A wooden pier extending into calm water at sunset.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 ￥23,161
￥61,528 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 ￥9,831
￥23,838 total
includes taxes & fees
Oct 26 - Oct 27
The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking
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.

3. Carrera Cottage ~ Charming 2BR/2BA ~ Walk Downtown

Carrera Cottage ~ Charming 2BR/2BA ~ Walk Downtown
Downtown Historic District
The price is ￥9,994
￥41,735 total
includes taxes & fees
Oct 14 - Oct 15
Carrera Cottage ~ Charming 2BR/2BA ~ Walk Downtown
A covered outdoor seating area with a hot tub, a wooden deck, and a small building with a door and windows.

4. Casita Isabella | Private Hot Tub in the Pines

Casita Isabella | Private Hot Tub in the Pines
St. Augustine
The price is ￥13,135
￥33,561 total
includes taxes & fees
Oct 14 - Oct 15
Casita Isabella | Private Hot Tub in the Pines
A single-story house with a porch, a small garden, and a visible garage door.

5. 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 ￥12,652
￥51,794 total
includes taxes & fees
Oct 19 - Oct 20
Historic St. Aug, Top Rated, Walkable, Rare Free Parking & Pets
A wooden deck with a hot tub, a pool, and outdoor furniture.

6. 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 ￥18,561
￥43,870 total
includes taxes & fees
Nov 3 - Nov 4
Casa Caliente | Plunge Pool, Screened Spa & Two Queen Lofts
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 ￥13,135
￥34,037 total
includes taxes & fees
Oct 14 - Oct 15
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)
The price is ￥16,955
￥38,184 total
includes taxes & fees
Oct 15 - Oct 16
Adorable cottage central to everything
A residential house with a metal roof, surrounded by a white picket fence, palm trees, and a gravel driveway.

9. 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 ￥17,588
￥84,675 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Beach Cottage. Hot Tub. Steps To Beach
A covered porch with wicker furniture, potted plants, and a white railing.

10. 4bed, 2bath on Iconic Magnolia Ave-walking distance to shops and restaurants!

4bed, 2bath on Iconic Magnolia Ave-walking distance to shops and restaurants!
Uptown
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful home in a breathtaking neighberhood, will definitely book again when visiting St Augustines! "
United States
Claudia R.
The price is ￥42,031
￥87,254 total
includes taxes & fees
Nov 2 - Nov 3
4bed, 2bath on Iconic Magnolia Ave-walking distance to shops and restaurants!
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
"Clean and comfortable room. Location is great! I stay here often and it definitely is a good deal for the price. There can be a little noise outside but with the type of hotel it is, it is expected."
Kevin 4-night trip
Posted 13 hours ago
Best Western Seaside Inn

Find out more about Anastasia Island

Anastasia Island Cottages information

Number of reviews
702
Accommodation
44 Cottages
Lowest Price
￥23,838
Highest Price
￥87,254

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