Anastasia Island Cottages ￥14,693

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Our top choices for Anastasia Island cottages

A covered outdoor deck with wicker furniture, a ceiling fan, and string lights.

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

Butler Beach

￥82,420 total

includes taxes & fees

Nov 22 - Nov 23

A covered outdoor seating area with a hot tub, a wooden deck, and a small building with a door and windows.

2. Casita Isabella | Private Hot Tub in the Pines

St. Augustine

A two-story house with a front porch, a red door, and a white picket fence.

3. Coastal Cottage near Winery

Oyster Creek

Kristin S.

A wooden deck with a hot tub, a pool, and outdoor furniture.

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

St. Augustine

jeri t.

￥41,894 total

includes taxes & fees

Nov 17 - Nov 18

A two-story house with a covered porch, a fenced yard, and a well-maintained lawn.

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

Downtown Historic District

Richard W.

￥69,884 total

includes taxes & fees

Nov 23 - Nov 24

A modern kitchen with a double sink, a dining area, a gray sofa, and a yellow door.

6. Adorable cottage central to everything

Ravenswood

David C.

￥40,425 total

includes taxes & fees

Nov 17 - Nov 18

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

St. Augustine

Drew R.

￥34,468 total

includes taxes & fees

Nov 18 - Nov 19

A residential house with a metal roof, surrounded by a white picket fence, palm trees, and a gravel driveway.

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

Vilano Beach

Michael H.

￥95,754 total

includes taxes & fees

Nov 16 - Nov 17

A white two-story house with a porch, stone steps, and a small garden.

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

Uptown

A two-story house with a front porch, a garage, and a garden with various plants.

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

Downtown Historic District

￥90,105 total

includes taxes & fees

Dec 15 - Dec 16

A single-story house with a white exterior, a front porch with a wooden railing, and a clear sky.

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

Vilano Beach

"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....

B T.

A covered porch with wicker furniture, potted plants, and a white railing.

12. 4bed, 2bath on Iconic Magnolia Ave-walking distance to shops and restaurants!

Uptown

Claudia R.

A covered outdoor seating area with a white brick wall and a sign that reads "Outdoor."

13. Historic Dupont Cottages Retreat

Uptown

￥316,994 total

includes taxes & fees

Dec 15 - Dec 16

View all properties

Learn more about Anastasia Island

Discover the seaside area of Anastasia Island—beaches, natural beauty, and top sights like St. Augustine Beach.

See all hotels in Anastasia Island

A wooden bridge over water with a lighthouse in the background.

Top reviews in Anastasia Island

A covered walkway with a tiled floor, wooden ceiling, and a railing.

Holiday Inn Express St. Augustine - Vilano Beach by IHG

Vilano Beach

10/10 Excellent

Jessica

A small building with a sign reading "Harkey's Court" and a row of wooden chairs outside.

Haleys Court Boutique Motel

Vilano Beach

10/10 Excellent

Shawn

A two-story house with a brick chimney, a green door, and a small patio with a fire pit.

The Collector Inn - Adults Only

St. Augustine Historic District

10/10 Excellent

Absolutely beautiful, with an exceptional staff to match!! The inn is centrally located to everywhere you want to be. Historic St. Augustine is just around the corner, and most attractions or museums are within walking distance. Not too much hustle and bustle, which was a relief.There's maybe three or four large houses, and each house splits into about six suites. The suites are unique and individually decorated. We stayed in the Spears House, in the deluxe king suite w/ sofa bed and balcony....

Ebony

A wooden porch with a railing, a bench, and a view of a historic building with American flags.

St George Inn

St. Augustine Historic District

10/10 Excellent

Stayed at the St George many times over the last 7 years and they never disappoint. The rooms are spacious, clean and tastefully decorated. The St George is perfectly located to all the walking attractions, eating establishment, shops and more. They offer a lovely breakfast every morning with something for everyone both hot and cold varieties plus they have their own wine bar too! . A coffee bar, a cigar shop, and a chocolate shop are located right around the center area as well. Most nights...

DEBRA

A table with a bottle of Meomi wine and two glasses, overlooking a beach with rough waves.

The Saint Augustine Beach House

Vilano Beach

10/10 Excellent

Before booking read some of the reviews and was a bit scared, but the every single employee was very nice, courteous and friendly. The check-in was quick, we received our keys and were escorted to our room. We were told that if we need anything for the kitchen (plates, fork, knife, etc.), or anything else (more towel, pillow, blanket), to let the Front Desk know!!! The room was clean, spacious and charmlng. The view is fantastic (recommend the 2nd or 3rd floor, for better view of the...

Anonymous traveler

A waterfront promenade with a white railing, a bench, and a view of a cityscape across the water.

Edgewater Inn

Davis Shores

10/10 Excellent

Beth

A wooden deck with a table and chairs, overlooking a marina with boats and a building with a red roof.

Inn at Camachee Harbor by Coolvacay

St. Augustine

10/10 Excellent

Susan

A motel with a sign indicating 'No Vacancy' and an American flag.

The Cozy Inn

Nelmar Terrace

10/10 Excellent

Patricia

A hotel with a swimming pool, multiple parking spaces, and a view of the ocean.

La Fiesta Ocean Inn And Suites

St. Augustine

10/10 Excellent

Anthony

A multi-story hotel with a prominent entrance, a sign reading "HYATT PLACE," and a palm tree in front.

Hyatt Place St. Augustine/Vilano Beach

Vilano Beach

10/10 Excellent

Property was in a great location, Publix is located across the street with a few places to eat nearby. There’s also a coffee shop across the street incase you’re looking for coffee and pastries. Parking was convenient(only valet) and they have a courtesy shuttle that will drop you off at the beach/pier. Rooftop bar was nice and their breakfast was delicious. Staff was friendly and super helpful with the exception of check out. She was extremely rude and snapped at me when I asked her a question....

Graciela