Skip to main content
Entire home

The Road to the Triple Crown - Gulf Views with Large Private Pool Area

Photo gallery for The Road to the Triple Crown - Gulf Views with Large Private Pool Area

The Road to the Triple Crown - Dune Allen Beach - Back Patio & Private Pool
The Road to the Triple Crown - Dune Allen Beach - Exterior
The Road to the Triple Crown - Dune Allen Beach - Rooftop Balcony
The Road to the Triple Crown - Dune Allen Beach - Living Room
The Road to the Triple Crown - Dune Allen Beach - Living Room

Reviews

7.0 out of 10
Good
12 bedrooms10 bathroomsSleeps 29

Popular amenities

  • Private pool
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Rooms & beds

12 bedrooms (sleeps 29)

Bunk Room - Two Twin/Twin

2 Single Bunk Beds

Bunk Room - Two Twin/Twin Bunks - (Belmont)

2 Single Bunk Beds

King Bedroom

1 King Bed

King Bedroom

1 King Bed

King Bedroom

1 King Bed

King Bedroom

1 King Bed

King Bedroom

1 King Bed

King Bedroom - (Belmont)

1 King Bed

King Bedroom - (Belmont)

1 King Bed

King Bedroom - (Belmont)

1 King Bed

King Bedroom - (Belmont)

1 King Bed

Queen Bedroom - (Belmont)

1 Queen Bed

10 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Bathroom 6

Toilet · Shower only

Bathroom 7

Toilet · Shower only

Bathroom 8

Toilet · Shower only

Bathroom 9

Toilet · Shower only

Bathroom 10

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Dining area

About this property

The Road to the Triple Crown - Gulf Views with Large Private Pool Area

The Road to the Triple Crown - Luxury Vacation Rentals on 30A with Private Pools and Beachviews
Favorite features
- 2 Private Pools - Heated Pools $150 /Night (Available Oct-April Only)
- Elevator to all main floors
- 2 Observation Decks
- Beachviews
- Pet Friendly
- 8 Complementary Bikes

More about The Road to the Triple Crown
Sleeping a whopping 29 guests across 12 bedrooms, this is the place to be if you have a large event! Comprised of two beautiful 5,800 square ft. homes, The Belmont at the Beach and The Preakness at the Beach, guests will enjoy over 11,000 square feet of combined living space, a choice of two private pools, two observation decks and beautiful beach views, all just a three minute walk to the sandy shores. The Road to The Triple Crown is THE venue for multi-family getaways, corporate retreats, weddings, and large celebrations of any kind. With an elevator to all main floors and pets allowed, The Road to the Triple Crown offers inclusivity for everyone in your party without worrying about those that struggle with stairs, or guests that need to bring their fur babies. The Road to the Triple Crown is a one stop shop for all of your entertainment and lodging needs nestled in paradise. Book now and reserve the perfect venue!

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

2025 04 - Timeless (179)
Timeless 30A|Easy Beach Access|Private Pool|Outdoor Fireplace|Directly on Lake
Dune Allen Beach
  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
9.8 out of 10, Exceptional, (7 reviews)
Timeless 30A|Easy Beach Access|Private Pool|Outdoor Fireplace|Directly on Lake

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

default

Children

Children allowed: ages 0–17

default

Events

No events allowed

default

Pets

Pets allowed

default

Smoking

Smoking is not permitted

Important information

You need to know

Property # 3777832vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Santa Rosa Beach

Located in Dune Allen Beach, a neighbourhood in Santa Rosa Beach, this holiday home is near theme parks and near the beach. While the natural beauty of Santa Rosa Beach and Miramar Beach can be enjoyed by anyone, those looking for an activity can explore Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links. Sirens at the Beach and Blast Arcade and Laser Maze are also worth visiting. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
View more Holiday homes in Santa Rosa BeachOpens in a new window
Map
Santa Rosa Beach, FL

What's nearby

  • South Walton Beaches - 3 min walk - 0.3 km
  • beach near Dune Allen Regional Beach Access - 5 min walk - 0.4 km
  • Topsail Hill Preserve State Park - 9 min walk - 0.8 km
  • Santa Rosa Beach - 14 min walk - 1.2 km
  • Santa Rosa Beach Golf Club - 3 min drive - 2.1 km

Getting around

  • Fort Walton Beach, FL (VPS-Northwest Florida Regional) - 43 min drive

Restaurants

  • ‪Burger King - ‬7 min drive
  • ‪Santa Rosa Golf & Beach Club - ‬4 min drive
  • ‪Palm Folly Hard Seltzer - ‬8 min drive
  • ‪Stinky's Fish Camp - ‬6 min walk
  • ‪Shunk Gulley Oyster Bar - ‬4 min drive

Frequently asked questions

Is The Road to the Triple Crown - Gulf Views with Large Private Pool Area pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at The Road to the Triple Crown - Gulf Views with Large Private Pool Area?

As of 20 May 2026, prices found for a 1-night stay for 2 adults at The Road to the Triple Crown - Gulf Views with Large Private Pool Area on 1 Aug 2026 start from AU$3,386, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at The Road to the Triple Crown - Gulf Views with Large Private Pool Area?

On-site parking is available at the property.

What time is check-in at The Road to the Triple Crown - Gulf Views with Large Private Pool Area?

Check-in begins at 4:00 PM.

What time is check-out at The Road to the Triple Crown - Gulf Views with Large Private Pool Area?

Checkout is at 10:00 AM.

Where is The Road to the Triple Crown - Gulf Views with Large Private Pool Area located?

Located in Dune Allen Beach, this holiday home is within a 15-minute walk of South Walton Beaches and Santa Rosa Beach. Topsail Hill Preserve State Park and Santa Rosa Beach Golf Club are also within 2 miles (3 km).

Reviews

7.0

Good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 0 out of 2 reviews
Rating 8 - Good. 1 out of 2 reviews
Rating 6 - Okay. 1 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

8.0/10

Cleanliness

8.0/10

Check-in

6.0/10

Communication

8.0/10

Location

8.0/10

Listing accuracy

Reviews

Verified

6/10 Okay

Jon K.

Liked: Check-in, location, listing accuracy
Stayed 7 nights in Jul 2025
Verified

8/10 Good

John B.

Liked: Cleanliness, check-in, location, listing accuracy
Stayed 7 nights in Dec 2024

About the host

Hosted by Five Star Properties and Bliss Beach Rentals

Host profile image

Five Star Properties is more than just a name. We are a provider of premier luxury Destin and 30A Vacation Rentals and first-class service to our guests. Our inventory includes the finest beachfront houses, ocean view houses with a private pool, and oceanfront condos along the Emerald Coast. Our beach houses and condos can be found in the most desired beachside communities such as Holiday Isle, Crystal Beach, Dunes of Destin, 1900 98, Destiny by the Sea, Silver Shells Resort, Gulf Pines, Frangista Beach, Miramar Beach, Sandestin, Dune Allen Beach, Grayton Beach, Seagrove Beach, and WaterColor, FL.

Additionally, we offer a selection of smaller, budget-friendly beach houses and condos in our Bliss Beach Rentals inventory. With Bliss, our focus is providing the same luxury vacation experience and level of service on a smaller scale. With Five Star and Bliss you can find event-friendly, wedding-friendly, and even pet-friendly homes to match any size beach vacation!

As a Vrbo Premier Host, we strive to provide an unmatched level of guest service. Whether you book a 9-bedroom house from Five Star or a 2-bedroom beach condo from Bliss, we guarantee our guests the same luxury vacation experience and hands-on customer service.

Each guest is provided with a welcome gift, and access to exceptional amenities which are unique to each property. Plus,
our Guest Services team is local (located in Miramar Beach, Florida), and can provide a quick response to any question or issue that may arise, any time of day. In addition, we have an in-house maintenance team and cleaning crews who can quickly address any guest emergencies. Our exclusive Guest Portal gives each guest access to all means of communication with our team, as well as an area guide to nearby dining, shopping, services, and attractions. It's no wonder Five Star has been voted Best in Destin two years in a row!

Languages:

English

Premier Host

They consistently provide great experiences for their guests

Tell us how we can improve our siteShare feedback