A wooden pier extending into calm water at sunset.

Anastasia Island Vacation Rentals

  • 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 vacation rentals

1. 1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24

1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24
St. Augustine
9.6 out of 10, Exceptional, (211 reviews)
"The location and Condo were amazing"
United States
Eugenio M.
The price is ¥12,442
¥34,799 total
includes taxes & fees
Oct 11 - Oct 12
1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24

2. The Beach Club by Coolvacay

The Beach Club by Coolvacay
3.5 star property
St. Augustine
9.4 out of 10, Exceptional, (36 reviews)
"Great place"
United States
Irving
The Beach Club by Coolvacay

3. Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants

Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants
St. Augustine
9.8 out of 10, Exceptional, (95 reviews)
"We had such a great time. Perfect location and beautiful property!"
United States
Leian E.
The price is ¥20,845
¥50,983 total
includes taxes & fees
Sep 27 - Sep 28
Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants

4. Island Suite l Walk to Downtown!

Island Suite l Walk to Downtown!
Davis Shores
10.0 out of 10, Exceptional, (38 reviews)
"Great place, close to attractions and owners are very nice! Definitely would stay again! "
United States
Regina S.
The price is ¥11,068
¥59,695 total
includes taxes & fees
Oct 1 - Oct 2
Island Suite l Walk to Downtown!

5. Oceanside complex B-17 1 bedroom with Heated Pool

Oceanside complex B-17 1 bedroom with Heated Pool
Butler Beach
9.6 out of 10, Exceptional, (35 reviews)
"The condo had everything we needed for a nice getaway including beach access"
United States
Rhonda L.
The price is ¥12,765
¥35,491 total
includes taxes & fees
Sep 27 - Sep 28
Oceanside complex B-17 1 bedroom with Heated Pool

6. 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.
The price is ¥12,550
¥35,298 total
includes taxes & fees
Sep 29 - Sep 30
Spacious cozy home between downtown & the beach!

7. Waterfront suite, Dogs are cool! no pet fee!

Waterfront suite, Dogs are cool! no pet fee!
Butler Beach
10.0 out of 10, Exceptional, (32 reviews)
"Cordial hosts, quiet area. "
United States
Amy I.
The price is ¥13,978
¥18,725 total
includes taxes & fees
Sep 23 - Sep 24
Waterfront suite, Dogs are cool! no pet fee!

8. 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 ¥12,550
¥39,690 total
includes taxes & fees
Sep 29 - Sep 30
Beautiful home by the Bridge of Lions

9. Seaside Sanctuary: Relax in St. Augustine's Gem

Seaside Sanctuary: Relax in St. Augustine's Gem
2.5 star property
Butler Beach
The price is ¥13,354
¥79,852 total
includes taxes & fees
Sep 26 - Sep 27
Seaside Sanctuary: Relax in St. Augustine's Gem

10. Ocean Village Club-Sleeps 4 with First Floor Access and Screen Porch

Ocean Village Club-Sleeps 4 with First Floor Access and Screen Porch
Butler Beach
9.4 out of 10, Exceptional, (32 reviews)
"Perfect for a weekend getaway!"
United States
Roman M.
The price is ¥17,649
¥44,345 total
includes taxes & fees
Sep 27 - Sep 28
Ocean Village Club-Sleeps 4 with First Floor Access and Screen Porch

11. Amazing Ocean Views, Steps to Beach, Walk to Restaurants, Shops, and Pier! $300 in Free Tickets!

Amazing Ocean Views, Steps to Beach, Walk to Restaurants, Shops, and Pier! $300 in Free Tickets!
St. Augustine Beach
10.0 out of 10, Exceptional, (113 reviews)
"My husband and I enjoyed our stay. The location was perfect. The beach access was close that we walked the beach every morning and evening. Will definitely stay here again."
United States
Heather S.
Amazing Ocean Views, Steps to Beach, Walk to Restaurants, Shops, and Pier! $300 in Free Tickets!

12. St. Augustine Beach, Florida: 2 bed/2 bath (Beachfront PetFriendly Free Parking)

St. Augustine Beach, Florida: 2 bed/2 bath (Beachfront PetFriendly Free Parking)
Butler Beach
10.0 out of 10, Exceptional, (26 reviews)
"This location was awesome! It was a very short walk to the private access beach which was great! We definitely enjoyed our stay."
United States
Juli M.
The price is ¥19,061
¥63,141 total
includes taxes & fees
Oct 5 - Oct 6
St. Augustine Beach, Florida: 2 bed/2 bath (Beachfront PetFriendly Free Parking)

13. 💲DIRECT OCEANFRONT Romantic Cottage💲 Best Beach - Walk to Restaurants - Downtown only 5 Miles

💲DIRECT OCEANFRONT Romantic Cottage💲 Best Beach - Walk to Restaurants - Downtown only 5 Miles
St. Augustine
9.8 out of 10, Exceptional, (144 reviews)
"Fantastic place, easy access to beach and nearby restaurants. Super close to St. Augustine. Will definitely check out in the future if we return!"
United States
Steven G.
💲DIRECT OCEANFRONT Romantic Cottage💲 Best Beach - Walk to Restaurants - Downtown only 5 Miles

14. Beautifully updated 2 bedroom ocean-view townhouse in the heart of St. Augustine

Beautifully updated 2 bedroom ocean-view townhouse in the heart of St. Augustine
St. Augustine Beach
9.8 out of 10, Exceptional, (40 reviews)
"We loved our stay here! The property was exactly as pictured and very clean. It was also much closer to the beach than expected."
United States
Ansley H.
The price is ¥30,948
¥80,566 total
includes taxes & fees
Sep 23 - Sep 24
Beautifully updated 2 bedroom ocean-view townhouse in the heart of St. Augustine

15. Spectacular Oceanfront Views ~ Olympic Sized Heated Oceanfront Pool

Spectacular Oceanfront Views ~ Olympic Sized Heated Oceanfront Pool
Crescent Beach
9.6 out of 10, Exceptional, (214 reviews)
"Perfect place to relax for a few days. The bed was very comfortable and the view from the balcony was beautiful!"
United States
Mary Q.
The price is ¥17,429
¥65,938 total
includes taxes & fees
Sep 23 - Sep 24
Spectacular Oceanfront Views ~ Olympic Sized Heated Oceanfront Pool

16. Steps to Sand! New Updates! Sunroom, Suites, Walk to Restaurants, Shops, Pier! $300 in Free Tickets!

Steps to Sand! New Updates! Sunroom, Suites, Walk to Restaurants, Shops, Pier! $300 in Free Tickets!
St. Augustine
9.6 out of 10, Exceptional, (114 reviews)
"Can not beat the location and well maintained!!! Would stay again!!"
United States
Jim F.
The price is ¥30,096
¥79,750 total
includes taxes & fees
Oct 17 - Oct 18
Steps to Sand! New Updates! Sunroom, Suites, Walk to Restaurants, Shops, Pier! $300 in Free Tickets!

17. 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, (40 reviews)
"Very cute and clean house in a very convenient area. Would stay there again"
United States
Chrissy H.
The price is ¥31,376
¥73,597 total
includes taxes & fees
Sep 27 - Sep 28
Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable

18. 215 Beachers Lodge Direct Ocean Front Crescent Beach One Bedroom Condo

215 Beachers Lodge Direct Ocean Front Crescent Beach One Bedroom Condo
Crescent Beach
9.0 out of 10, Wonderful, (69 reviews)
"Beach view was amazing, the boardwalk takes you right to what feels like a secluded beach. The heated pool was also perfectly warm!"
United States
Nancy J.
The price is ¥15,418
¥37,764 total
includes taxes & fees
Oct 5 - Oct 6
215 Beachers Lodge Direct Ocean Front Crescent Beach One Bedroom Condo

19. View Ocean & Racquet 8315

View Ocean & Racquet 8315
2.0 star property
Butler Beach
The price is ¥13,354
¥79,852 total
includes taxes & fees
Oct 17 - Oct 18
View Ocean & Racquet 8315

20. 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 ¥24,379
¥62,658 total
includes taxes & fees
Sep 23 - Sep 24
Beach house|Hot Tub, DT 7min, Games & Fenced Patio
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

Search for holiday rentals in Anastasia Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Anastasia Island using one of the methods below:

  • View our selection of featured holiday rentals in Anastasia Island
  • Use the map to find apartments and other holiday homes in the Anastasia Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Anastasia Island while they last

Look no further and take a look at our great range of rental properties in Anastasia Island!

Explore a world of travel with Expedia