5BR, Pool,HotTub, Putput, Walk to Beach,Game RM! image 1
5BR, Pool,HotTub, Putput, Walk to Beach,Game RM! image 2
Open floor plan
Who knew hanging out in a garage could be so fun!
5BR, Pool,HotTub, Putput, Walk to Beach,Game RM! image 5

5BR, Pool,HotTub, Putput, Walk to Beach,Game RM!

5 bedrooms·3 baths
St. Augustine • Florida
5(38 reviews)

$2,108.99 USD total for 3 nights

Oct 19 – 22, 2026

Multiple King Suites, WALK 2 beach, Dream backyard image 1
Multiple King Suites, WALK 2 beach, Dream backyard image 2
Multiple King Suites, WALK 2 beach, Dream backyard image 3
Multiple King Suites, WALK 2 beach, Dream backyard image 4
Multiple King Suites, WALK 2 beach, Dream backyard image 5

Multiple King Suites, WALK 2 beach, Dream backyard

5 bedrooms·4 baths
St. Augustine • Florida
5(8 reviews)

$2,108.99 USD total for 3 nights

Oct 19 – 22, 2026

12x25' heated, salt water pool with sunledge. We love having the enclosure as we can enjoy it anytime of day with no pesky bugs!
HUGE professional putting green, fully fenced & turfed backyard, hammock, and plenty of games to keep kids and adults alike entertained!
Brand new paver walkway was added in March 2023
Casa del Paraiso - 7BD/5BA Premier Escape!
High end metal artwork is outstanding in this home! We love the open concept living where the kitchen, living area, and dining area all flow together but yet defined enough to create its own space.

Casa del Paraiso - 7BD/5BA Premier Escape!

7 bedrooms·5 baths
St. Augustine • Florida
5(40 reviews)

$3,126.27 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

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

Dining area
Living room
Kitchen
Master bedroom
Outdoor space

Las Olas Cabana - Close to Beach & Restaurants

2 bedrooms·2 baths
St. Augustine • Florida

$467.85 USD total for 3 nights

Oct 19 – 22, 2026

Living room
Master bedroom
Office space
Bedroom 2
Outdoor space

Classy Bohemian Beach Cabana- Close to Beach

2 bedrooms·2 baths
St. Augustine • Florida

$584.40 USD total for 3 nights

Oct 19 – 22, 2026

Living Room
Living Room
Modern dining area filled with natural light and direct access to the fully equipped kitchen. Ideal for shared meals, coffee chats, or cooking together during your beach getaway.
Bedroom 2
Bathroom 1

Lux Beach Cabana - Close to Beach & Restaurants

2 bedrooms·2 baths
St. Augustine • Florida

$560.25 USD total for 3 nights

Oct 19 – 22, 2026

Sunrise at Pier Point image 1
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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

Beach House | Sleeps 14 + Game Room|Steps to Beach image 1
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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

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

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

Family Retreat Near Beach & Historic St. Augustine image 1
Family Retreat Near Beach & Historic St. Augustine image 2
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Family Retreat Near Beach & Historic St. Augustine image 5

Family Retreat Near Beach & Historic St. Augustine

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

$865.00 USD total for 3 nights

Oct 19 – 22, 2026

St. Augustine Vacation Rental | 2BR | 1BA | 1,021 Sq Ft | 3 Steps Required
Covered Deck | Fire Pit | Gas Grill
Tropical Garden | Fenced-In Backyard
Living Room | Smart TV | Free WiFi | Single-Story Home
'Palm Bungalow' Near Dtwn St Augustine & Beaches! image 5

'Palm Bungalow' Near Dtwn St Augustine & Beaches!

3 bedrooms·1 bath
St. Augustine • Florida
4.58(26 reviews)

$733.88 USD total for 3 nights

Mar 25 – 28, 2027

Direct Ocean Access!
Make unforgettable memories. Run down to the beach without ever getting in the car.
The upstairs Main Suite opens up to a private balcony with panoramic Atlantic Ocean views. Blackout curtains, Dechateaux real wood wide plank floors. The other side of the room welcomes you with a spa like bathroom. Two Queen Beds set up like a hotel room.
BeachHouse | 2 Private Decks | Luxury | King Bed
A thoughtfully designed main bath separates the bathing and grooming areas just like a luxury spa. Top of the line Brizo fixtures, Italian tile.

BeachHouse | 2 Private Decks | Luxury | King Bed

3 bedrooms·2 baths
Florida
5(45 reviews)

$2,726.16 USD $2,224.22 USD total for 5 nights

Oct 19 – 24, 2026

Private balcony with ocean views overlooking the pools and direct boardwalk access to beautiful St. Augustine Beach.
Coastal Dreams - Open Concept Living Space Perfect gathering spot for families with natural light and coastal charm
Coastal Dreams - Private Boardwalk to Ocean Walk straight from the gate through the private boardwalk to the beach – just seconds to the sand.
Coastal Dreams - King Primary Bedroom Spacious primary bedroom with comfortable King bed & cable TV and dedicated workspace.
Coastal Dreams - Fully Equipped Kitchen Modern kitchen with PFAS-free cookware and stainless steel appliances.

Coastal Dreams | Renovated Ocean View St Aug Beach

2 bedrooms·2 baths
St. Johns County • Florida
5(29 reviews)

$734.18 USD $623.79 USD total for 3 nights

Oct 19 – 22, 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

View from lanai of intracoastal waterway
Morning sunrise (photo taken from lanai)
View from lanai of intracoastal waterway
22-foot screened in lanai with cafe lights and brand new furniture
22-foot screened in lanai with cafe lights and brand new furniture

Sunrise Paradise on Intracoastal Front

2 bedrooms·2 baths
St. Augustine • Florida
5(12 reviews)

$782.78 USD total for 4 nights

Oct 20 – 24, 2026

Treehouse
Treehouse
Treehouse
Treehouse
Treehouse

Treehouse

2 bedrooms·2 baths
St. Augustine • Florida

$1,271.12 USD $1,215.31 USD total for 7 nights

Mar 31 – Apr 7, 2027

Private walkover from our complex to the beach.
Main living room with 65 inch Flatscreen TV.
Updated Beach Condo - Snowbirds Welcome image 3
Additional seating for 4 at the bar.
Updated Beach Condo - Snowbirds Welcome image 5

Coral Condo at The Ocean Gallery

2 bedrooms·2 baths
St. Augustine • Florida
4.91(11 reviews)

$1,750.00 USD total for 5 nights

Oct 25 – 30, 2026

Quiet Butler Beach Getaway In St. Augustine image 1
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Quiet Butler Beach Getaway In St. Augustine

3 bedrooms·2 baths
St. Augustine • Florida

$1,557.66 USD total for 3 nights

Oct 19 – 22, 2026

The Pelicans Way
The Pelicans Way
The Pelicans Way
The Pelicans Way
The Pelicans Way

The Pelicans Way

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

$721.35 USD total for 3 nights

Oct 19 – 22, 2026

Master suite #1
Vi La Mar
Vi La Mar
Vi La Mar
Relaxing elegant beach house on the beach in South Ponte Vedra Beach is a luxurious retreat designed to provide the ultimate in relaxation and comfort while enjoying the stunning beauty

Vi La Mar

4 bedrooms·4 baths
Ponte Vedra Beach • Florida
5(8 reviews)
$1,200/ night(excl. fees & taxes)