A wooden pier extending into calm water at sunset.

Anastasia Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Anastasia Island vacation rentals

A swimming pool with lounge chairs and palm trees.

1. 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, (62 reviews)
"Our stay was amazing ! Todd was an outstanding host & his communication was wonderful. We will truely be staying again!"
United States
Heather W.
$195 nightly
The price is $216
Nov 20 - Nov 21
Total with taxes and fees
Stunning 1 Bed 1 Bath Condo with Heated Pool B-15
A beach with sand dunes and sparse vegetation.

2. The Beach Club by Coolvacay

The Beach Club by Coolvacay
3.5 star property
St. Augustine
9.2 out of 10, Wonderful, (45 reviews)
"We really loved it and will definitely be going back"
United States
PAUL J
The Beach Club by Coolvacay
A wooden boardwalk leading to a sandy beach with ocean waves in the background.

3. 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, (216 reviews)
"Nice property,close to pools and beach."
United States
Julie B.
$204 nightly
The price is $225
Nov 23 - Nov 24
Total with taxes and fees
1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24
Pool

4. Chic Resort-style Condo, Beachfront & Pool View

Chic Resort-style Condo, Beachfront & Pool View
3.5 star property
Butler Beach
$468 nightly
The price is $522
Nov 16 - Nov 17
Total with taxes and fees
Chic Resort-style Condo, Beachfront & Pool View
A residential area with a swimming pool, lounge chairs, and a fenced patio area.

5. Anastasia Hideaway 6 Min Walk to Beach Community Pool Near Dining & Amphitheatre

Anastasia Hideaway 6 Min Walk to Beach Community Pool Near Dining & Amphitheatre
St. Augustine
10.0 out of 10, Exceptional, (10 reviews)
"Perfect week stay, the pool was close by and the beach was a short walk. We enjoyed the quietness, truly made for a relaxing vacation."
United States
Sarah L.
$260 nightly
The price is $288
Nov 15 - Nov 16
Total with taxes and fees
Anastasia Hideaway 6 Min Walk to Beach Community Pool Near Dining & Amphitheatre
A wooden boardwalk leading to a sandy beach with ocean waves in the background.

6. 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, (82 reviews)
"Our stay was wonderful, the property is in great location, room was clean and the host was super helpful and super quick to reply! Will be looking forward to booking again in the future!"
United States
Erick G.
$207 nightly
The price is $228
Nov 24 - Nov 25
Total with taxes and fees
Beach Side complex B35 1 Bedroom 1 Bath with Heated Pool
A modern kitchen with white cabinets, stainless steel appliances, and a white dining table with bar stools.

7. Deja Blue l Fire pit l Steps to Beach l Dogs OK

Deja Blue l Fire pit l Steps to Beach l Dogs OK
St. Augustine
9.8 out of 10, Exceptional, (49 reviews)
"Great location to explore the area. Will definitely stay again."
United States
derek p.
$224 nightly
The price is $248
Nov 15 - Nov 16
Total with taxes and fees
Deja Blue l Fire pit l Steps to Beach l Dogs OK
A clear swimming pool with a metal frame and tiled edges, surrounded by a wooden fence and potted plants.

8. Starfish - Screened Heated Pool, 6 Bedrooms, Near Downtown & Amphitheatre

Starfish - Screened Heated Pool, 6 Bedrooms, Near Downtown & Amphitheatre
St. Augustine
9.6 out of 10, Exceptional, (163 reviews)
"We really enjoyed our stay!! Nice open floor plan, plenty of space for our group, nice pool, quiet neighborhood, convenient to beach and downtown. Host prompt and very accommodating."
United States
Heather B.
$459 nightly
The price is $505
Nov 15 - Nov 16
Total with taxes and fees
Starfish - Screened Heated Pool, 6 Bedrooms, Near Downtown & Amphitheatre
Pool

9. 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.
$196 nightly
The price is $217
Nov 20 - Nov 21
Total with taxes and fees
Oceanside complex B-17 1 bedroom with Heated Pool
A pool area with a small building, surrounded by greenery and palm trees.

10. Home away from home! Short walk to the beach and more! Prime Location!

Home away from home! Short walk to the beach and more! Prime Location!
St. Augustine
10.0 out of 10, Exceptional, (52 reviews)
"What a Great place! Close to the beach, clean and very comfortable, highly Recommend! Will definitely book this place again!!"
United States
Bill M.
$288 nightly
The price is $319
Nov 15 - Nov 16
Total with taxes and fees
Home away from home! Short walk to the beach and more! Prime Location!
A spacious living room with a large window offering a view of the beach and ocean.

11. 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, (100 reviews)
"This was our second year in a row to stay here and we would return again! The condo is immaculate, contains everything you might need for a great beach experience, and is located in a great spot. With an oceanfront view, on-site pool, and yummy restaurants on either side and across the street you could spend the entire week here without the need to get in your car. Highly recommend!"
United States
Steven D.
$296 nightly
The price is $326
Nov 15 - Nov 16
Total with taxes and fees
Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants
An aerial view of a swimming pool with multiple lounge chairs and a clear blue water surface.

12. Paradise Palms - Nautilus Suite - Heated Pool!

Paradise Palms - Nautilus Suite - Heated Pool!
Coquina Gables
9.6 out of 10, Exceptional, (17 reviews)
"Great location & amenities "
United States
lee g.
$260 nightly
The price is $289
Nov 16 - Nov 17
Total with taxes and fees
Paradise Palms - Nautilus Suite - Heated Pool!
A dining area with a pool view, a kitchen with modern appliances, and a chandelier.

13. Southwind - Screened Heated Pool, Near Beach, Downtown & Amphitheatre

Southwind - Screened Heated Pool, Near Beach, Downtown & Amphitheatre
St. Augustine
9.6 out of 10, Exceptional, (151 reviews)
"The home was beautiful. We enjoyed the pool and the proximity to everything."
United States
Kathy S.
$459 nightly
The price is $505
Nov 15 - Nov 16
Total with taxes and fees
Southwind - Screened Heated Pool, Near Beach, Downtown & Amphitheatre
A sandy pathway flanked by dense green vegetation, leading to a beach.

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

St. Augustine's Oceanfront Oasis: Hibiscus F102
3.0 star property
Butler Beach
4.0 out of 10, (1 review)
"We had a few issues with our stay. Upon arrival the condo assigned to us had not been cleaned at all and looked to be in a relatively tired condition compared to the photos we saw online. We were helped to quickly find an alternative condo and the team were very responsive however, there were a few general cleanliness issues once we finally got settled like dirt / hair on floor near and under the bed and a cockroach in one of our towels! Location was OK but nothing special. I"
United Kingdom
Alexander
$464 nightly
The price is $518
Nov 21 - Nov 22
Total with taxes and fees
St. Augustine's Oceanfront Oasis: Hibiscus F102
A living room with a brown sofa, a coffee table, a TV, and a cabinet with decorative items.

15. 2-bed 2 bath condo in St. Augustine Beach with pool, resturants,shops and more!

2-bed 2 bath condo in St. Augustine Beach with pool, resturants,shops and more!
St. Augustine
8.6 out of 10, Excellent, (8 reviews)
"Close to everything!! Great place for beach and if visiting for concerts at the amphitheater. "
United States
Kandie S.
$266 nightly
The price is $296
Nov 16 - Nov 17
Total with taxes and fees
2-bed 2 bath condo in St. Augustine Beach with pool, resturants,shops and more!
An aerial view of a large, uniquely shaped building surrounded by dense forest, with a curved pathway leading to it.

16. 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.
$281 nightly
The price is $311
Nov 15 - Nov 16
Total with taxes and fees
617 Sands Dr · 3 Bedroom Brand New House Near Beach | King Bed
A sunset over the ocean with clouds reflecting on the water.

17. Lighthouse & Beach Retreat - Heated Pool, Near Beach, Downtown & Amphitheatre

Lighthouse & Beach Retreat - Heated Pool, Near Beach, Downtown & Amphitheatre
St Augustine
9.4 out of 10, Exceptional, (174 reviews)
"Great place ."
United States
Cathy
$425 nightly
The price is $468
Nov 15 - Nov 16
Total with taxes and fees
Lighthouse & Beach Retreat - Heated Pool, Near Beach, Downtown & Amphitheatre
A sunset over the ocean with clouds reflecting on the water.

18. Sail Away - Heated Pool, Walk to Amphitheatre, Pet Friendly, Near Beach

Sail Away - Heated Pool, Walk to Amphitheatre, Pet Friendly, Near Beach
St. Augustine
10.0 out of 10, Exceptional, (82 reviews)
"Perfect place for a girlfriend weekend! Host was accommodating, plenty of room for 8 women. Loved the pool and proximity to the beach and The Amp."
United States
Julie
$448 nightly
The price is $493
Nov 15 - Nov 16
Total with taxes and fees
Sail Away - Heated Pool, Walk to Amphitheatre, Pet Friendly, Near Beach
A beach scene with a sunset, sandy shore, and a tree in the foreground.

19. Beautiful home by the Bridge of Lions

Beautiful home by the Bridge of Lions
Davis Shores
9.4 out of 10, Exceptional, (12 reviews)
"Very clean, nice area, convenient to tourist locations"
United States
Lori
$248 nightly
The price is $248
Nov 29 - Nov 30
Total with taxes and fees
Beautiful home by the Bridge of Lions
An aerial view of a swimming pool with multiple lounge chairs and a clear blue water surface.

20. Sand Dollar Suite l Heated Pool l Steps to Beach

Sand Dollar Suite l Heated Pool l Steps to Beach
Coquina Gables
9.6 out of 10, Exceptional, (24 reviews)
"I’m coming back"
United States
Anastasia
$281 nightly
The price is $313
Nov 16 - Nov 17
Total with taxes and fees
Sand Dollar Suite l Heated Pool l Steps to 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

Holiday Inn Express St. Augustine near Dtwn - Historic by IHG

Holiday Inn Express St. Augustine near Dtwn - Historic by IHG

10/10 Excellent
"It was clean, food was delicious, the staff was knowledgeable about the hotel and area! The only thing I was disappointed about was that the pool was freezing and hot tub was like warm. I’d go again nonetheless!!!!"
Stefana 4-night trip
Posted 10 hours ago
Holiday Inn Express St. Augustine near Dtwn - Historic by IHG

Find out more about Anastasia Island

Everything you need to know about Anastasia Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Anastasia Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anastasia Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Anastasia Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anastasia Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Anastasia Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Anastasia Island rentals

At Expedia, we put the best Anastasia Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Anastasia Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anastasia Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anastasia Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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