A wooden pier extending into calm water at sunset.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Anastasia Island cottages

A white house with a garage, surrounded by a garden with various plants and a small patio area.

1. < 1 Mi to Butler Beach! Home w/ Dog-friendly Yard

< 1 Mi to Butler Beach! Home w/ Dog-friendly Yard
3.0 star property
Butler Beach
The price is ￥23,055
￥61,246 total
includes taxes & fees
Oct 25 - Oct 26
< 1 Mi to Butler Beach! Home w/ Dog-friendly Yard
A small red house with a white door, a porch with a striped umbrella, and a mural on the wall.

2. The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking

The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking
Uptown
9.0 out of 10, Wonderful, (478 reviews)
"Highly recommend for 2 people! Perfect location, clean, cute and the host is very attentive!!!! We will be back!!"
United States
Paige F.
The price is ￥9,806
￥23,778 total
includes taxes & fees
Oct 8 - Oct 9
The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking
A covered outdoor seating area with a hot tub, a wooden deck, and a small building with a door and windows.

3. Casita Isabella | Private Hot Tub in the Pines

Casita Isabella | Private Hot Tub in the Pines
St. Augustine
The price is ￥14,528
￥35,028 total
includes taxes & fees
Oct 8 - Oct 9
Casita Isabella | Private Hot Tub in the Pines
A building with a sign for 'Krispy Gallery' and another sign with a clock. There are potted plants outside and a bicycle parked on the sidewalk.

4. Charming 2/2 Cottage ~ Walk to Historic Downtown

Charming 2/2 Cottage ~ Walk to Historic Downtown
Downtown Historic District
The price is ￥14,882
￥47,094 total
includes taxes & fees
Oct 8 - Oct 9
Charming 2/2 Cottage ~ Walk to Historic Downtown
A wooden deck with a hot tub, a pool, and outdoor furniture.

5. Casa Caliente | Plunge Pool, Screened Spa & Two Queen Lofts

Casa Caliente | Plunge Pool, Screened Spa & Two Queen Lofts
St. Augustine
10.0 out of 10, Exceptional, (3 reviews)
"Great listing and a great place for us to get away as a couple! Very clean and the perfect size place. Owner was very nice and just an overall great weekend!"
United States
Jamie H.
The price is ￥18,191
￥43,232 total
includes taxes & fees
Oct 27 - Oct 28
Casa Caliente | Plunge Pool, Screened Spa & Two Queen Lofts
A single-story house with a porch, a small garden, and a visible garage door.

6. Historic St. Aug, Top Rated, Walkable, Rare Free Parking & Pets

Historic St. Aug, Top Rated, Walkable, Rare Free Parking & Pets
Downtown Historic District
10.0 out of 10, Exceptional, (33 reviews)
"Enjoyed our stay - location is excellent to historic district"
United States
Richard W.
The price is ￥14,350
￥53,971 total
includes taxes & fees
Oct 13 - Oct 14
Historic St. Aug, Top Rated, Walkable, Rare Free Parking & Pets
A wooden deck with a hot tub and a sofa with red cushions.

7. Luxury Tiny Home with Private Hot Tub — 3 Miles to Historic St. Augustine

Luxury Tiny Home with Private Hot Tub — 3 Miles to Historic St. Augustine
St. Augustine
8.0 out of 10, Very good, (4 reviews)
"Property was clean and well kept. The amenities were in working order and a nice addition to the experience. Host was very welcoming and quick to respond to any questions or concerns we had. Overall a great experience and would certainly rebook here or one of the adjacent retreats on the property."
United States
Drew R.
The price is ￥14,528
￥35,502 total
includes taxes & fees
Oct 8 - Oct 9
Luxury Tiny Home with Private Hot Tub — 3 Miles to Historic St. Augustine
A modern kitchen with a double sink, a dining area, a gray sofa, and a yellow door.

8. Adorable cottage central to everything

Adorable cottage central to everything
Ravenswood
10.0 out of 10, Exceptional, (147 reviews)
"Great place!! "
United States
Janice H.
The price is ￥15,491
￥36,346 total
includes taxes & fees
Oct 8 - Oct 9
Adorable cottage central to everything
A white two-story house with a porch, stone steps, and a small garden.

9. Groveside Cottage in Heart of Town! Park & Walk

Groveside Cottage in Heart of Town! Park & Walk
Uptown
Groveside Cottage in Heart of Town! Park & Walk
A residential house with a metal roof, surrounded by a white picket fence, palm trees, and a gravel driveway.

10. Cozy Beach Cottage. Hot Tub. Steps To Beach

Cozy Beach Cottage. Hot Tub. Steps To Beach
Vilano Beach
9.8 out of 10, Exceptional, (31 reviews)
"Beautiful property!! We will definitely book a stay again in the future."
United States
Michael H.
The price is ￥17,544
￥84,462 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Beach Cottage. Hot Tub. Steps To Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Anastasia Island Hotel Reviews

Best Western Seaside Inn

Best Western Seaside Inn

10/10 Excellent
"Great Hotel in St Augustine Beach , not far from St Augustine Pier. Great breakfast and coffee . Rooms in excellent condition."
Thomas 1-night trip
Posted 7 hours ago
Best Western Seaside Inn

Find out more about Anastasia Island

Anastasia Island Cottages information

Number of reviews
696
Accommodation
44 Cottages
Lowest Price
￥23,778
Highest Price
￥84,462

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