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Vacation rentals in St. Augustine

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 for 3 nights

Oct 19 – 22, 2026

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.

Dining & Kitchen

Casa Mahon: Walk to Bridge of Lions & Downtown!

4 bedrooms·2 baths

St. Augustine • Florida

5(49 reviews)

$1,255.45 USD total for 3 nights

Oct 19 – 22, 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!

<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)

$794.08 USD $759.87 USD total for 3 nights

Oct 19 – 22, 2026

Nights of lights

Tesla Wall Connector

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

2 bedrooms·2 baths

St. Augustine • Florida

5(64 reviews)

$541.45 USD total for 3 nights

Oct 19 – 22, 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 for 3 nights

Oct 19 – 22, 2026

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.

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

$580.25 USD total for 3 nights

Oct 19 – 22, 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

$444.00 USD total for 3 nights

Oct 19 – 22, 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(59 reviews)

$1,096.31 USD $966.59 USD total for 3 nights

Oct 19 – 22, 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

$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

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)

$1,002.77 USD total for 3 nights

Oct 23 – 26, 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

$753.26 USD total for 3 nights

Oct 19 – 22, 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

$2,411.91 USD total for 3 nights

Oct 23 – 26, 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 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

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

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

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.

Coastal Cabana - Heated Pool - Walk to Beach

4 bedrooms·3 baths

St. Augustine • Florida

$1,939.35 USD total for 3 nights

Oct 23 – 26, 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

$864.89 USD $780.45 USD total for 3 nights

Oct 19 – 22, 2026

Flooded with natural light, this open concept living and dining space is perfect for relaxing, sharing meals, and enjoying the clean modern coastal vibe.

Luxury Modern Comfort in Historic St Augustine

Luxury Modern Comfort in Historic St Augustine

Luxury Modern Comfort in Historic St Augustine

Luxury Modern Comfort in Historic St Augustine

Luxury Modern Comfort in Historic St Augustine

3 bedrooms·2 baths

St. Augustine • Florida

$625.40 USD total for 3 nights

Oct 19 – 22, 2026