Private gated walkway to the beach
Private walkway to beach
Sea Winds 18 Entry
Welcome / Front door
Entryway

Townhouse steps from the sand

2 bedrooms·2½ baths
St. Augustine Beach • Florida

$1,137.30 USD total for 3 nights

Oct 26 – 29, 2026

Updated Oceanfront Townhome-20% New Owner Special!
Updated Oceanfront Townhome-20% New Owner Special!
Updated Oceanfront Townhome-20% New Owner Special!
Updated Oceanfront Townhome-20% New Owner Special!
Updated Oceanfront Townhome-20% New Owner Special!

Updated Oceanfront Townhome-20% New Owner Special!

2 bedrooms·2 baths
St. Augustine • Florida

$1,281.00 USD total for 3 nights

Oct 26 – 29, 2026

Living room/dining room
Downtown with Christmas lights (last until Jan 31, 2022)
Bumper pool table
Key hanger next to front door
Living room

Wildwood Retreat -near the Beach&Historic Downtown

3 bedrooms·2 baths
St. Augustine • Florida
5(97 reviews)

$664.65 USD total for 3 nights

Oct 31 – Nov 3, 2026

Beach House | Sleeps 14 + Game Room|Steps to Beach image 1
Beach House | Sleeps 14 + Game Room|Steps to Beach image 2
Beach House | Sleeps 14 + Game Room|Steps to Beach image 3
Beach House | Sleeps 14 + Game Room|Steps to Beach image 4
Beach House | Sleeps 14 + Game Room|Steps to Beach image 5

Beach House | Sleeps 14 + Game Room|Steps to Beach

4 bedrooms·3 baths
St. Augustine • Florida
5(4 reviews)

$2,200.00 USD total for 3 nights

Oct 19 – 22, 2026

BigFams/BBQ/Bikes/55 Min>JAX/5 Min>Beach+StatePark
BigFams/BBQ/Bikes/55 Min>JAX/5 Min>Beach+StatePark
BigFams/BBQ/Bikes/55 Min>JAX/5 Min>Beach+StatePark
Travel light with the whole family! We provide a clean, supportive infant bath tub (conveniently stored in the downstairs primary bedroom closet) so you can easily manage bedtime routines during your stay
BigFams/BBQ/Bikes/55 Min>JAX/5 Min>Beach+StatePark

BigFams/BBQ/Bikes/55 Min>JAX/5 Min>Beach+StatePark

3 bedrooms·2½ baths
St. Augustine • Florida
$208/ night(excl. fees & taxes)
An open-concept layout that makes it easy to entertain and spend quality time together
Trade the daily grind for coastal vibes. Nestled beneath a canopy of majestic oak and palm trees, Coastal Soul Beach House offers the ultimate blend of luxury, privacy, and relaxation
Need to take a quick meeting or catch up on emails? This spacious upstairs bedroom features a dedicated office desk and ergonomic chair, making remote work a breeze
Just minutes from your front door! Spend your days exploring the soft sands, searching for seashells, and walking along the beautiful local pier.
Skip the car keys and cruise the local paths. We provide bikes for your stay (conveniently tucked away in the garage when not in use) so you can easily ride to local shops, dining, or the beach.

Cozy St. Augustine Beach Retreat Near Historic DT

3 bedrooms·2½ baths
St. Augustine • Florida

$576.00 USD total for 3 nights

Oct 19 – 22, 2026

Sunrise at Pier Point image 1
Sunrise at Pier Point image 2
Sunrise at Pier Point image 3
Sunrise at Pier Point image 4
Sunrise at Pier Point image 5

Sunrise at Pier Point

2 bedrooms·2 baths
St. Augustine • Florida
5(1 review)

$819.00 USD total for 3 nights

Oct 19 – 22, 2026

Welcome to The Sand Bucket at Seaside at Anastasia!
Come on in and have a look around.
Granite countertops and stainless appliances - fully equipped kitchen.
55” Smart Tv to enjoy from living and dining area
Dining area

The Sand Bucket at Seaside at Anastasia

3 bedrooms·2 baths
St. Augustine Beach • Florida
5(91 reviews)

$1,747.38 USD total for 5 nights

Oct 19 – 24, 2026

The Mermaid House Pet Friendly
The Mermaid House Pet Friendly
Welcome Home
The Mermaid House Pet Friendly
The Mermaid House Pet Friendly

The Mermaid House Pet Friendly

2 bedrooms·1 bath
Ormond Beach • Florida
5(17 reviews)

$1,137.50 USD total for 4 nights

Oct 19 – 23, 2026

King sized bed and recliner in bedroom with nightstands, dresser, 55" Smart TV and desk. Ensuite bathroom and walk in closet.
Living Room with 50" Smart TV with cable, internet and fireplace. Queen sized sleeper sofa with easy to move coffee table on casters.
Enclosed balcony with river and amazing sunset views of the Halifax River and Tomoka State Park. Ocean views can be enjoyed across the hall in the owners' lounge from 8:00 am to 10:00 pm daily.
Steps to the coral colored sand and ocean. Lifeguard stand is only a few yards away.
Open concept condo allows for different areas to cook, eat and relax while still being together.

TopFLR-Oceanfront Bldg, Pool, Parking Views & Gear

1 bedroom·1 bath
Ormond Beach • Florida

$751.73 USD total for 4 nights

Oct 19 – 23, 2026

The Gecko House(Pet Friendly )
The Gecko House(Pet Friendly )
Under cover dining table for 8
Gas firepit area
The Gecko House(Pet Friendly )

The Gecko House(Pet Friendly )

3 bedrooms·1½ baths
Ormond Beach • Florida
4.93(42 reviews)

$1,828.13 USD total for 4 nights

Oct 19 – 23, 2026

Secluded Cottage walk to Amphitheater/near the beach and downtown
Secluded Cottage walk to Amphitheater/near the beach and downtown
Secluded Cottage walk to Amphitheater/near the beach and downtown
House
Entrance to back yard

Secluded Cottage walk to Amphitheater/near the beach and downtown

1 bedroom·1 bath
St. Augustine • Florida

$389.84 USD total for 3 nights

Nov 1 – 4, 2026

Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown
Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown
Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown
Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown
Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

3 bedrooms·2 baths
St. Augustine • Florida

$644.58 USD total for 3 nights

Oct 25 – 28, 2026

Madeira apartment-walkable to amphitheater and more
Madeira apartment-walkable to amphitheater and more
Madeira apartment-walkable to amphitheater and more
entrance
street view

Madeira apartment-walkable to amphitheater and more

1 bedroom·1 bath
St. Augustine • Florida

$349.16 USD total for 3 nights

Oct 25 – 28, 2026

Charming entrance with vibrant landscaping
Serene deck surrounded by lush greenery
Cozy living room with natural light
Relaxing hot tub in a lush garden
Lush garden path to your retreat

St Augustine whole house w/ hot tub near downtown

5 bedrooms·4 baths
St. Augustine • Florida

$1,720.91 USD total for 3 nights

Nov 1 – 4, 2026

The Look-Out - Holiday Home
The Look-Out - Holiday Home
The Look-Out - Holiday Home
The Look-Out - Holiday Home
The Look-Out - Holiday Home

The Look-Out - Holiday Home

5 bedrooms·4 baths
St. Augustine • Florida

$1,064.00 USD total for 3 nights

Oct 19 – 22, 2026

Anastasia Island Villa Duplex| Single Level | EV
Anastasia Island Villa Duplex| Single Level | EV
Anastasia Island Villa Duplex| Single Level | EV
Anastasia Island Villa Duplex| Single Level | EV
Anastasia Island Villa Duplex| Single Level | EV

Anastasia Island Villa Duplex| Single Level | EV

3 bedrooms·2 baths
St. Augustine • Florida
Free EV Charging | Upper Level + Private Rooftop
Free EV Charging | Upper Level + Private Rooftop
Free EV Charging | Upper Level + Private Rooftop
Free EV Charging | Upper Level + Private Rooftop
Free EV Charging | Upper Level + Private Rooftop

Free EV Charging | Upper Level + Private Rooftop

2 bedrooms·2 baths
St. Augustine • Florida
Oasis Over the Bridge of Lions
Oasis Over the Bridge of Lions
Oasis Over the Bridge of Lions
Oasis Over the Bridge of Lions
Oasis Over the Bridge of Lions

Oasis Over the Bridge of Lions

4 bedrooms·3 baths
St. Augustine • Florida

$744.00 USD total for 3 nights

Oct 19 – 22, 2026

Two House Island Retreat
Two House Island Retreat
Two House Island Retreat
Two House Island Retreat
Two House Island Retreat

Two House Island Retreat

5 bedrooms·3 baths
St. Augustine • Florida

$961.00 USD total for 3 nights

Oct 19 – 22, 2026

Anastasia Island Retreat
Anastasia Island Retreat
Anastasia Island Retreat
Anastasia Island Retreat
Anastasia Island Retreat

Anastasia Island Retreat

3 bedrooms·2 baths
St. Augustine • Florida
Anastasia Island Treehouse
Anastasia Island Treehouse
Anastasia Island Treehouse
Anastasia Island Treehouse
Anastasia Island Treehouse

Anastasia Island Treehouse

2 bedrooms·1 bath
St. Augustine • Florida
Sunset deck with fire pit, lantern lighting, and cozy Adirondack seating
Bright modern dining space with stylish seating and natural light
Bright open-plan kitchen and lounge with island seating and modern style
Charming home with curved driveway, lush yard, and glowing sunset curb appeal
Cozy backyard deck with sunset views, outdoor seating, and shady trees

Downtown Bungalow — Walk to Bars, Near Beach

2 bedrooms·1 bath
St. Augustine • Florida

$501.00 USD total for 3 nights

Oct 19 – 22, 2026

The Anastasia House St Augustine Vacation Rental
The Anastasia House St Augustine Vacation Rental
The Anastasia House St Augustine Vacation Rental
The Anastasia House St Augustine Vacation Rental
The Anastasia House St Augustine Vacation Rental

The Anastasia House St Augustine Vacation Rental

2 bedrooms·2 baths
St. Augustine • Florida
4.91(218 reviews)

$711.54 USD total for 3 nights

Oct 19 – 22, 2026