Holiday Rentals in Anastasia Island

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Anastasia Island

1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24
9.6 out of 10, Exceptional, 137 reviews
"A really nice comfortable place to stay with easy access to the beach. The place had all the conveniences of home. The host was very accommodating and responsive to all our questions during our stay. Had all the conveniences that you would need."
The price is €207
includes taxes & fees
6 Jun - 7 Jun
1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24
Steps to Beach! Newly Renovated w/Sunroom, En-suite Bedrooms, Walk to Restaurants, Shops, Ocean Pier
9.8 out of 10, Exceptional, 85 reviews
"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
St Augustine Beach Condo just steps from the beach!
10.0 out of 10, Exceptional, 28 reviews
"Sleep quality was 0. Everything else was fine."
St Augustine Beach Condo just steps from the beach!
Save an average of 15% on thousands of hotels when you're signed in
Ocean Gate at Hibiscus Resort
4.0 star property
8.8 out of 10, Excellent, 108 reviews
"Everything was awesome "
Ocean Gate at Hibiscus Resort
Ocean Village Club
3.0 star property
8.6 out of 10, Excellent, 31 reviews
"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 €745
includes taxes & fees
20 Jun - 21 Jun
Ocean Village Club
Enjoy ocean sunrises on beautiful Anistasia Island as well as oldest city in USA
9.0 out of 10, Wonderful, 30 reviews
"The place was perfect and so was the location. I think the cleaning service dropped the ball, we took the first few hours to clean the place ourselves. That was the only hickup. The place was roomy, had everything you can ask for, the beach entrance is on the property, pool was across from the rental, restaurants in walking distance, putt putt in walking distance, classy people all around. I would buy this property if I could. Highly recommend."
Enjoy ocean sunrises on beautiful Anistasia Island as well as oldest city in USA
Blue Heron - Amazing Backyard and Heated Pool, Near Beach & Historic Downtown
10.0 out of 10, Exceptional, 36 reviews
"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
The Dunes, Amazing 4 Bedroom, Ocean Front, Hot Tub, WIFI and more
7.0 out of 10, Good, 12 reviews
"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
Spacious Beach Townhome ~ Pet Friendly ~ Great Price
9.6 out of 10, Exceptional, 53 reviews
"The townhouse was clean, comfortable and nicely decorated. It was Short walk to the beach which was wonderful. We enjoyed our stay and wild definitely book it again."
Spacious Beach Townhome ~ Pet Friendly ~ Great Price
Ocean View Unit 3305 - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]
10.0 out of 10, Exceptional, 124 reviews
"This was a perfect place for us, 2 adults and 2 teenagers. It was close to the beach. You can even see the ocean from the balcony. The beds were comfortable and the place was clean. There was plenty of room for all of us. Thank you for a great stay!"
Ocean View Unit 3305 - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]
Ocean Cottage Steps from Sand and HEATED Pool, Private Access, Deck w/Grill, Walk to Restaurants
10.0 out of 10, Exceptional, 19 reviews
"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
Relaxed Cancellation Policy! Oceanfront home with pool,hot tub, fire pit, bikes.
9.6 out of 10, Exceptional, 113 reviews
"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.
Brand New Condo w/Beach View, Easy Walk to Beach, Restaurants, Coffee Shops, Ocean Pier, Bars, Grill
10.0 out of 10, Exceptional, 45 reviews
"We had a great time during our stay. The place was very clean and cozy, and it was just a very short walk to the beach. We loved watching the sunrise, walking to the coffee shop in the mornings, and having dinner in the evenings. Historical St. Augustine is just a quick 10-15 minute drive away. We also enjoyed Beachside Diner for breakfast, which is conveniently located across the street. I highly recommend this place! We will be returning!"
Brand New Condo w/Beach View, Easy Walk to Beach, Restaurants, Coffee Shops, Ocean Pier, Bars, Grill
Sand pail Beach Cottage🏖️-new 3+/2.5 house- steps to the beach-private pool- 5⭐️
10.0 out of 10, Exceptional, 35 reviews
"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⭐️
Beach Front+Heated Pool, SPA, Beach Views, Umbrella+Lounger forBeach, Balconies
9.8 out of 10, Exceptional, 145 reviews
"The house is great and the pictures represent the house and the view well. We had a wonderful time and the host was fantastic and super responsive when we had questions. Two "good to know" points I think should be made that I do not believe are listed in the description-- 1) The house is on a part of the beach that cars can drive on. You CANNOT see or hear the cars from the property- but it would have been nice to know. 2) There is construction on the house next door. We rarely heard anything-...
Beach Front+Heated Pool, SPA, Beach Views, Umbrella+Lounger forBeach, Balconies
Classic Oceanfront cottage with yard and beach access in St. Augustine Beach
10.0 out of 10, Exceptional, 20 reviews
"The cottage was perfect for our family! Walked back & forth to the beach with ease & felt like we had our very own walkway! Would love to be able to sit in house & see the water but I understand the importance of the dunes. Maybe a rooftop porch in the future? This house was equipped with absolutely everything we needed!"
Classic Oceanfront cottage with yard and beach access in St. Augustine Beach
Ocean front property 2 bedroom cottage steps to ocean (Surf Crest Village #23)
9.6 out of 10, Exceptional, 85 reviews
"Great stay!"
Ocean front property 2 bedroom cottage steps to ocean (Surf Crest Village #23)
Ocean Song - 5 Star Ocean View Beach Side
10.0 out of 10, Exceptional, 157 reviews
"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
La Sirenita Hideaway Beach House
8.8 out of 10, Excellent, 5 reviews
"It was a perfect spot for a girls trip to St Augustine!"
La Sirenita Hideaway Beach House
Oceanfront, dog-friendly home with screened lanai, beach walkway & fast WiFi
8.2 out of 10, Very good, 35 reviews
"We had a great time with our family of 4 at this home. It is a smaller home on the block, so would not be good for more than 4-6 people. The private pool is fantastic, the heater was turned on for us on arrival (i did call to confirm many times). The home was very clean when we arrived. The walk to the beach is beautiful through the marsh. You cannot take a wagon through this area as there is a lot of hills and decking fyi. But it is close enough to bring just a few things, very close. To be...
Oceanfront, dog-friendly home with screened lanai, beach walkway & fast WiFi
Don't see what you're looking for?
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

Guy Harvey Resort on St Augustine Beach
3.0 star property
8.4 out of 10, Very good, 2,060 reviews
"This hotel was perfect for our vacation to St. Augustine. The pool and tiki bar was perfect end to everyday, and the proximity to the beach was great. The laid back vibe was just what we were looking for. This place is also perfect for people traveling with pets. "
The price is €163
includes taxes & fees
5 Jun - 6 Jun
Guy Harvey Resort on St Augustine Beach
Castillo Real Resort Hotel
3.0 star property
8.6 out of 10, Excellent, 1,000 reviews
"Nice hotel! Great access to beach!"
The price is €145
includes taxes & fees
12 Jun - 13 Jun
Castillo Real Resort Hotel
Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort
3.5 star property
8.8 out of 10, Excellent, 1,000 reviews
"Great staff & beautiful atmosphere!"
The price is €248
includes taxes & fees
13 Jun - 14 Jun
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anastasia Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Anastasia Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anastasia Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anastasia Island holiday rentals we have selected for you start as low as €207 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Anastasia Island rentals

At Expedia, we put the best Anastasia Island holiday 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 holiday.

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