A wooden pier extending into calm water at sunset.

Holiday Homes in Anastasia Island

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Check prices for these dates

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

Our top choices for Anastasia Island holiday homes

A backyard with a wooden playhouse, a small pool, and a patio area with chairs.

1. Tropical Bamboo~With large above ground Pool~Outdoor Firepit.

Tropical Bamboo~With large above ground Pool~Outdoor Firepit.
St. Augustine
9.8 out of 10, Exceptional, (6 reviews)
"The place was perfect everything was good. The host was super helpful I would 100% come back ."
United States
Jacob J.
Tropical Bamboo~With large above ground Pool~Outdoor Firepit.
A modern kitchen with a white countertop, two bar stools, and a stainless steel refrigerator.

2. Beautiful home by the Bridge of Lions

Beautiful home by the Bridge of Lions
Davis Shores
9.2 out of 10, Wonderful, (10 reviews)
"We loved our stay at this home in St. Augustine! Absolute perfect location, with an easy and fun walk over the bridge to downtown, plus it's right behind a few great restaurants and bars. "
United States
Dan L.
The price is €228
includes taxes & fees
28 Sept - 29 Sept
Beautiful home by the Bridge of Lions
An aerial view of a large, uniquely shaped building surrounded by dense forest, with a curved pathway leading to it.

3. 617 Sands Dr · 3 Bedroom Brand New House Near Beach | King Bed

617 Sands Dr · 3 Bedroom Brand New House Near Beach | King Bed
St. Augustine
10.0 out of 10, Exceptional, (12 reviews)
"Great stay in a great location for doing activities in St. Augustine! Easy checkin and checkout directions. Would definitely stay here again. "
United States
Pat B.
The price is €285
includes taxes & fees
27 Sept - 28 Sept
617 Sands Dr · 3 Bedroom Brand New House Near Beach | King Bed
A black door with a window, a small shelf with a bowl, and a framed architectural drawing on the wall.

4. Spacious cozy home between downtown & the beach!

Spacious cozy home between downtown & the beach!
Davis Shores
10.0 out of 10, Exceptional, (21 reviews)
"This host was extremely helpful and offered to assist every step of the way. The condo was very nice and clean and in a perfect location to walk downtown or drive to the beac or other restaurants. Perfect stay! "
United States
Keith U.
Spacious cozy home between downtown & the beach!
A modern kitchen with white cabinetry, a wooden ceiling, and a central island.

5. Marshfront 3BR | Walk to Alligator Farm + Lighthouse

Marshfront 3BR | Walk to Alligator Farm + Lighthouse
St. Augustine
9.8 out of 10, Exceptional, (39 reviews)
"Great location - bring or rent bikes and you can get to everything"
United States
Kara L.
The price is €472
includes taxes & fees
27 Sept - 28 Sept
Marshfront 3BR | Walk to Alligator Farm + Lighthouse
A wooden boardwalk leading to a beach at night with a full moon in the sky.

6. Fall & Holiday Deals! NEWLY Remodeled Oceanside Townhouse!!! Pets Pools Bikes!

Fall & Holiday Deals! NEWLY Remodeled Oceanside Townhouse!!! Pets Pools Bikes!
St. Augustine
10.0 out of 10, Exceptional, (9 reviews)
Fall & Holiday Deals! NEWLY Remodeled Oceanside Townhouse!!! Pets Pools Bikes!
A modern kitchen with white cabinetry, a central island with stools, a dining area with a chandelier, and a clock on the wall.

7. Serene 3-bedroom house with AC in charming St. Augustine

Serene 3-bedroom house with AC in charming St. Augustine
St. Augustine
10.0 out of 10, Exceptional, (1 review)
"Very spacious, private, and well equipped. Neighborhood was extremely quiet and safe. It was perfect for solitude, family time, and comfort while simultaneously within close distance to food and activities."
United States
Michael H.
Serene 3-bedroom house with AC in charming St. Augustine
An aerial view of a resort with a distinctive white tent-like structure surrounded by dense forest and a body of water in the background.

8. Madeira Suite: Steps to Music, Markets & Florida Sun

Madeira Suite: Steps to Music, Markets & Florida Sun
St. Augustine
Madeira Suite: Steps to Music, Markets & Florida Sun
An outdoor patio with a fire pit, wooden chairs, string lights, and a wooden wall.

9. Beach house|Hot Tub, DT 7min, Games & Fenced Patio

Beach house|Hot Tub, DT 7min, Games & Fenced Patio
Davis Shores
9.6 out of 10, Exceptional, (28 reviews)
"Everything was very clean and all of the amenities were as listed. We had a great comfortable time even with a large group!"
United States
Jocelyn B.
Beach house|Hot Tub, DT 7min, Games & Fenced Patio
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with stools.

10. Bud's Lighthouse-just steps to St. Augustine Beach

Bud's Lighthouse-just steps to St. Augustine Beach
St. Augustine
10.0 out of 10, Exceptional, (67 reviews)
"Great place everything was as pictured would definitely stay again "
United States
Janice M.
The price is €397
includes taxes & fees
27 Sept - 28 Sept
Bud's Lighthouse-just steps to St. Augustine Beach
A garden pathway leading to a small structure with string lights, surrounded by lush greenery.

11. Madeira Cottage - Amphitheater

Madeira Cottage - Amphitheater
St. Augustine
Madeira Cottage - Amphitheater
An outdoor patio with a pool, wooden pergola, and seating area.

12. Heated Pool Oasis • Walk to Amp • Game Room • Fire Pit

Heated Pool Oasis • Walk to Amp • Game Room • Fire Pit
St. Augustine
10.0 out of 10, Exceptional, (11 reviews)
"What a wonderful place to stay!! We really enjoyed the whole house, especially the pool and fire pit! The host was very helpful and responsive. The beds were very comfortable. Highly recommend and will definitely be back. "
United States
Darby S.
The price is €381
includes taxes & fees
28 Sept - 29 Sept
Heated Pool Oasis • Walk to Amp • Game Room • Fire Pit
A modern living room with a sofa, armchair, coffee table, and a TV mounted on the wall.

13. Walk Downtown • Hot Tub • EV Charger • Fenced Yard

Walk Downtown • Hot Tub • EV Charger • Fenced Yard
Davis Shores
10.0 out of 10, Exceptional, (4 reviews)
"The area was quiet and the house is well furnished with everything you would need to cook. The house very clean and smelled great. "
United States
Beck M.
Walk Downtown • Hot Tub • EV Charger • Fenced Yard
A wooden boardwalk leading to a beach with clear skies.

14. Walk to Beach | 4BR Sleeps 10 + Hot Tub!

Walk to Beach | 4BR Sleeps 10 + Hot Tub!
Butler Beach
9.8 out of 10, Exceptional, (23 reviews)
"Very clean, near the beach, great location."
United States
megan b.
Walk to Beach | 4BR Sleeps 10 + Hot Tub!
A modern house with a white exterior, a small porch, and a view of the ocean and beach.

15. 💲 DIRECT OCEANFRONT COTTAGE 💲 Best Section of Beach - Steps to Beach -Walk to Restaurants

💲 DIRECT OCEANFRONT COTTAGE 💲 Best Section of Beach - Steps to Beach -Walk to Restaurants
St. Augustine
9.8 out of 10, Exceptional, (109 reviews)
"Location is outstanding and the cottage is absolutely adorable! The beds were veey comfortable. "
United States
colleen p.
💲 DIRECT OCEANFRONT COTTAGE 💲 Best Section of Beach - Steps to Beach -Walk to Restaurants
A wooden deck with two green Adirondack chairs, a pineapple, and two cans of beer.

16. Heated Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo, Ping Pong, Pet Friendly

Heated Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo, Ping Pong, Pet Friendly
St. Augustine
10.0 out of 10, Exceptional, (11 reviews)
"Extremely clean and the place had so many fun games. Would recommend to families with kids of all ages"
United States
Joseph S.
Heated Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo, Ping Pong, Pet Friendly
A modern kitchen with white cabinets, stainless steel appliances, and a central island.

17. Walk to Historic District, Fire Pit, Pets OK, Free Parking, Group-Friendly

Walk to Historic District, Fire Pit, Pets OK, Free Parking, Group-Friendly
St. Augustine
9.0 out of 10, Wonderful, (2 reviews)
"Perfect location close enough to walk to everything but not to close so we could sleep great@"
United States
Paul A.
Walk to Historic District, Fire Pit, Pets OK, Free Parking, Group-Friendly
A living room with a sectional sofa, a fireplace, a television, and a large window.

18. The Southwind|Pool|3-Min Drive to Beach|Sleeps 10

The Southwind|Pool|3-Min Drive to Beach|Sleeps 10
St. Augustine
10.0 out of 10, Exceptional, (1 review)
"Perfect location! Property was clean and perfect for our getaway trip!"
United States
Rhonda K.
The price is €450
includes taxes & fees
14 Oct - 15 Oct
The Southwind|Pool|3-Min Drive to Beach|Sleeps 10
A covered patio area with wicker furniture, including a sofa and chairs, and a wooden table.

19. Pool, Hot Tub, Enclosed Patio, Close to Everything-A Million Memories

Pool, Hot Tub, Enclosed Patio, Close to Everything-A Million Memories
Davis Shores
10.0 out of 10, Exceptional, (12 reviews)
"Loved the calm vibe especially on the back porch! Everything was clean and inviting and the host was very responsive. "
United States
Kandice A.
Pool, Hot Tub, Enclosed Patio, Close to Everything-A Million Memories
A staircase with wooden steps leading to a white door.

20. Crescent Beach 4BR | Walk to Beach | Sleeps 12

Crescent Beach 4BR | Walk to Beach | Sleeps 12
Butler Beach
10.0 out of 10, Exceptional, (18 reviews)
"We are very nice and we enjoy the place "
United States
Maria J M.
Crescent Beach 4BR | Walk to Beach | Sleeps 12
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

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

8/10 Good
"The room we had was really nice. It was a king bed/studio. Pretty big with a huge deck overlooking the ocean. Nice pool, nice chairs, pool bar."
Leslie 2-night trip
Posted 2 hours ago
Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

Find out more about Anastasia Island

Anastasia Island Holiday Homes information

Number of reviews
345
Accommodation
688 Holiday Homes
Lowest Price
€228
Highest Price
€472

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