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 277 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in St. Augustine

Townhome in Orlando

4 bedrooms•3.5 baths

4.5

Home in Kissimmee

10 bedrooms•12 baths

$1,630 for 2 nights•

New

1628NP - 9 Bed - Whimsical Wonderland - SR015V

Home in Kissimmee

9 bedrooms•6.5 baths

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1240CP - 6 Bed - Simi's Sanctuary - W003

Home in Four Corners

6 bedrooms•5.5 baths

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Home in Davenport

11 bedrooms•12 baths

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Home in Kissimmee

6 bedrooms•5 baths

$694 for 2 nights•

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1761CV - 8 Bed - Amazonian Abode - SR012V

Home in Kissimmee

8 bedrooms•6.5 baths

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1742CV - 9 Bed - Champion's Chateau - SR011V

Home in Kissimmee

9 bedrooms•6.5 baths

New

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

Home in Kissimmee

9 bedrooms•9 baths

$4,409 for 3 nights•

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Waterpark! Princess Room! 9 mi 2 Disney! 1672

Home in Four Corners

9 bedrooms•5 baths

$1,650 for 3 nights•

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Value! Lazy River! Epic Resort 6 mi 2 Disney! 3180

Condo in Kissimmee

3 bedrooms•2 baths

$585 for 3 nights•

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Toy Story! Value! Epic Resort 6 mi 2 Disney! 2444

Home in Kissimmee

4 bedrooms•3 baths

$633 for 3 nights•

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Toy Story & Mickey! Resort 9 Mi 2 Disney! 9017

Townhome in Four Corners

5 bedrooms•4 baths

$684 for 3 nights•

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Star Wars! Minnie! Pool! Resort 6 mi 2 Disney-3007

Townhome in Kissimmee

4 bedrooms•3 baths

$633 for 3 nights•

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Star Wars! Mega Couch! Resort 6 mi 2 Disney! 8887

Home in Four Corners

8 bedrooms•5 baths

$1,551 for 3 nights•

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Relaxing 4 Bed Town Home with Splash Pool-1569PD

Townhome in Four Corners

4 bedrooms•3 baths

$633 for 3 nights•

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Featured vacation rentals in St. Augustine

Home in Four Corners

10 bedrooms•10 baths

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Luxury

Home in Kissimmee

10 bedrooms•11 baths

New

Luxury

Home in Kissimmee

10 bedrooms•11.5 baths

$6,600 for 3 nights•

4.6

Luxury

Home in Kissimmee

13 bedrooms•16 baths

$14,141 for 3 nights•

4.9

Private Theater! Star Wars! Water Slide! 6020

Home in Four Corners

14 bedrooms•11 baths

New

Property in Davenport

14 bedrooms•14 baths

5.0

Home in Kissimmee

8 bedrooms•7.5 baths

$2,932 for 3 nights•

3.9

Home in Kissimmee

11 bedrooms•10 baths

New

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

Townhome in Orlando

4 bedrooms•3.5 baths

4.5

Home in Kissimmee

10 bedrooms•12 baths

$1,630 for 2 nights•

New

Home in Kissimmee

9 bedrooms•6.5 baths

New

Home in Four Corners

6 bedrooms•5.5 baths

New

Home in Davenport

11 bedrooms•12 baths

New

Home in Kissimmee

6 bedrooms•5 baths

$694 for 2 nights•

New

Home in Kissimmee

8 bedrooms•6.5 baths

New

Home in Kissimmee

9 bedrooms•6.5 baths

New

View all homes

Most popular amenities for vacation rentals in St. Augustine

Basketball Court (19)

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 14506, W451E - The Glamorous Getaway, and 1628NP - 9 Bed - Whimsical Wonderland - SR015V. 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 277 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.