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

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

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

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

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

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

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
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

$1,044.24 USD $895.77 USD total for 3 nights

May 1 – 4, 2027

Living room with vaulted ceiling, arcade game, open floor plan
Living room with Smart TV with streaming, Xbox 1S with games and Blu-ray, electric fireplace, power reclining couches, lift-up coffee table, and full-size head-to-head Arcade game with Ms. Pacman and 10 other games.
Comfortable King size bed, with a twin trundle underneath. His/Her closets, ensuite bathroom with tile shower and double sinks. Smart TV with dresser. Touch lamps with wireless phone charging.
Seating for 6 at the table.
West Oasis #1

West Oasis #1

3 bedrooms·2 baths
St. Augustine • Florida

$566.19 USD $552.94 USD total for 3 nights

Nov 15 – 18, 2026

West Oasis #2
Full-size arcade game. Coffee table lifts up and has games inside
Backyard has a built-in firepit with 4 adirondak chairs, a picnic table and propane grill with propane provided
Single Level Home
Seating for 6 at the dining room table

West Oasis #2

3 bedrooms·2 baths
St. Augustine • Florida

$562.42 USD $549.27 USD total for 3 nights

Nov 15 – 18, 2026