Location

Dates

Guests

Vacation rentals in St. Augustine

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

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

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

$2,191.35 USD total for 3 nights

Nov 12 – 15, 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

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

May 1 – 4, 2027

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

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

3 bedrooms·2 baths

St. Augustine • Florida

$566.19 USD $552.94 USD total for 3 nights

Nov 15 – 18, 2026

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

West Oasis #5

3 bedrooms·2 baths

St. Augustine • Florida

$517.11 USD $505.35 USD total for 3 nights

Nov 16 – 19, 2026

Comfortable reclining sofas, full-size Pacman arcade game (with Galaga and many other games) coffee table lifts up, board games in table.

Step inside to an open concept house with large dining table and large couches so everyone can gather together.

Outdoor area has a stone patio, stone fire pit, 4 adirondak-style chairs, and an 8-seat picnic table, with a fully fenced, private backyard.

Primary Bedroom has a King size bed, ensuite bathroom with walk-in shower and double vanity, dresser with smart TV on top, lighted mirror, pack n play and air mattress always available inside the closet.

West Oasis #6

3 bedrooms·2 baths

St. Augustine • Florida

$513.34 USD $501.68 USD total for 3 nights

Nov 17 – 20, 2026

West Oasis 5 & 6 Combined

Comfortable reclining sofas, full-size Pacman arcade game (with Galaga and many other games) coffee table lifts up, board games in table.

Primary Bedroom has a King size bed, ensuite bathroom with walk-in shower and double vanity, dresser with smart TV on top, lighted mirror, pack n play and air mattress always available inside the closet.

Primary bathroom has double vanity, large walk-in shower, body wash, shampoo, conditioner, plenty of towels, hair dryer, and first aid kit

West Oasis 5 & 6 Combined

6 bedrooms·4 baths

St. Augustine • Florida

$1,560.17 USD $1,520.76 USD total for 3 nights

Nov 29 – Dec 2, 2026

Power Recliners, Smart TV, Xbox one with games, Arcade Machine, board games

Power Recliners, Smart TV, Xbox one with games, Arcade Machine, board games

Full kitchen with refrigerator with water and ice dispenser, stove, oven, keurig with pods, hot water heater, toaster, pots/pans, baking sheets, cooking utensils, mixing bowls, plateware for 12, kids plateware, cups, wine glasses, coffee mugs, + more

Master bedroom with King Bed, twin trundle pull-out under King Bed, Smart TV, dresser, 2x closets, pack n' play in closet, ensuite bathroom

West Oasis #3

3 bedrooms·2 baths

St. Augustine • Florida

$558.65 USD $545.62 USD total for 3 nights

Nov 15 – 18, 2026

Reclining sofas, Smart TV, electric fireplace, games, lifting coffee table

Coffee mugs with Keurig coffee maker (pods included), hot water heater, mini waffle maker, blender, stove, oven, dishwasher, fridge, filtered water, knives, cutting board, pots/pans, baking sheets, utensils.

Open concept with Dining Table for 6, dishware for 10+ to include children's dishware, fully stocked kitchen, comfy reclining sofas, full-size arcade system, Smart TV, and Xbox

Primary Bedroom has King Bed with Twin Trundle underneath, pack n' play in closet, full en-suite bathroom, 2 closets, Smart TV

Outdoor firepit with 4 Adirondack chairs, BBQ grill, and outdoor picnic table

West Oasis #4

3 bedrooms·2 baths

St. Augustine • Florida

$554.86 USD $541.96 USD total for 3 nights

Nov 15 – 18, 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

$1,073.24 USD $1,048.45 USD total for 3 nights

Nov 15 – 18, 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 total for 3 nights

Nov 15 – 18, 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 total for 3 nights

Nov 15 – 18, 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

$820.59 USD $762.72 USD total for 3 nights

Nov 13 – 16, 2026

Pool~4 bdr~Game Room~Close2Downtown~Pet-Friendly

Pool~4 bdr~Game Room~Close2Downtown~Pet-Friendly

Pool~4 bdr~Game Room~Close2Downtown~Pet-Friendly

Pool~4 bdr~Game Room~Close2Downtown~Pet-Friendly

Pool~4 bdr~Game Room~Close2Downtown~Pet-Friendly

Pool~4 bdr~Game Room~Close2Downtown~Pet-Friendly

4 bedrooms·2 baths

St. Augustine • Florida

4.93(28 reviews)

$1,556.00 USD total for 4 nights

Nov 12 – 16, 2026

Secluded Cottage walk to Amphitheater/near the beach and downtown

Secluded Cottage walk to Amphitheater/near the beach and downtown

Secluded Cottage walk to Amphitheater/near the beach and downtown

Entrance to back yard

Secluded Cottage walk to Amphitheater/near the beach and downtown

1 bedroom·1 bath

St. Augustine • Florida

$420.54 USD total for 3 nights

Nov 14 – 17, 2026

Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

Midcentury Bungalow w/hot tub, near the amphitheater/beach/downtown

3 bedrooms·2 baths

St. Augustine • Florida

$665.61 USD total for 3 nights

Nov 15 – 18, 2026

Madeira apartment-walkable to amphitheater and more

Madeira apartment-walkable to amphitheater and more

Madeira apartment-walkable to amphitheater and more

Madeira apartment-walkable to amphitheater and more

1 bedroom·1 bath

St. Augustine • Florida

$346.76 USD total for 3 nights

Nov 15 – 18, 2026

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

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

3 bedrooms·2 baths

St. Augustine • Florida

$717.17 USD $699.40 USD total for 3 nights

Nov 12 – 15, 2026