Luxury Vacation Rentals for Large Groups in St. Augustine

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 6 large group vacation rentals – enter your dates for availability.

Top-rated large group vacation rentals in St. Augustine

St. Augustine with Private Pool Near Downtown

4 bedrooms•2.5 baths

•

~$70 less than other sites

Sunshine Duo — Two Coastal Homes Just Down the Road

6 bedrooms•4 baths

•

~$155 less than other sites

Luxury

Treasure & Tide Escape

5 bedrooms•4 baths

•

New

~$190 less than other sites

The SkyDeck Surf House

6 bedrooms•5 baths

•

~$240 less than other sites

Vilano Villa, Walk 2 Beach, Water View, Wellness

5 bedrooms•3 baths

Luxury

Seaside Serenity - Pool Table, Hot Tub, Luxury

6 bedrooms•4 baths

•

~$440 less than other sites

Welcome to your large group retreat in St. Augustine

Gather your favorite people in America’s oldest city with space to spread out and connect. Wander offers luxury vacation rentals in St. Augustine designed for large groups, from multigenerational getaways to corporate offsites.

Expect expansive great rooms, multiple ensuite bedrooms, chef ready kitchens, oversized tables, and seamless indoor to outdoor living. Many homes feature private pools, hot tubs, game spaces, and dedicated work areas with ultra fast WiFi.

Each stay delivers hotel grade service, pristine cleaning, and 24/7 concierge support, so logistics feel effortless and the photos match reality. When you book a Wander, you get the style of a luxury hotel with the comfort of a private home, all tailored to groups.

Available soon in St. Augustine

St. Augustine with Private Pool Near Downtown

4 bedrooms•2.5 baths

•

~$70 less than other sites

Sunshine Duo — Two Coastal Homes Just Down the Road

6 bedrooms•4 baths

•

~$155 less than other sites

Luxury

Treasure & Tide Escape

5 bedrooms•4 baths

•

New

~$190 less than other sites

The SkyDeck Surf House

6 bedrooms•5 baths

•

~$240 less than other sites

Vilano Villa, Walk 2 Beach, Water View, Wellness

5 bedrooms•3 baths

•

~$240 less than other sites

Featured large group vacation rentals in St. Augustine

The SkyDeck Surf House

6 bedrooms•5 baths

•

~$240 less than other sites

Luxury

Seaside Serenity - Pool Table, Hot Tub, Luxury

6 bedrooms•4 baths

•

~$440 less than other sites

Highlights in St. Augustine

Gather your group to explore America's oldest city, where historic fortresses, sandy beaches, and lively group tours await your crowd.

Castillo de San Marcos National Monument

St. Augustine Lighthouse & Maritime Museum

St. Augustine Alligator Farm Zoological Park

Lightner Museum

St. Augustine Beach

Colonial Quarter

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 St. Augustine

St. Augustine with Private Pool Near Downtown

4 bedrooms•2.5 baths

•

~$70 less than other sites

Sunshine Duo — Two Coastal Homes Just Down the Road

6 bedrooms•4 baths

•

~$155 less than other sites

Luxury

Treasure & Tide Escape

5 bedrooms•4 baths

•

New

~$190 less than other sites

The SkyDeck Surf House

6 bedrooms•5 baths

•

~$240 less than other sites

Vilano Villa, Walk 2 Beach, Water View, Wellness

5 bedrooms•3 baths

Luxury

Seaside Serenity - Pool Table, Hot Tub, Luxury

6 bedrooms•4 baths

•

~$440 less than other sites

View all homes

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Discover more large groups activities in St. Augustine

St. Augustine blends centuries of Spanish heritage with Atlantic coastal beauty. Cobblestone streets, the iconic Castillo de San Marcos, and a lively bayfront create an unforgettable setting, while winter’s Nights of Lights turns the city into a glowing celebration.

Beyond the historic core, wide sandy beaches stretch from Vilano to Anastasia. Charter a boat on Matanzas Bay, paddle through quiet marshlands, or play world class golf nearby. The region’s arts festivals and live music bring fresh energy in every season.

With history, coastline, and culture in easy reach, this is why Wander's luxury vacation rentals in St. Augustine are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in St. Augustine

Why should I book a Wander in St. Augustine over other large group vacation rentals?

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

Every home in St. Augustine 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 large group vacation rentals in St. Augustine?

Some of our most popular large group vacation rentals in St. Augustine include St. Augustine with Private Pool Near Downtown, Sunshine Duo — Two Coastal Homes Just Down the Road, and Treasure & Tide Escape. 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 large group vacation rentals does Wander have available in St. Augustine?

Wander offers 6 large group vacation rentals in St. Augustine, 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 large group vacation rentals in St. Augustine?

You can check-in to Wander large group vacation rentals in St. Augustine after 4.00pm and check-out before 10.00am.

Do Wander’s large group vacation rentals in St. Augustine have WiFi access?

Yes. Every Wander home in St. Augustine 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.