A wooden pier extending into calm water at sunset.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Anastasia Island cottages

A small red house with a white door, a porch with a striped umbrella, and a mural on the wall.

1. 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
9.2 out of 10, Wonderful, (477 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 ￥9,778
￥23,709 total
includes taxes & fees
Sep 24 - Sep 25
The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking
A modern kitchen with a double sink, a dining area, a gray sofa, and a yellow door.

2. Adorable cottage central to everything

Adorable cottage central to everything
Ravenswood
10.0 out of 10, Exceptional, (144 reviews)
"Great place!! "
United States
Janice H.
The price is ￥18,280
￥39,873 total
includes taxes & fees
Sep 24 - Sep 25
Adorable cottage central to everything
A wooden deck with a hot tub, a pool, and outdoor furniture.

3. 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, (2 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 ￥16,296
￥40,857 total
includes taxes & fees
Sep 24 - Sep 25
Casa Caliente | Plunge Pool, Screened Spa & Two Queen Lofts
A residential house with a metal roof, surrounded by a white picket fence, palm trees, and a gravel driveway.

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

Cozy Beach Cottage. Hot Tub. Steps To Beach
Vilano Beach
9.8 out of 10, Exceptional, (30 reviews)
"Beautiful property!! We will definitely book a stay again in the future."
United States
Michael H.
The price is ￥16,107
￥82,027 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Beach Cottage. Hot Tub. Steps To Beach
A backyard with a fire pit, a covered seating area, and a small building.

5. 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 ￥13,037
￥33,625 total
includes taxes & fees
Sep 24 - Sep 25
Luxury Tiny Home with Private Hot Tub — 3 Miles to Historic St. Augustine
A hot tub on a wooden deck with a wicker chair and a small table, surrounded by greenery.

6. Casita Isabella | Private Hot Tub in the Pines

Casita Isabella | Private Hot Tub in the Pines
St. Augustine
The price is ￥13,037
￥33,625 total
includes taxes & fees
Sep 24 - Sep 25
Casita Isabella | Private Hot Tub in the Pines
A two-story house with a front porch, a garage, and a garden with various plants.

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

Charming 2/2 Cottage ~ Walk to Historic Downtown
Downtown Historic District
The price is ￥19,343
￥52,242 total
includes taxes & fees
Sep 30 - Oct 1
Charming 2/2 Cottage ~ Walk to Historic Downtown
A house with a porch, a bench, and a gravel driveway.

8. Short driving distance from St. George's shopping and the serene Vilano Beach

Short driving distance from St. George's shopping and the serene Vilano Beach
Greater Fullerwood
9.8 out of 10, Exceptional, (12 reviews)
"Charming place with a good blend of"
United States
Matthew
The price is ￥14,673
￥36,422 total
includes taxes & fees
Sep 27 - Sep 28
Short driving distance from St. George's shopping and the serene Vilano Beach
A hot tub in a covered outdoor area with a wooden deck and green chairs.

9. Immaculate New 2BR/2BA, Hot Tub, Firepit

Immaculate New 2BR/2BA, Hot Tub, Firepit
Vilano Beach
10.0 out of 10, Exceptional, (4 reviews)
"Your place was perfect for our long weekend getaway, and we particularly enjoyed playing cornhole in the backyard. I highly recommend "
United States
Alicia J.
The price is ￥18,359
￥85,127 total
includes taxes & fees
Sep 29 - Sep 30
Immaculate New 2BR/2BA, Hot Tub, Firepit
A white two-story house with a porch, stone steps, and a small garden.

10. 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 covered outdoor seating area with a glass table, two chairs with cushions, and potted plants.

11. 4 Bedroom Beach Bliss

4 Bedroom Beach Bliss
3.0 star property
Palm Coast
The price is ￥168,425
￥471,854 total
includes taxes & fees
Oct 1 - Oct 2
4 Bedroom Beach Bliss
A single-story house with a porch, a small garden, and a visible garage door.

12. 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 ￥11,223
￥49,838 total
includes taxes & fees
Sep 29 - Sep 30
Historic St. Aug, Top Rated, Walkable, Rare Free Parking & Pets
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
"Excellent stay. Room was very clean and looked out towards the ocean. Breakfast was excellent and had a rotating menu. Parking was free and very close. Loved the staff! Very helpful and knowledgeable about the area. We had a great time!"
Johnny 2-night trip
Posted 1 hour ago
Best Western Seaside Inn

Find out more about Anastasia Island

Anastasia Island Cottages information

Number of reviews
229
Accommodation
44 Cottages
Lowest Price
￥33,625
Highest Price
￥471,854

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