Anastasia Island Holiday Rentals

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Holiday 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 NZ$359
includes taxes & fees
27 May - 28 May
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, (84)
"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
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 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...
Ocean Village Club
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
Terrace/patio
The Dunes, Amazing 4 Bedroom, Ocean Front, Hot Tub, WIFI and more
7.0 out of 10, Good, (12)
"The location is what makes this place. The beach is a short up and over a single dune. Away from the more crowded public beach access points and easy walk to restaurants. The house is not luxurious but has all the essentials."
The Dunes, Amazing 4 Bedroom, Ocean Front, Hot Tub, WIFI and more
Beach
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
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
Interior
Beach Front+Heated Pool, SPA, Beach Views, Umbrella+Lounger forBeach, Balconies
9.8 out of 10, Exceptional, (145)
"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
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)
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
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⭐️
On the beach
Ocean View Unit 3305 - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]
10.0 out of 10, Exceptional, (121)
"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]
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
Fridge, microwave, oven, stovetop
Multi-Family Beach House w/Rooftop Ocean Views, 2 min. walk to Beach, Restaurants!
10.0 out of 10, Exceptional, (21)
"great location and house"
Multi-Family Beach House w/Rooftop Ocean Views, 2 min. walk to Beach, Restaurants!
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
On the beach
TIME TO BOOK FOR FAMILY SPRING AND SUMMER BEACH FUN!
9.8 out of 10, Exceptional, (69)
"The condo was as advertised. Everything from pots and pan's, linens, etc… were plentiful. Awesome place, would highly recommend!"
TIME TO BOOK FOR FAMILY SPRING AND SUMMER BEACH FUN!
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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, (2032)
"My daughter and I celebrated a late Mother's Day trip at Guy Harvey Resort. I planned to create a pro/con list for this review, but the visit was all pros! First of all, the stellar staff made our stay amazing. My daughter mentioned anyone who worked there seemed to actually like their job! They upgraded our room without hesitation, when they realized Expedia booked a standard instead of a partial view room. Then to our surprise, they had our room ready way before check in. (We were just gonna...
The price is NZ$291
includes taxes & fees
27 May - 28 May
Guy Harvey Resort on St Augustine Beach
Lobby lounge
Castillo Real Resort Hotel
3.0 star property
8.6 out of 10, Excellent, (1003)
"I stumbled upon this hotel because it was a great price for our week stay for our honeymoon, and I am more than happy I chose it. The staff was amazing, and the location is great. It’s only a 2 minute walk to the beach. They were under renovation, but it never bothered us. We were suppose to have a jacuzzi tub in our room, but we didn’t get it because of the remodel, which was totally fine. They gave us a discount for it not being exactly what we booked. The only thing I could even complain...
The price is NZ$259
includes taxes & fees
30 May - 31 May
Castillo Real Resort Hotel
Exterior
Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort
3.5 star property
8.8 out of 10, Excellent, (1003)
"Excellent services. The room was super clean and comfortable. The breakfast amazing! The only thing that we considered was to expensive was the valet parking... $39 per day tax it was a little too much."
The price is NZ$396
includes taxes & fees
29 May - 30 May
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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