St Augustine whole house w/ hot tub near downtown
St Augustine whole house w/ hot tub near downtown
St Augustine whole house w/ hot tub near downtown
St Augustine whole house w/ hot tub near downtown
St Augustine whole house w/ hot tub near downtown

St Augustine whole house w/ hot tub near downtown

5 bedrooms·4 baths
St. Augustine • Florida

$1,718.10 USD total for 3 nights

Nov 15 – 18, 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

$1,496.00 USD total for 3 nights

Nov 12 – 15, 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

$1,170.00 USD total for 3 nights

Nov 12 – 15, 2026

Tropical vibes at The Tipsy Tiki For safety reasons, we do not provide pool floats—guests are welcome to bring their own.
Tipsy Tiki – Private Pool, Pet-Friendly, Near Beaches & Downtown
Tipsy Tiki – Private Pool, Pet-Friendly, Near Beaches & Downtown
Private tropical pool oasis with lush landscaping and sunny lounge space
Tipsy Tiki – Private Pool, Pet-Friendly, Near Beaches & Downtown

Tipsy Tiki – Private Pool, Pet-Friendly, Near Beaches & Downtown

5 bedrooms·2 baths
St. Augustine • Florida

$1,488.50 USD total for 3 nights

Nov 12 – 15, 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

$1,349.00 USD total for 3 nights

Nov 12 – 15, 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
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

Nov 16 – 19, 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

$806.00 USD total for 3 nights

Nov 12 – 15, 2026

Welcome, we would love to host your stay!
Relax, refresh, unwind
It's easy to make yourself at home here at The South Street House
Unique charm at each turn
Spacious king suite, balcony with lake view and ambient lighting, day or night

The South Street House

4 bedrooms·4½ baths
St. Augustine • Florida

$8,809.20 USD total for 4 nights

Nov 12 – 16, 2026

It's easy to make yourself at home here at The South Street House
Well equipped chefs kitchen, plenty of space to gather with friends
Spacious king suite, balcony with lake view and ambient lighting, day or night
Relax, refresh, unwind
Welcome, we would love to host your stay!

The South Street House 3

3 bedrooms·3½ baths
St. Augustine • Florida

$5,284.30 USD total for 4 nights

Nov 12 – 16, 2026

St. George Cottage House
St. George Cottage House
St. George Cottage House
St. George Cottage House
St. George Cottage House

St. George Cottage House

3 bedrooms·2 baths
St. Augustine • Florida

$22,330.42 USD total for 30 nights

Nov 12 – Dec 12, 2026

Coastal Cottage -firepit, pet fence, kayaks, bikes image 1
This elegant traditional coastal cottage living room is such a lovely space to relax while on vacation to St. Augustine, Florida.
Welcome to The Inlet Cottage! A peaceful retreat by the inlet off the ocean, strolling distance from the lighthouse.
Coastal Cottage -firepit, pet fence, kayaks, bikes image 4
This cute coastal cottage is a lovely reminder of "Olde Florida" aesthetics.

Coastal Cottage -firepit, pet fence, kayaks, bikes

2 bedrooms·1 bath
St. Augustine • Florida
4.91(240 reviews)

$790.00 USD total for 3 nights

Nov 12 – 15, 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)

$1,300.00 USD total for 3 nights

Nov 12 – 15, 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)

$697.26 USD total for 3 nights

Nov 17 – 20, 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

$980.30 USD total for 3 nights

Nov 12 – 15, 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

$813.47 USD total for 3 nights

Nov 14 – 17, 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)

$1,373.12 USD $1,338.65 USD total for 3 nights

Dec 13 – 16, 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)

$1,178.23 USD total for 3 nights

Nov 12 – 15, 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

$2,615.84 USD total for 3 nights

Nov 12 – 15, 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

$1,137.22 USD total for 3 nights

Nov 12 – 15, 2026

tunning large calico shell art & vibrant colors create a lively ambiance. Cozy seating for four under a beautiful rattan chandelier ensures stylish, inviting meals.
Spacious kitchen, fully stocked for culinary adventures! Enjoy multiple coffee options (drip, Keurig, coffee pot) & island seating for four. Perfect for cooking, entertaining & morning brews.
Our large, spacious wraparound deck boasts outdoor seating for 8, loungers, deck chairs & umbrellas. Grill up your favorites on the charcoal camp grill! Plus, an outdoor shower to rinse off after beach days. Perfect for relaxation & entertaining.
5-Min Beach Walk • Big Deck • 3BR • Outdoor Shower image 4
5-Min Beach Walk • Big Deck • 3BR • Outdoor Shower image 5

5-Min Beach Walk • Big Deck • 3BR • Outdoor Shower

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

$1,195.00 USD total for 3 nights

Nov 12 – 15, 2026