A wooden pier extending into calm water at sunset.

Anastasia Island Holiday Rentals

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Our top choices for Anastasia Island holiday 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, (212 reviews)
"The location and Condo were amazing"
United States
Eugenio M.
The price is NZ$389
includes taxes & fees
25 Oct - 26 Oct
1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24

2. Stunning 1 Bed 1 Bath Condo with Heated Pool B-15

Stunning 1 Bed 1 Bath Condo with Heated Pool B-15
Butler Beach
9.8 out of 10, Exceptional, (61 reviews)
"Great location and very responsive host."
United States
Louis D.
The price is NZ$395
includes taxes & fees
29 Oct - 30 Oct
Stunning 1 Bed 1 Bath Condo with Heated Pool B-15

3. Beach Side complex B35 1 Bedroom 1 Bath with Heated Pool

Beach Side complex B35 1 Bedroom 1 Bath with Heated Pool
Butler Beach
9.8 out of 10, Exceptional, (81 reviews)
"We were very impressed with the property! Super clean, comfortable and quiet. Would stay here again!"
United States
Bette D.
The price is NZ$441
includes taxes & fees
24 Oct - 25 Oct
Beach Side complex B35 1 Bedroom 1 Bath with Heated Pool

4. 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 NZ$396
includes taxes & fees
12 Oct - 13 Oct
Oceanside complex B-17 1 bedroom with Heated Pool

5. St. Augustine's Oceanfront Oasis: Hibiscus F102

St. Augustine's Oceanfront Oasis: Hibiscus F102
3.0 star property
Butler Beach
The price is NZ$908
includes taxes & fees
24 Oct - 25 Oct
St. Augustine's Oceanfront Oasis: Hibiscus F102

6. 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 NZ$576
includes taxes & fees
22 Oct - 23 Oct
Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants

7. 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$482
includes taxes & fees
14 Oct - 15 Oct
Beautiful home by the Bridge of Lions

8. 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.
Steps to Sand! New Updates! Sunroom, Suites, Walk to Restaurants, Shops, Pier! $300 in Free Tickets!

9. Ocean View Villa ~ Fenced Yard ~ Pet Friendly ~ Steps to the Beach!!!

Ocean View Villa ~ Fenced Yard ~ Pet Friendly ~ Steps to the Beach!!!
Saint Augustine
9.6 out of 10, Exceptional, (72 reviews)
"We enjoyed our stay. The beach was only steps away. The house was clean and pet friendly. We would recommend it to others and would stay again."
United States
Nicole P.
Ocean View Villa ~ Fenced Yard ~ Pet Friendly ~ Steps to the Beach!!!

10. 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)
"Our first time visiting and will definitely be bringing our family back next yr !!"
United States
GREG G.
The price is NZ$618
includes taxes & fees
5 Oct - 6 Oct
St. Augustine Beach, Florida: 2 bed/2 bath (Beachfront PetFriendly Free Parking)

11. 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 NZ$411
includes taxes & fees
13 Oct - 14 Oct
Island Suite l Walk to Downtown!

12. 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 NZ$506
includes taxes & fees
4 Oct - 5 Oct
Ocean Village Club-Sleeps 4 with First Floor Access and Screen Porch

13. 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$952
includes taxes & fees
4 Oct - 5 Oct
Marshfront 3BR | Walk to Alligator Farm + Lighthouse

14. Ocean Front Condo With Heated Pool outdoor patio overlooking the Ocean

Ocean Front Condo With Heated Pool outdoor patio overlooking the Ocean
Crescent Beach
9.0 out of 10, Wonderful, (128 reviews)
"Right on the beach with all accommodations needed. Clean and affordable. Host even provides a long blow up mattress and a play pen if needed. We LOVED our stay and will definitely be back!"
United States
Anonymous traveller
Ocean Front Condo With Heated Pool outdoor patio overlooking the Ocean

15. 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 NZ$904
includes taxes & fees
12 Oct - 13 Oct
Seaside Sanctuary: Relax in St. Augustine's Gem

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

Waterfront suite, Dogs are cool! no pet fee!
Butler Beach
10.0 out of 10, Exceptional, (35 reviews)
"Cordial hosts, quiet area. "
United States
Amy I.
The price is NZ$258
includes taxes & fees
15 Oct - 16 Oct
Waterfront suite, Dogs are cool! no pet fee!

17. 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 NZ$406
includes taxes & fees
5 Oct - 6 Oct
215 Beachers Lodge Direct Ocean Front Crescent Beach One Bedroom Condo

18. 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$776
includes taxes & fees
7 Oct - 8 Oct
Beach house|Hot Tub, DT 7min, Games & Fenced Patio

19. 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 NZ$779
includes taxes & fees
8 Oct - 9 Oct
Spectacular Oceanfront Views ~ Olympic Sized Heated Oceanfront Pool

20. 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$873
includes taxes & fees
4 Oct - 5 Oct
Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable
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

Find out more about Anastasia Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Anastasia Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Anastasia Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Anastasia Island. Seeing all the best attractions is bound to make you fall in love with Anastasia Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Anastasia Island short-term rentals, that won’t be hard to do.

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