Anastasia Island Vacation Rentals

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Vacation Rentals in Anastasia Island

Beach nearby, sun loungers, beach towels
1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24
9.6 out of 10, Exceptional, (136)
"Everything was perfect. We hope to go back soon"
The price is $79
$219 total
includes taxes & fees
May 30 - May 31
1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24
3 outdoor pools
Ocean Gate at Hibiscus Resort
4.0 star property
8.8 out of 10, Excellent, (108)
"Everything was awesome "
Ocean Gate at Hibiscus Resort
Beach nearby
Steps to Beach! Newly Renovated w/Sunroom, En-suite Bedrooms, Walk to Restaurants, Shops, Ocean Pier
9.8 out of 10, Exceptional, (85)
"This property was the best! We had a great 5 nights as a family of 4. You can walk to everything - the beach, amazing restaurants, coffee shop, donuts, ice cream, the pier, etc! The house was comfortably ready for us, super clean and well stocked. We REALLY appreciated the beach toys, chairs & umbrella! Cannot wait to return! 5 🌟"
Steps to Beach! Newly Renovated w/Sunroom, En-suite Bedrooms, Walk to Restaurants, Shops, Ocean Pier
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Property grounds
Blue Heron - Amazing Backyard and Heated Pool, Near Beach & Historic Downtown
10.0 out of 10, Exceptional, (36)
"There were 5 of us all in our early 60s. There was so much room in this house! Big kitchen and 2 living room areas. Great master bed and bath. The backyard was the gem of this property. Pool and outdoor cabana were perfect to spend a hot day lounging around the pool. Lots of shade if you need it. Location of the house is perfect! You could walk across the Bridge of Lyons to the historic district. The host was very responsive to our quick questions. We will definitely be back!"
Blue Heron - Amazing Backyard and Heated Pool, Near Beach & Historic Downtown
Fridge, microwave, oven, stovetop
Enjoy ocean sunrises on beautiful Anistasia Island as well as oldest city in USA
9.0 out of 10, Wonderful, (28)
"Overall a very comfortable condo. We have stayed in this complex several times. Would have been nice to have chairs that are appropriate for relaxing on the beach. Will definitely consider staying here on a future trip!!"
Enjoy ocean sunrises on beautiful Anistasia Island as well as oldest city in USA
View from property
Relaxed Cancellation Policy! Oceanfront home with pool,hot tub, fire pit, bikes.
9.6 out of 10, Exceptional, (113)
"We were very pleased with booking process and the property manager communication gave us confident we made a good choice. We greatly enjoyed our stay on St Augustine Beach and the oceanfront location of this property!"
Relaxed Cancellation Policy! Oceanfront home with pool,hot tub, fire pit, bikes.
Beach | On the beach, sun loungers, beach towels
St Augustine Beach Condo just steps from the beach!
10.0 out of 10, Exceptional, (27)
"Clean well stocked first floor condo close to beach walk over. Mike the owner was easy to message and replied quickly. Highly recommend."
St Augustine Beach Condo just steps from the beach!
Beach nearby
Ocean Village Club
3.0 star property
8.6 out of 10, Excellent, (30)
"The property is very nice and overall well-maintained. Just a few minor details keep me from giving 5 stars. 1. Access directions are accurate but could be made better by explaining how to get the gate key first (it’s kept off-site) and then how to get in the room 2) Basic supplies given are minimal at best. One roll of toilet paper for each bathroom is just not enough. Also only one trash bag given and absolutely no simple condiments like salt and pepper. These are items you shouldn’t have to...
The price is $153
$780 total
includes taxes & fees
May 31 - Jun 1
Ocean Village Club
Beach nearby
Ocean Cottage Steps from Sand and HEATED Pool, Private Access, Deck w/Grill, Walk to Restaurants
10.0 out of 10, Exceptional, (19)
"Awesome stay. So close to Beach and local activities. Can't wait to get back."
Ocean Cottage Steps from Sand and HEATED Pool, Private Access, Deck w/Grill, Walk to Restaurants
Beach | Beach nearby
Spacious Beach Townhome ~ Pet Friendly ~ Great Price
9.6 out of 10, Exceptional, (52)
"Beautiful and perfect location."
Spacious Beach Townhome ~ Pet Friendly ~ Great Price
Outdoor pool, a heated pool
Ocean Front Condo With Heated Pool outdoor patio overlooking the Ocean
9.2 out of 10, Wonderful, (88)
"Everyone wants different things...i wanted to be able to have a short walk to the beach, to see the ocean from the condo, and a pool in case the weather prevented swimming in the ocean for my girlfriend's 50th. Check, check, check. And that's harder to find than you'd think! Add in a very responsive host and a smooth check-in process (dont forget to use the code on the lock box, not the code panel), and this place is really hard to beat. We'll be back, for sure, the next time we're in the area....
Ocean Front Condo With Heated Pool outdoor patio overlooking the Ocean
On the beach
Ocean View Unit 3305 - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]
10.0 out of 10, Exceptional, (122)
"We really liked the location of the place. It was just a few minute walk to a stunning beach that we walked and swam in every morning. The apartment was spacious, with 3 tv’s 1 in the living room and 1 in each bedroom. The host was very responsive. We would go stay another time for sure."
Ocean View Unit 3305 - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]
Terrace/patio
The Dunes, Amazing 4 Bedroom, Ocean Front, Hot Tub, WIFI and more
7.0 out of 10, Good, (12)
"I wanted to give an honest review of this house for the price I paid. I stayed here with my family with four children. I’ll start with the positives…. This is a beautiful and easy access location if you have children. Going over the dune is very easy but coming up is a little more difficult because it’s steep but it’s super easy to leave your things on the beach in order to eat lunch at the house or let the kids nap and return to the beach. I also enjoyed the back yard and my kids being able to...
The Dunes, Amazing 4 Bedroom, Ocean Front, Hot Tub, WIFI and more
Fridge, microwave, oven, stovetop
Ocean front property 2 bedroom cottage steps to ocean (Surf Crest Village #23)
9.6 out of 10, Exceptional, (83)
"Total relaxation with an "Old Florida" vibe. Patty & Harry are great. 2nd stay, will be back for a 3rd."
Ocean front property 2 bedroom cottage steps to ocean (Surf Crest Village #23)
Outdoor pool, a heated pool
Sand pail Beach Cottage🏖️-new 3+/2.5 house- steps to the beach-private pool- 5⭐️
10.0 out of 10, Exceptional, (35)
"Great house in great location! Kids enjoyed the pool each day and the easy walk to the beach and beautiful walkable beach. We love St. Aug beach!"
Sand pail Beach Cottage🏖️-new 3+/2.5 house- steps to the beach-private pool- 5⭐️
Fridge, microwave, oven, dishwasher
Classic Oceanfront cottage with yard and beach access in St. Augustine Beach
10.0 out of 10, Exceptional, (19)
"We really enjoyed the sea shell cottage, it is so close to the beach and had everything our family needed to enjoy our visit to St. Augustine. The cottage was clean and stocked with towels and linens. We will definitely be rebooking!"
Classic Oceanfront cottage with yard and beach access in St. Augustine Beach
Beach nearby
Ocean Song - 5 Star Ocean View Beach Side
10.0 out of 10, Exceptional, (157)
"My daughter and I stayed at ocean song for Mother’s Day weekend. We had a really good time. Place was extremely clean, (I think this was the first time I didn’t have to clean anything when I got to a vacation house), close to the beach and it was very relaxing sitting outside on the deck at night, listening to the ocean. We will definitely stay again!"
Ocean Song - 5 Star Ocean View Beach Side
Property grounds
Bright 1940s beach cottage with cabana plus private pool
9.4 out of 10, Exceptional, (103)
"Everything was as good or better than expected. Highly recommend."
Bright 1940s beach cottage with cabana plus private pool
Pool | Outdoor pool, a heated pool
Villa Elena - Elegant Spacious House by the Beach with Large Pool & Heated Spa!
9.4 out of 10, Exceptional, (195)
"We had a wonderful, relaxing stay in this great home. Our family of 5 adults and 2 kids had plenty of room. David is a very responsive host. We had a couple of questions and he responded immediately. We will definitely plan a return trip in the future. Home is very close to the beach and many restaurants. A short trip to downtown Old St. Augustine."
Villa Elena - Elegant Spacious House by the Beach with Large Pool & Heated Spa!
On the beach
TIME TO BOOK FOR FAMILY SPRING AND SUMMER BEACH FUN!
9.8 out of 10, Exceptional, (70)
"Wonderful location, beautiful beach, and beautifully maintained landscaping of property. A quiet, relaxing stay. Highly recommend."
TIME TO BOOK FOR FAMILY SPRING AND SUMMER BEACH FUN!
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See all available properties in Anastasia Island
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.

Other types of properties in Anastasia Island you may be interested in

View from property
Guy Harvey Resort on St Augustine Beach
3.0 star property
8.4 out of 10, Very Good, (2046)
"It was the perfect place, great location, beautiful beach, quiet and refreshing pool!! "
The price is $159
$177 total
includes taxes & fees
May 28 - May 29
Guy Harvey Resort on St Augustine Beach
Lobby lounge
Castillo Real Resort Hotel
3.0 star property
8.6 out of 10, Excellent, (1007)
"The staff Rhonda and Darren were a great help and always so nice. The room was comfortable. The hot tub wasn't working but we enjoyed our stay."
The price is $119
$133 total
includes taxes & fees
Jun 11 - Jun 12
Castillo Real Resort Hotel
Exterior
Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort
3.5 star property
8.8 out of 10, Excellent, (1010)
"Beautiful, clean, comfortable, the staff were amazing. I will be returning"
The price is $237
$289 total
includes taxes & fees
Jun 2 - Jun 3
Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort
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.

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 $79 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.

Recent reviews of Anastasia Island properties
Expedia verified reviews

Ocean Breeze Inn

Ocean Breeze Inn

5/5 Excellent
"Nice and clean!! Fun atmosphere at the pier!! Good value "
A verified traveler stayed at Ocean Breeze Inn
Posted 1 day ago
Ocean Breeze Inn