Luxury Vacation Rentals with a Private Pool in St. Augustine

Luxury Vacation Rentals with a Private Pool 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 4 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in St. Augustine

St. Augustine with Private Pool Near Downtown property photo 1

St. Augustine with Private Pool Near Downtown

4 bedrooms•2.5 baths
795 US dollars for 3 nights•

~$70 less than other sites

Ocean Views, Private Pool, Walk to Beach property photo 1

Ocean Views, Private Pool, Walk to Beach

4 bedrooms•2 baths
1,701 US dollars for 3 nights•
New

~$145 less than other sites

Oceanfront Family Condo in St. Augustine property photo 1

Oceanfront Family Condo in St. Augustine

3 bedrooms•2 baths
2,079 US dollars for 4 nights•

~$185 less than other sites

Vilano Villa, Walk 2 Beach, Water View, Wellness property photo 1

Vilano Villa, Walk 2 Beach, Water View, Wellness

5 bedrooms•3 baths
Welcome to private poolside luxury in St. Augustine

Welcome to private poolside luxury in St. Augustine

Settle into a collection of luxury private-pool vacation rentals in St. Augustine, where coastal elegance meets complete ease. Each home is selected for standout design, calming views, and a sense of privacy that feels worlds away yet perfectly placed for a refined escape.
Every residence centers life around its own pool, with thoughtful details such as heating, sun shelves, or a spillover spa. Inside, discover chef-ready kitchens, plush bedding, ultra fast WiFi, and quiet work nooks, all impeccably cleaned and supported by 24/7 concierge service. Book a Wander to enjoy hotel-grade polish in the comfort of a private home, made for lingering days and effortless evenings.

Available soon in St. Augustine

St. Augustine with Private Pool Near Downtown property photo 1

St. Augustine with Private Pool Near Downtown

4 bedrooms•2.5 baths
795 US dollars for 3 nights•

~$70 less than other sites

Ocean Views, Private Pool, Walk to Beach property photo 1

Ocean Views, Private Pool, Walk to Beach

4 bedrooms•2 baths
1,701 US dollars for 3 nights•
New

~$145 less than other sites

Vilano Villa, Walk 2 Beach, Water View, Wellness property photo 1

Vilano Villa, Walk 2 Beach, Water View, Wellness

5 bedrooms•3 baths
2,757 US dollars for 3 nights•

~$240 less than other sites

All homes in St. Augustine

St. Augustine with Private Pool Near Downtown property photo 1

St. Augustine with Private Pool Near Downtown

4 bedrooms•2.5 baths
795 US dollars for 3 nights•

~$70 less than other sites

Ocean Views, Private Pool, Walk to Beach property photo 1

Ocean Views, Private Pool, Walk to Beach

4 bedrooms•2 baths
1,701 US dollars for 3 nights•
New

~$145 less than other sites

Oceanfront Family Condo in St. Augustine property photo 1

Oceanfront Family Condo in St. Augustine

3 bedrooms•2 baths
2,079 US dollars for 4 nights•

~$185 less than other sites

Vilano Villa, Walk 2 Beach, Water View, Wellness property photo 1

Vilano Villa, Walk 2 Beach, Water View, Wellness

5 bedrooms•3 baths
View all homes

Highlights in St. Augustine

Discover America's oldest city, where centuries of Spanish history, pristine beaches, and brick-lined streets offer an enchanting coastal escape.
Castillo de San Marcos National Monument
St. Augustine Lighthouse & Maritime Museum
St. George Street
Lightner Museum
Ponce de Leon's Fountain of Youth Archaeological Park
St. Augustine Alligator Farm Zoological Park
Anastasia State 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.

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.

Most popular amenities for private pool vacation rentals in St. Augustine

Outdoor pool (4)
Sauna (1)
Jacuzzi (1)
Hot tub (1)
Outdoor shower (1)
Pool table (2)
Garden (4)
Bbq area (2)
Patio (2)
Dryer (4)
Fire pit (1)
Washer (4)
Fire place (1)
Oven (4)
Kitchen (4)
Balcony (1)

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Other popular amenities & vacation types in St. Augustine

Pet-friendly vacation rentals in St. Augustine
Family vacation rentals in St. Augustine
Large group vacation rentals in St. Augustine
Hot tub vacation rentals in St. Augustine
Discover more beyond the pool in St. Augustine

Discover more beyond the pool in St. Augustine

St. Augustine pairs Old World charm with ocean light in a way few places can. Cobblestone streets, the coquina stronghold of Castillo de San Marcos, and the glow of Flagler-era architecture set a cultured backdrop for unhurried days and elegant nights.
Across the bridge, Anastasia State Park stretches with broad beaches and wind-brushed dunes, while Vilano’s shoreline frames sunsets over the Intracoastal. Mild winters, a year-round arts scene, and the shimmering Nights of Lights make the city compelling in every season. This is why Wander’s luxury private-pool 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 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 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 private pool vacation rentals in St. Augustine?

Some of our most popular private pool vacation rentals in St. Augustine include St. Augustine with Private Pool Near Downtown, Ocean Views • Private Pool • Walk to Beach, and Oceanfront Family Condo in St. Augustine. 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 St. Augustine?

Wander offers 4 private pool 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 private pool vacation rentals in St. Augustine?

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

Do Wander’s private pool 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.