Luxury Vacation Rentals 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 1,016 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in St. Augustine

Luxurious Villa with Pool & Games Room

15 bedrooms•14.5 baths

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New

~$230 less than other sites

4473 Monado

12 bedrooms•11.5 baths

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~$175 less than other sites

Townhome in Kissimmee

4 bedrooms•3 baths

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~$60 less than other sites

Large Home, Prime Location Orlando

8 bedrooms•5 baths

New

Retreat, Pool, Close to Disney

4 bedrooms•3 baths

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New

~$65 less than other sites

Family Townhouse near to Disney

4 bedrooms•3.5 baths

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New

~$55 less than other sites

Family Townhouse near to Disney

4 bedrooms•3.5 baths

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New

~$55 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

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~$55 less than other sites

Welcome to St. Augustine

Discover a refined escape with Wander’s luxury vacation rentals in St. Augustine. Each home brings modern elegance to America’s oldest city, offering generous living spaces, thoughtful design, and the privacy of a true coastal retreat. Guests can unwind in beautifully appointed interiors that balance comfort with sophistication.

Our St. Augustine properties are crafted for travelers who want both relaxation and style during their stay. From serene bedrooms to inviting communal areas, every corner reflects care and intention. With pristine cleaning, hotel grade amenities, and 24 hour concierge support, Wander raises the standard for anyone seeking luxury vacation rentals in St. Augustine.

Other destinations near St. Augustine

Flagler Beach

Palm Coast

Ponte Vedra Beach

Available soon in St. Augustine

Star Wars, Princess, Arcade Games, Disney 5334

4 bedrooms•3 baths

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New

~$95 less than other sites

BELLA VIDA (891MB) - Spacious HOME POOL/SPA

5 bedrooms•4 baths

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New

~$70 less than other sites

Storey Lake Pinnacle

2 bedrooms•2 baths

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~$35 less than other sites

Four Corners Pines

3 bedrooms•2.5 baths

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~$40 less than other sites

Luxury

500ML - 10 Bed - Michael's Manor - W001

10 bedrooms•11 baths

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New

~$405 less than other sites

2109PO - 6 Bed - Magic Mansion - ST049

6 bedrooms•6.5 baths

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New

~$145 less than other sites

Luxury

1759OB - 11 Bed - Celebrity Chateau - ST073

11 bedrooms•12 baths

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New

~$220 less than other sites

2029OC - 6 Bed - Intergalactic Island - ST100

6 bedrooms•6.5 baths

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New

~$140 less than other sites

Featured vacation rentals in St. Augustine

Themed Rooms, Mario Kart, Private Pool, Disney

15 bedrooms•14.5 baths

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New

~$380 less than other sites

Harry Potter, Toy Story, Game Room, Disney 2505

15 bedrooms•14 baths

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New

~$415 less than other sites

Luxury

NM501L Legends Palazzo

9 bedrooms•10.5 baths

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~$765 less than other sites

W172E- The Outstanding Oasis

11 bedrooms•10 baths

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New

~$460 less than other sites

Luxury

W402E - The Eclectic Colonial Estate

14 bedrooms•14 baths

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New

~$690 less than other sites

Luxury

BD012E - The Luxurious Bear's Den Oasis

6 bedrooms•6 baths

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New

~$510 less than other sites

1200GT - 10 Bed - Alyssa's Abode - W261

10 bedrooms•10 baths

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New

~$345 less than other sites

Luxury

W320E - The Entertainment Mansion

9 bedrooms•12 baths

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New

~$660 less than other sites

Highlights in St. Augustine

Explore centuries old architecture, sunlit waterfront views, and the storied charm that defines one of Florida’s most captivating coastal cities.

Castillo de San Marcos National Monument

St. George Street Historic District

Flagler College

Lightner Museum

St. Augustine Lighthouse & Maritime Museum

Anastasia State Park Beaches

Fountain of Youth Archaeological Park

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

Luxurious Villa with Pool & Games Room

15 bedrooms•14.5 baths

•

New

~$230 less than other sites

4473 Monado

12 bedrooms•11.5 baths

•

~$175 less than other sites

Townhome in Kissimmee

4 bedrooms•3 baths

•

~$60 less than other sites

Large Home, Prime Location Orlando

8 bedrooms•5 baths

New

Retreat, Pool, Close to Disney

4 bedrooms•3 baths

•

New

~$65 less than other sites

Family Townhouse near to Disney

4 bedrooms•3.5 baths

•

New

~$55 less than other sites

Family Townhouse near to Disney

4 bedrooms•3.5 baths

•

New

~$55 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

•

~$55 less than other sites

View all homes

Most popular amenities for vacation rentals in St. Augustine

Basketball court (26)

Discover more of St. Augustine

St. Augustine blends centuries of history with the easy charm of Florida’s shoreline. Cobblestone streets, preserved architecture, and a vibrant waterfront give the city a character that feels both intimate and full of depth. The area’s coastal light and warm breezes create an atmosphere that invites slow mornings, scenic walks, and quiet appreciation of its unique setting.

Visitors will find a destination shaped by culture, craft, and an unmistakable sense of place. Whether you are drawn to its heritage or its relaxed coastal mood, St. Augustine offers an experience that lingers long after your trip. This is why Wander's luxury vacation rentals in St. Augustine are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in St. Augustine

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

Wander offers a level of consistency and quality you won’t find with most 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 vacation rentals in St. Augustine?

Some of our most popular vacation rentals in St. Augustine include Luxurious 15-Bedroom Villa with Pool & Games Room, 4473 Monado, and BVT4 1000. 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 vacation rentals does Wander have available in St. Augustine?

Wander offers 1016 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 vacation rentals in St. Augustine?

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

Do Wander’s 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.