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
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

$ 584,00 USD totaal voor 3 nachten

15–18 nov 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 totaal voor 3 nachten

16–19 nov 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

$ 8.504,80 USD totaal voor 4 nachten

15–19 nov 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

$ 5.113,84 USD totaal voor 4 nachten

15–19 nov 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

$ 22.315,80 USD totaal voor 30 nachten

15 nov – 15 dec 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

$ 757,70 USD totaal voor 3 nachten

15–18 nov 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)

$ 1.470,00 USD totaal voor 3 nachten

15–18 nov 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)

$ 900,00 USD totaal voor 3 nachten

29 nov – 2 dec 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)

$ 682,48 USD totaal voor 3 nachten

17–20 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)

$ 892,25 USD totaal voor 3 nachten

15–18 nov 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)

$ 1.751,68 USD $ 1.705,85 USD totaal voor 3 nachten

20–23 nov 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 totaal voor 3 nachten

15–18 nov 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

$ 2.153,29 USD totaal voor 3 nachten

15–18 nov 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

$ 878,59 USD totaal voor 3 nachten

15–18 nov 2026

Relax in this welcoming living space with a soft sofa, two stylish sitting chairs, and a smart TV for movie nights. The room flows directly into the dining room, making it perfect for family time.
Cozy pergola patio with fire table, string lights, and stylish outdoor seating
Charming lit patio with grill, dining space, and private fenced yard
Prime St. Augustine location near beaches and historic downtown
Retro Ms. Pac-Man arcade cabinet with matching stool for nostalgic fun

Near Downtown+Backyard Oasis+Fire Pit

2 bedrooms·2 baths
St. Augustine • Florida

$ 671,45 USD $ 628,50 USD totaal voor 3 nachten

15–18 nov 2026

2 Homes Near Nights of Lights St Augustine
Cozy pergola patio with fire table, string lights, and stylish seating
Centrally located St. Augustine stay near beaches, downtown, and top sights
Cozy fenced patio with string lights, grill, and outdoor dining
Colorful splash pad with water jets and shaded pavilion fun

2 Homes Near Nights of Lights St Augustine

5 bedrooms·4 baths
St. Augustine • Florida
$455 – $2.005/ nacht(excl. kosten & belastingen)
Prime St. Augustine location near beaches, downtown, and top attractions
Resort-style pool with lap lanes and a fun family splash zone
Near downtown St Augustine Pet friendly
Colorful splash pad with shaded pavilion for family-friendly outdoor fun
Near downtown St Augustine Pet friendly

Near downtown St Augustine Pet friendly

3 bedrooms·2 baths
St. Augustine • Florida

$ 867,15 USD totaal voor 3 nachten

29 nov – 2 dec 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

$ 931,65 USD totaal voor 3 nachten

15–18 nov 2026

Collie Cottage
Livingroom with power recliner couch (head and footrest), expanding table, and reclining leather chairs.
Large kitchen and fridge
Master bedroom with King Bed
Collie Cottage

Collie Cottage

3 bedrooms·2 baths
St. Augustine • Florida

$ 535,99 USD $ 523,65 USD totaal voor 3 nachten

15–18 nov 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)

$ 1.135,00 USD totaal voor 3 nachten

15–18 nov 2026

West Oasis 1 & 2 Combined
West Oasis 1 & 2 Combined
West Oasis 1 & 2 Combined
West Oasis 1 & 2 Combined
West Oasis 1 & 2 Combined

West Oasis 1 & 2 Combined

6 bedrooms·4 baths
St. Augustine • Florida

$ 997,75 USD $ 975,21 USD totaal voor 3 nachten

15–18 nov 2026

West Oasis 1 & 2 & 3 & 4 Combined
West Oasis 1 & 2 & 3 & 4 Combined
West Oasis 1 & 2 & 3 & 4 Combined
West Oasis 1 & 2 & 3 & 4 Combined
West Oasis 1 & 2 & 3 & 4 Combined

West Oasis 1 & 2 & 3 & 4 Combined

12 bedrooms·8 baths
St. Augustine • Florida

$ 1.908,69 USD $ 1.865,78 USD totaal voor 3 nachten

15–18 nov 2026

West Oasis 1 & 2 & 3 Combined
Oasis 1(Blue), Oasis 2(Yellow), Oasis 3 (Green)
West Oasis 1 & 2 & 3 Combined
West Oasis 1 & 2 & 3 Combined
West Oasis 1 & 2 & 3 Combined

West Oasis 1 & 2 & 3 Combined

9 bedrooms·6 baths
St. Augustine • Florida

$ 1.493,49 USD $ 1.459,62 USD totaal voor 3 nachten

15–18 nov 2026