Special offer
Enjoy a night of relaxing in this back yard oasis
New challenging putting green waiting for you
Enjoy evenings at the tiki bar with a tropical vibe
Video games Pac Man and NBA JAM + Board, Card and other games for your indoor fun
Spacious living room with a smart TV for your entertainment.

Spacious 5BR Beach House| Heated Pool, Arcade & Putting Green

5 bedrooms·3½ baths
St. Augustine • Florida

$2,626.32 USD $2,424.85 USD total for 3 nights

Nov 12 – 15, 2026

Featured
Solar-heated saltwater pool for sunny afternoons and evening swims.
Kick back with the Smart TV, games, and comfy seating for all.
Drift off in the king bed after a day at the beach.
Pool table, shuffleboard, and arcade fun all under one roof.
Gather around the fire pit for stories under the stars.

Salty Shores Retreat

3 bedrooms·2 baths
Palm Coast • Florida

$896.99 USD total for 3 nights

Nov 17 – 20, 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

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)

$1,317.22 USD total for 3 nights

Nov 12 – 15, 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

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

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

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(6 reviews)

$879.13 USD total for 3 nights

Nov 20 – 23, 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

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

$1,010.75 USD total for 3 nights

Nov 12 – 15, 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

$680.00 USD total for 3 nights

Nov 12 – 15, 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

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

Private fully fenced yard, hot tub, BBQ and fire pit
4brm- Hot Tub-Firepit-1 mile to Dtwn-Dogs allowed
4brm- Hot Tub-Firepit-1 mile to Dtwn-Dogs allowed
Games for the family
Fully fenced yard with yard games, hot tub, BBQ, outdoor seating and fire pit

4brm- Hot Tub-Firepit-1 mile to Dtwn-Dogs allowed

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

$1,092.46 USD total for 3 nights

Nov 15 – 18, 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

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

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

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

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

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

$1,227.87 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