths
2,625 US dollars for 3 nights•
New

~$230 less than other sites

Spacious and Luxury - Near Sea World property photo 1

Spacious and Luxury - Near Sea World

8 bedrooms•8 baths
1,301 US dollars for 3 nights•
New

~$110 less than other sites

Featured private pool vacation rentals in Williamsburg

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818 property photo 1

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818

15 bedrooms•14.5 baths
4,302 US dollars for 4 nights•
New

~$380 less than other sites

5 Themed Rooms, Bunk Slide, Private Pool 6283 property photo 1

5 Themed Rooms, Bunk Slide, Private Pool 6283

15 bedrooms•16.5 baths
4,702 US dollars for 4 nights•
New

~$415 less than other sites

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818 property photo 1

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818

15 bedrooms•14.5 baths
4,323 US dollars for 4 nights•
New

~$380 less than other sites

5 Themed Rooms, Bunk Slide, Private Pool 6283 property photo 1

5 Themed Rooms, Bunk Slide, Private Pool 6283

15 bedrooms•16.5 baths
4,702 US dollars for 4 nights•
New

~$415 less than other sites

Highlights in Williamsburg

Perfect for theme park enthusiasts, Williamsburg offers easy access to world-class marine life encounters, thrilling rollercoasters, and vibrant entertainment hubs.
SeaWorld Orlando
Discovery Cove
Aquatica Orlando
ICON Park
Universal Orlando Resort
Pointe Orlando

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 Williamsburg

EV 6283 - Paradiso Grand Royale property photo 1

EV 6283 - Paradiso Grand Royale

15 bedrooms•14.5 baths
2,689 US dollars for 3 nights•
New

~$235 less than other sites

EV 5818 - Paradiso Royale Estate property photo 1

EV 5818 - Paradiso Royale Estate

15 bedrooms•14.5 baths
2,689 US dollars for 3 nights•
New

~$235 less than other sites

5809Highseas property photo 1

5809Highseas

12 bedrooms•10 baths
2,625 US dollars for 3 nights•
New

~$230 less than other sites

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818 property photo 1

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818

15 bedrooms•14.5 baths
4,302 US dollars for 4 nights•
New

~$380 less than other sites

5 Themed Rooms, Bunk Slide, Private Pool 6283 property photo 1

5 Themed Rooms, Bunk Slide, Private Pool 6283

15 bedrooms•16.5 baths
4,702 US dollars for 4 nights•
New

~$415 less than other sites

Spacious and Luxury - Near Sea World property photo 1

Spacious and Luxury - Near Sea World

8 bedrooms•8 baths
1,301 US dollars for 3 nights•
New

~$110 less than other sites

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818 property photo 1

Potter Gameroom, Avatar Theater, 5 Theme Rooms 5818

15 bedrooms•14.5 baths
4,323 US dollars for 4 nights•
New

~$380 less than other sites

5 Themed Rooms, Bunk Slide, Private Pool 6283 property photo 1

5 Themed Rooms, Bunk Slide, Private Pool 6283

15 bedrooms•16.5 baths
4,702 US dollars for 4 nights•
New

~$415 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Williamsburg

Outdoor pool (8)
Jacuzzi (4)
Hot tub (4)
Heated pool (4)
Pool table (1)
Garden (4)
Dryer (8)
Bbq area (1)
Kitchen (8)
Dishwasher (8)
Microwave (8)
Wifi (8)
Coffee maker (6)
Washer (4)
Oven (4)
Bathtub (4)

More popular private pool destinations near Williamsburg

Private pool vacation rentals in Kissimmee
Private pool vacation rentals in Orlando
Private pool vacation rentals in Orlando,
Private pool vacation rentals in Reunion
Private pool vacation rentals in Loughman
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Private pool vacation rentals in Davenport
Private pool vacation rentals in Clermont

Other popular amenities & vacation types in Williamsburg

Family vacation rentals in Williamsburg
Large group vacation rentals in Williamsburg
Discover more beyond the pool in Williamsburg

Discover more beyond the pool in Williamsburg

Tucked just south of Orlando’s headline attractions, Williamsburg delivers a calm, well kept setting with quick connections to International Drive, SeaWorld, and the Orange County Convention Center. Tree-lined streets, pocket lakes, and wide sidewalks set an easygoing pace between outings.
Arrive with ease via Orlando International Airport in about 20 minutes, then spend your days sampling Dr. Phillips dining, outlet shopping, golf, or sunset strolls by the water. Sunshine is reliable year-round, ideal for long afternoons outdoors and golden hour walks. This is why Wander’s luxury vacation rentals in Williamsburg are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Williamsburg

Why should I book a Wander in Williamsburg 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 Williamsburg 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 Williamsburg?

Some of our most popular private pool vacation rentals in Williamsburg include EV_6283 - Paradiso Grand Royale, EV_5818 - Paradiso Royale Estate, and 5809Highseas. 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 Williamsburg?

Wander offers 8 private pool vacation rentals in Williamsburg, 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 Williamsburg?

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

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

Yes. Every Wander home in Williamsburg 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.