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. The Beach Club by Coolvacay

The Beach Club by Coolvacay
3.5 star property
St. Augustine
9.6 out of 10, Exceptional, (22 reviews)
"Everything was awesome. Will stay there again!!"
United States
Rich
The price is NZ$419
includes taxes & fees
22 Aug - 23 Aug
The Beach Club by Coolvacay

2. Oceans 13 Unit A

Oceans 13 Unit A
3.0 star property
St. Augustine
10.0 out of 10, Exceptional, (5 reviews)
"Love that you are walking distance to restaurants and beach will be back soon"
United States
Belinda
The price is NZ$727
includes taxes & fees
19 Aug - 20 Aug
Oceans 13 Unit A

3. Walk to St Aug Beach or Explore the Oldest City- 2 Bedroom villa with hot tub

Walk to St Aug Beach or Explore the Oldest City- 2 Bedroom villa with hot tub
Butler Beach
9.6 out of 10, Exceptional, (85 reviews)
"We loved our stay at the Sunny Dayz! The house was clean & had everything we needed to cook. We enjoyed the board games and puzzles. We loved the hot tub, super clean and relaxing. Would recommend to anyone staying in St. Augustine!"
United States
Savannah
The price is NZ$439
includes taxes & fees
19 Aug - 20 Aug
Walk to St Aug Beach or Explore the Oldest City- 2 Bedroom villa with hot tub

4. 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, (90 reviews)
"We had such a great time. Perfect location and beautiful property!"
United States
Leian E.
The price is NZ$542
includes taxes & fees
21 Aug - 22 Aug
Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants

5. 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, (111 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.
The price is NZ$747
includes taxes & fees
19 Aug - 20 Aug
Amazing Ocean Views, Steps to Beach, Walk to Restaurants, Shops, and Pier! $300 in Free Tickets!

6. St. Augustine Beach Community

St. Augustine Beach Community
Butler Beach
9.6 out of 10, Exceptional, (99 reviews)
"Very nice place to stay in a dog friendly property. Unit was as advertised and the king bed was very comfortable. Great location!"
United States
Charles A.
The price is NZ$325
includes taxes & fees
19 Aug - 20 Aug
St. Augustine Beach Community

7. Steps to Beach! Suite Bedrooms, Walk to Shops and Pier, Minutes to Downtown, $300 in Free Tickets!

Steps to Beach! Suite Bedrooms, Walk to Shops and Pier, Minutes to Downtown, $300 in Free Tickets!
Saint Augustine
9.8 out of 10, Exceptional, (139 reviews)
"Great location! "
United States
Chris H.
The price is NZ$749
includes taxes & fees
19 Aug - 20 Aug
Steps to Beach! Suite Bedrooms, Walk to Shops and Pier, Minutes to Downtown, $300 in Free Tickets!

8. 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$646
includes taxes & fees
19 Aug - 20 Aug
Island Suite l Walk to Downtown!

9. Walk to town, short drive to the beach.

Walk to town, short drive to the beach.
Davis Shores
9.8 out of 10, Exceptional, (105 reviews)
"Such a great location. Nice walk to downtown and a short drive to the beach. Had the best time. Beds are also super comfy."
United States
Kayla K.
The price is NZ$389
includes taxes & fees
19 Aug - 20 Aug
Walk to town, short drive to the beach.

10. Beautiful home by the Bridge of Lions

Beautiful home by the Bridge of Lions
Davis Shores
9.8 out of 10, Exceptional, (8 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$426
includes taxes & fees
31 Aug - 1 Sept
Beautiful home by the Bridge of Lions

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

Waterfront suite, Dogs are cool! no pet fee!
Butler Beach
10.0 out of 10, Exceptional, (30 reviews)
"Cordial hosts, quiet area. "
United States
Amy I.
The price is NZ$230
includes taxes & fees
19 Aug - 20 Aug
Waterfront suite, Dogs are cool! no pet fee!

12. Duneside Bliss l Hot Tub l Firepit l Dogs OK

Duneside Bliss l Hot Tub l Firepit l Dogs OK
St. Augustine
10.0 out of 10, Exceptional, (43 reviews)
"Yes. We loved our stay!"
United States
Elena W.
The price is NZ$955
includes taxes & fees
15 Sept - 16 Sept
Duneside Bliss l Hot Tub l Firepit l Dogs OK

13. 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$481
includes taxes & fees
23 Aug - 24 Aug
Ocean Village Club-Sleeps 4 with First Floor Access and Screen Porch

14. 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, (25 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 NZ$690
includes taxes & fees
24 Aug - 25 Aug
St. Augustine Beach, Florida: 2 bed/2 bath (Beachfront PetFriendly Free Parking)

15. Ocean Front 1 Bed room Condo With Heated Pool just outside the balcony Unit 101

Ocean Front 1 Bed room Condo With Heated Pool just outside the balcony Unit 101
Crescent Beach
9.4 out of 10, Exceptional, (139 reviews)
"Loved the pool access!"
United States
Kady
The price is NZ$358
includes taxes & fees
23 Aug - 24 Aug
Ocean Front 1 Bed room Condo With Heated Pool just outside the balcony Unit 101

16. Spacious cozy home between downtown & the beach!

Spacious cozy home between downtown & the beach!
Davis Shores
9.8 out of 10, Exceptional, (19 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 NZ$378
includes taxes & fees
7 Sept - 8 Sept
Spacious cozy home between downtown & the beach!

17. 3BR/2BA Scenic Marsh & Birding Coastal Retreat

3BR/2BA Scenic Marsh & Birding Coastal Retreat
St. Augustine
9.8 out of 10, Exceptional, (37 reviews)
"Great location - bring or rent bikes and you can get to everything"
United States
Kara L.
The price is NZ$925
includes taxes & fees
20 Aug - 21 Aug
3BR/2BA Scenic Marsh & Birding Coastal Retreat

18. 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, (35 reviews)
"Very cute and clean house in a very convenient area. Would stay there again"
United States
Chrissy H.
The price is NZ$723
includes taxes & fees
19 Aug - 20 Aug
Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable

19. 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)
"Wonderful stay!"
United States
Kelly L.
Ocean Front Condo With Heated Pool outdoor patio overlooking the Ocean

20. 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$745
includes taxes & fees
24 Aug - 25 Aug
Bud's Lighthouse-just steps to St. Augustine Beach
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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