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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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.
The price is NZ$550
includes taxes & fees
6 Oct - 7 Oct
Tropical Bamboo~With large above ground Pool~Outdoor Firepit.
A wooden boardwalk leading to a beach at night with a full moon in the sky.

2. 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)
"Portside is the perfect location. Just steps from the pool and the beach! The host is incredibly responsive and provided us with all the info we needed for a wonderful week. The home is great, comfortable, and we had an amazing time. We definitely want to go back!"
United States
Anonymous traveller
The price is NZ$713
includes taxes & fees
1 Oct - 2 Oct
Fall & Holiday Deals! NEWLY Remodeled Oceanside Townhouse!!! Pets Pools Bikes!
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 NZ$568
includes taxes & fees
6 Oct - 7 Oct
617 Sands Dr · 3 Bedroom Brand New House Near Beach | King Bed
A modern kitchen with white cabinetry, a wooden ceiling, and a central island.

4. 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 NZ$947
includes taxes & fees
1 Oct - 2 Oct
Marshfront 3BR | Walk to Alligator Farm + Lighthouse
A modern kitchen with a white countertop, two bar stools, and a stainless steel refrigerator.

5. 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 NZ$477
includes taxes & fees
14 Oct - 15 Oct
Beautiful home by the Bridge of Lions
A modern kitchen with white cabinetry, a central island with stools, a dining area with a chandelier, and a clock on the wall.

6. 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.
The price is NZ$666
includes taxes & fees
1 Oct - 2 Oct
Serene 3-bedroom house with AC in charming St. Augustine
A garden pathway leading to a small structure with string lights, surrounded by lush greenery.

7. Madeira Cottage - Amphitheater

Madeira Cottage - Amphitheater
St. Augustine
The price is NZ$618
includes taxes & fees
6 Oct - 7 Oct
Madeira Cottage - Amphitheater
A modern house with a white exterior, a small porch, and a view of the ocean and beach.

8. 💲 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.
The price is NZ$897
includes taxes & fees
6 Oct - 7 Oct
💲 DIRECT OCEANFRONT COTTAGE 💲 Best Section of Beach - Steps to Beach -Walk to Restaurants
A modern living room with a sofa, armchair, coffee table, and a TV mounted on the wall.

9. 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.
The price is NZ$782
includes taxes & fees
13 Oct - 14 Oct
Walk Downtown • Hot Tub • EV Charger • Fenced Yard
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 NZ$775
includes taxes & fees
1 Oct - 2 Oct
Bud's Lighthouse-just steps to St. Augustine Beach
An outdoor patio with a fire pit, wooden chairs, string lights, and a wooden wall.

11. 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.
The price is NZ$728
includes taxes & fees
1 Oct - 2 Oct
Beach house|Hot Tub, DT 7min, Games & Fenced Patio
A modern two-story house with a garage, surrounded by lush greenery and a paved driveway.

12. Anastasia Island Villa Duplex Single Level EV

Anastasia Island Villa Duplex Single Level EV
Davis Shores
10.0 out of 10, Exceptional, (2 reviews)
"This house is amazing. Close to beaches and restaurants. Very nice quiet neighborhood."
United States
louise c.
The price is NZ$676
includes taxes & fees
26 Oct - 27 Oct
Anastasia Island Villa Duplex Single Level EV
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.

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

Madeira Suite: Steps to Music, Markets & Florida Sun
St. Augustine
The price is NZ$602
includes taxes & fees
6 Oct - 7 Oct
Madeira Suite: Steps to Music, Markets & Florida Sun
A modern kitchen with stainless steel appliances, a central island with bar stools, and a view to the outside.

14. Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable

Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable
Davis Shores
10.0 out of 10, Exceptional, (43 reviews)
"Very cute and clean house in a very convenient area. Would stay there again"
United States
Chrissy H.
The price is NZ$912
includes taxes & fees
1 Oct - 2 Oct
Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable
A covered patio area with wicker furniture, including a sofa and chairs, and a wooden table.

15. 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 property and the location. Was exactly what we were looking for!"
United States
Nathan W.
The price is NZ$770
includes taxes & fees
6 Oct - 7 Oct
Pool, Hot Tub, Enclosed Patio, Close to Everything-A Million Memories
A modern kitchen with white cabinets, stainless steel appliances, and a central island.

16. 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.
The price is NZ$1,319
includes taxes & fees
5 Oct - 6 Oct
Walk to Historic District, Fire Pit, Pets OK, Free Parking, Group-Friendly
A kitchen with a large island, white cabinetry, and pendant lighting.

17. Sunshine Dip - Sleeps 8, Relaxing, Pool, WIFI

Sunshine Dip - Sleeps 8, Relaxing, Pool, WIFI
Davis Shores
9.6 out of 10, Exceptional, (5 reviews)
"My daughter and I had a fun couple days in this beautifully decorated house. Loved the neighborhood and had a great time "
United States
Kelly W.
The price is NZ$848
includes taxes & fees
19 Oct - 20 Oct
Sunshine Dip - Sleeps 8, Relaxing, Pool, WIFI
A wooden boardwalk leading to a beach with clear skies.

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

Walk to Beach | 4BR Sleeps 10 + Hot Tub!
Butler Beach
9.8 out of 10, Exceptional, (24 reviews)
"Very clean, near the beach, great location."
United States
megan b.
The price is NZ$1,169
includes taxes & fees
1 Oct - 2 Oct
Walk to Beach | 4BR Sleeps 10 + Hot Tub!
A wooden deck with two green Adirondack chairs, a pineapple, and two cans of beer.

19. 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.
The price is NZ$862
includes taxes & fees
6 Oct - 7 Oct
Heated Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo, Ping Pong, Pet Friendly
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a table and chairs.

20. 3 minute walk to the beach, outdoor shower, pet friendly, close to downtown

3 minute walk to the beach, outdoor shower, pet friendly, close to downtown
Butler Beach
10.0 out of 10, Exceptional, (33 reviews)
"Everything was great! Perfect little house for a beach getaway!"
United States
Rey P.
The price is NZ$713
includes taxes & fees
6 Oct - 7 Oct
3 minute walk to the beach, outdoor shower, pet friendly, close to downtown
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

Regency Inn & Suites

Regency Inn & Suites

8/10 Good
"Buen lugar, limpio y Buen precio"
Ramon 1-night trip
Posted 5 hours ago
Regency Inn & Suites

Find out more about Anastasia Island

Anastasia Island Holiday Homes information

Number of reviews
376
Accommodation
689 Holiday Homes
Lowest Price
NZ$477
Highest Price
NZ$1,319

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