Overall View of Private Courtyard with Dining Area, Living Area, Fire Table and Fountain all spread throughout a 9 foot walled courtyard with lush plants and interesting decor.
Living Room
Kitchen
Dining & Kitchen
Living

Casa Mahon: Walk to Bridge of Lions & Downtown!

4 bedrooms·2 baths
St. Augustine • Florida
5(49 reviews)

1255,45 $ USD total por 3 noches

26–29 oct 2026

Welcome to Joyful-Stays, Historic St Augustine! Come stay at our home away from home, and walk to the historic sites of Flagler college, Lightner Museum, and St George Street!
This couch is a new queen sleeper sofa, pretty comfortable, if more sleep spaces are needed!
Brand New hot tub for 2-3 people
<10 minutes walk to St George Street.
Enjoy the fully stocked kitchen, with all the conveniences of home including a blender, a coffee station, pots, pans, serveware, and bakeware!

St Augustine.

3 bedrooms·2½ baths
St. Augustine • Florida
5(2 reviews)

791,84 $ USD 757,77 $ USD total por 3 noches

26–29 oct 2026

The Loft in St Augustine FL
Big screen Roku TV
#2 bedroom - Queen
1st bedroom - King
Full sized kitchen

The Loft - Walk to Downtown

2 bedrooms·1 bath
St. Augustine • Florida

778,87 $ USD total por 3 noches

26–29 oct 2026

Nights of lights
Living Room
Kitchen
Exterior
Tesla Wall Connector

Walk to Nights of Lights, trolley #11 + EV charger

2 bedrooms·2 baths
St. Augustine • Florida
5(64 reviews)

523,26 $ USD total por 3 noches

26–29 oct 2026

Retro Oasis Mins to Downtown / Beaches Huge Yard image 1
Retro Oasis Mins to Downtown / Beaches Huge Yard image 3
Retro Oasis Mins to Downtown / Beaches Huge Yard image 4
Retro Oasis Mins to Downtown / Beaches Huge Yard image 5
Retro Oasis Mins to Downtown / Beaches Huge Yard image 2

Retro Oasis Mins to Downtown/Beaches Huge Yard

3 bedrooms·2 baths
St. Augustine • Florida
5(4 reviews)

583,65 $ USD 526,79 $ USD total por 3 noches

26–29 oct 2026

Stylish Historic Retreat|Walk to Downtown|Parking image 1
Stylish Historic Retreat|Walk to Downtown|Parking image 2
Stylish Historic Retreat|Walk to Downtown|Parking image 3
Stylish Historic Retreat|Walk to Downtown|Parking image 4
Stylish Historic Retreat|Walk to Downtown|Parking image 5

Stylish Historic Retreat|Walk to Downtown|Parking

3 bedrooms·3 baths
St. Augustine • Florida
5(7 reviews)
$200 – $395/ noche(sin comisiones ni impuestos)
Bright, cozy living room with sunny windows and a stylish curved sofa.
A welcoming entertainment area centered around a foosball table, encouraging fun, teamwork, and memorable moments.
Master bedroom
Charming St Augustine Oasis/Game Room/Family Fun
Charming St Augustine Oasis/Game Room/Family Fun

Charming St Augustine Oasis/Game Room/Family Fun

3 bedrooms·2 baths
St. Augustine • Florida

606,50 $ USD total por 3 noches

26–29 oct 2026

ST. Sylvan Historic Bungalow
ST. Sylvan Historic Bungalow
ST. Sylvan Historic Bungalow
ST. Sylvan Historic Bungalow
ST. Sylvan Historic Bungalow

ST. Sylvan Historic Bungalow

2 bedrooms·1 bath
St. Augustine • Florida

459,00 $ USD total por 3 noches

26–29 oct 2026

Private fully fenced yard, hot tub, BBQ and fire pit
The Salty Palm- Hot Tub/Fire-pit/ 1 mile to Dwtwn!
The Salty Palm- Hot Tub/Fire-pit/ 1 mile to Dwtwn!
Games for the family
Fully fenced yard with yard games, hot tub, BBQ, outdoor seating and fire pit

The Salty Palm- Hot Tub/Fire-pit/ 1 mile to Dwtwn!

4 bedrooms·2 baths
St. Augustine • Florida
5(76 reviews)

1266,20 $ USD total por 3 noches

29 oct – 1 nov 2026

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

454,00 $ USD total por 3 noches

26–29 oct 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 por 3 noches

1–4 nov 2026

Encanto — A Cheerful Coastal Getaway in Full Bloom
A storybook setting for every meal—sunny, floral, and effortlessly inviting.
Charming Cottage: Bright exterior with vibrant plants and a welcoming turquoise door awaits you!
Morning or night, your grill’s always ready.
Encanto — A Cheerful Coastal Getaway in Full Bloom

Encanto — A Cheerful Coastal Getaway in Full Bloom

3 bedrooms·2 baths
St. Augustine • Florida
5(40 reviews)

781,75 $ USD total por 3 noches

26–29 oct 2026

Welcome! Sunny retreat with a welcoming porch, native plants & coastal charm.
Charming First Impression Casita’s bright exterior, welcoming porch seating, and cheerful landscaping set the tone for a stay filled with warmth, style, and St. Augustine charm from the moment you arrive.
Casita Augustina — A Coastal Cottage with a Hidden Courtyard
Casita Augustina — A Coastal Cottage with a Hidden Courtyard
Waffle Station Delight: Yummy and charming - perfect for a relaxed mornings!

Casita Augustina — A Coastal Cottage with a Hidden Courtyard

3 bedrooms·2 baths
St. Augustine • Florida

747,57 $ USD total por 3 noches

26–29 oct 2026

Serene Swing Under the Oaks Nestled beneath centuries-old oaks draped in Spanish moss, this cozy swing invites you to relax, read, or simply sway with the breeze—a peaceful backyard nook made for slow moments and lasting memories.
Charming First Impression Casita’s bright exterior, welcoming porch seating, and cheerful landscaping set the tone for a stay filled with warmth, style, and St. Augustine charm from the moment you arrive.
Sunshine Duo — Two Coastal Homes Just Down the Road
Two Homes, 1 booking, 0.3 miles apart. Homes for togetherness with privacy!
Cook, dine, and unwind in a fully stocked kitchen designed for effortless meals.

Sunshine Duo — Two Coastal Homes Just Down the Road

6 bedrooms·4 baths
St. Augustine • Florida

1956,19 $ USD total por 3 noches

26–29 oct 2026

La Costa — A Modern Coastal Retreat with a Putting Green
La Costa — A Modern Coastal Retreat with a Putting Green
Views of lush greenery
Modern backyard oasis with putting green, hammock & fenced patio
Private palm-lined yard with putting green, hammock & lounge

La Costa — A Modern Coastal Retreat with a Putting Green

3 bedrooms·2 baths
St. Augustine • Florida

804,05 $ USD total por 3 noches

26–29 oct 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

897,00 $ USD total por 3 noches

26–29 oct 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
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

687,00 $ USD total por 3 noches

26–29 oct 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

992,00 $ USD total por 3 noches

26–29 oct 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
Unwind in your private heated pool, surrounded by a peaceful backyard designed for pure relaxation. Whether it’s a sunny afternoon or an evening swim, this is your personal coastal escape.
Enjoy the spacious open concept dining and living area, thoughtfully designed for hosting meals, connecting with loved ones, and creating lasting vacation memories.
Dining area
Dining area
Bedroom 3

Coastal Cabana - Heated Pool - Walk to Beach

4 bedrooms·3 baths
St. Augustine • Florida

1173,90 $ USD total por 3 noches

26–29 oct 2026

Resort-style splash pad with water jets and shaded pavilion fun
Family Fun Meets Luxury King Suites • Space-Themed Kids’ Room • Designer Kitchen • Near Beaches & Downtown
Resort-style pool with lap lanes, sun deck, and fun waterslide
1 mile from Downtown EV Charger and Pet friendly
Spacious living room designed for together time—gather for games, unwind with a movie on the 65" TV, or settle in on the fold-out couch. Furry companions welcome, with a cozy pet bed included for their comfort.

1 mile from Downtown EV Charger and Pet friendly

3 bedrooms·2 baths
St. Augustine • Florida

815,00 $ USD 738,04 $ USD total por 3 noches

26–29 oct 2026