A wooden pier extending into calm water at sunset.

Search Anastasia Island Cottage Accommodations

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Anastasia Island cottages

1. < 1 Mi to Butler Beach! Group Escape w/ Hot Tub

< 1 Mi to Butler Beach! Group Escape w/ Hot Tub
3.0 star property
Butler Beach
The price is AU$752
includes taxes & fees
22 Nov - 23 Nov
< 1 Mi to Butler Beach! Group Escape w/ Hot Tub

2. Coastal Cottage near Winery

Coastal Cottage near Winery
Oyster Creek
9.8 out of 10, Exceptional, (8 reviews)
"This was the perfect accommodation for a weekend in St. A for four family members. It was well appointed, clean, parking spots for two vehicles and close to the historic district attractions. "
United States
Kristin S.
The price is AU$604
includes taxes & fees
9 Nov - 10 Nov
Coastal Cottage near Winery

3. Casita Isabella | Private Hot Tub in the Pines

Casita Isabella | Private Hot Tub in the Pines
St. Augustine
The price is AU$303
includes taxes & fees
9 Nov - 10 Nov
Casita Isabella | Private Hot Tub in the Pines

4. Adorable cottage central to everything

Adorable cottage central to everything
Ravenswood
10.0 out of 10, Exceptional, (150 reviews)
"Love this place and how close it is to everything!"
United States
David C.
The price is AU$337
includes taxes & fees
9 Nov - 10 Nov
Adorable cottage central to everything

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 AU$490
includes taxes & fees
10 Nov - 11 Nov
Historic St. Aug, Top Rated, Walkable, Rare Free Parking & Pets

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, (4 reviews)
"Perfect for a quiet getaway, the porch with hot tub and tv made it very relaxing."
United States
jeri t.
The price is AU$363
includes taxes & fees
9 Nov - 10 Nov
Casa Caliente | Plunge Pool, Screened Spa & Two Queen Lofts

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 AU$320
includes taxes & fees
12 Nov - 13 Nov
Luxury Tiny Home with Private Hot Tub — 3 Miles to Historic St. Augustine

8. 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, (481 reviews)
"Such a nice little spot."
United States
Miranda
The price is AU$434
includes taxes & fees
30 Nov - 1 Dec
The Red Cottage ~ 5 min. stroll to Historic St. George Street - on site parking

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, (32 reviews)
"Beautiful property!! We will definitely book a stay again in the future."
United States
Michael H.
The price is AU$824
includes taxes & fees
9 Nov - 10 Nov
Cozy Beach Cottage. Hot Tub. Steps To Beach

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

Groveside Cottage in Heart of Town! Park & Walk
Uptown
The price is AU$546
includes taxes & fees
10 Nov - 11 Nov
Groveside Cottage in Heart of Town! Park & Walk

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

Carrera Cottage ~ Charming 2BR/2BA ~ Walk Downtown
Downtown Historic District
The price is AU$704
includes taxes & fees
29 Nov - 30 Nov
Carrera Cottage ~ Charming 2BR/2BA ~ Walk Downtown

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

Immaculate New 2BR/2BA, Hot Tub, Firepit
Vilano Beach
10.0 out of 10, Exceptional, (5 reviews)
"This beautiful home was perfect for our family of three - incredibly clean, feels brand new, with a soothing atmosphere. Ideal for a relaxing beach vacation. The front porch, rear deck and spacious yard provided ample outdoor options and space for children to play. The neighborhood is beautiful and peaceful. Fun restaurants very close by (Aunt Kate’s & Cap’s). Strolling to and from the beach was a joy. Communication with host was outstanding. Thank you for helping us create meaningful memories....
United States
B T.
The price is AU$933
includes taxes & fees
11 Nov - 12 Nov
Immaculate New 2BR/2BA, Hot Tub, Firepit

13. Cottage on Iconic Magnolia Ave-Walk to Attractions!

Cottage on Iconic Magnolia Ave-Walk to Attractions!
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 AU$762
includes taxes & fees
9 Nov - 10 Nov
Cottage on Iconic Magnolia Ave-Walk to Attractions!

14. Historic Dupont Cottages Retreat

Historic Dupont Cottages Retreat
Uptown
The price is AU$2,816
includes taxes & fees
15 Nov - 16 Nov
Historic Dupont Cottages Retreat
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Anastasia Island Hotel Reviews

Find out more about Anastasia Island

Anastasia Island Cottages information

Number of reviews
723
Accommodation
40 Cottages
Lowest Price
AU$303
Highest Price
AU$1,094

Explore a world of travel with Expedia