Anastasia Island Holiday Rentals

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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 NZ$397
per night
19 Jun - 20 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, 86 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!
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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 NZ$931
per night
22 Jun - 23 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, 46 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, 36 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
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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

Guy Harvey Resort on St Augustine Beach
3.0 star property
8.4 out of 10, Very good, 2,071 reviews
"Nicely updated hotel right on the beach. On-property restaurant was well priced with good food, and the restaurant staff were super friendly. Considering it’s a beach hotel that allows pets (and there were a lot of guests with dogs while we were there), they’ve done a really great job keeping the place clean. Made for a great beach weekend with the kids. "
The price is NZ$322
per night
9 Jun - 10 Jun
Guy Harvey Resort on St Augustine Beach
Castillo Real Resort Hotel
3.0 star property
8.6 out of 10, Excellent, 1,004 reviews
"Staff was very attentive and accommodating. I will definitely be staying here again on my next visit."
The price is NZ$255
per night
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, 1,004 reviews
"Everything was pretty amazing, just like the pictures. The only thing I would change was the smell on the room 253. Something was pretty smelly on the disposal and the maintenance wasn’t able to fix that during our stay. The breakfast is amazing and I would like to send a huge appreciation for the elderly man who works pretty hard everyday and made us feel cared."
The price is NZ$405
per night
24 Jun - 25 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.

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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