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Top Holiday Rentals in Anastasia Island

Our top choices for Anastasia Island holiday rentals

9BR OCEANFRONT ESTATE! SWEEPING VIEWS, VERY LARGE POOL/YARD, COMPLETE GAME ROOM!

10.0 out of 10, Exceptional, (107)
"The property is amazing!!! Very clean, well-equipped kitchen, amazing views, great pool, access to beach was great and lots of beach accessories. Kelley was easy to deal with and very responsive to any questions I may have had. I would highly recommend staying here. "
9BR OCEANFRONT ESTATE! SWEEPING VIEWS, VERY LARGE POOL/YARD, COMPLETE GAME ROOM!

1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24

9.6 out of 10, Exceptional, (176)
"Just absolutely perfect everything was great."
The price is £181
includes taxes & fees
5 Sept - 6 Sept
1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24

Ocean View Condo - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]

10.0 out of 10, Exceptional, (3)
"Excellent property and host, most well supplied place we have stayed in a long time. Cloae easy walk to the beach."
Ocean View Condo - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]

Walk to Nights of Lights- Lovely 2 Bedroom-1 Bath Excellent location.

10.0 out of 10, Exceptional, (81)
"Large, soft memory foam bed, comfy large couch and a well-stocked kitchen made our month long stay enjoyable as we explored the area."
Walk to Nights of Lights- Lovely 2 Bedroom-1 Bath Excellent location.

Island Luxury and Location! Walk to downtown...Nights of Lights

10.0 out of 10, Exceptional, (118)
"Beautiful quite place away from busy of St Augustine, yet still walking distance. Highly recommend this place. "
Island Luxury and Location! Walk to downtown...Nights of Lights

Two pools - oceanfront! Luxury beachfront rental, stocked like your home

10.0 out of 10, Exceptional, (104)
"Great stay"
Two pools - oceanfront! Luxury beachfront rental, stocked like your home

Waterfront! Incredible Views, Watch the Dolphins Play, Perfect for Groups, $300 in Free Tickets!

10.0 out of 10, Exceptional, (8)
"I wish I could rate it 10 stars. The host was amazing and responded so fast to every question I had. The house is WAY bigger in person than it looks in the photos. They left us treats at check in that were delicious. The location is amazing, so perfect to sit on the huge balcony and watch the sun rise over the ocean! Great place and we will definitely come back. Highly recommend! "
Waterfront! Incredible Views, Watch the Dolphins Play, Perfect for Groups, $300 in Free Tickets!

Sun & Fun @ Can't Be Beat Beachfront Location!

9.4 out of 10, Exceptional, (46)
"Location is King! We loved the easy walk to the beach and proximity to historic downtown St. Augustine! "
Sun & Fun @ Can't Be Beat Beachfront Location!

Steps to Sand, HEATED Pool, Private Access, Deck, Grill, Walk to Restaurants, $300 in Free Tickets!

10.0 out of 10, Exceptional, (42)
"Great place with a great price we could not have asked for a better vacation."
Steps to Sand, HEATED Pool, Private Access, Deck, Grill, Walk to Restaurants, $300 in Free Tickets!

Stunning 2/2 beach duplex condo only steps away from ocean!!

9.6 out of 10, Exceptional, (73)
"We loved staying at this condo which was a short walk to the beach and pool. It had all of the amenities from the listing and more. The host was easy to work with and we would definitely stay here again! "
Stunning 2/2 beach duplex condo only steps away from ocean!!

Multi-Family Beach House, Ocean Views, 2 min Walk to Beach, Restaurants, Shops! $300 in Free Tickets

9.6 out of 10, Exceptional, (50)
"Location was great, communication with the manager was easy and the house worked well for our multiple families. We would book here again!"
Multi-Family Beach House, Ocean Views, 2 min Walk to Beach, Restaurants, Shops! $300 in Free Tickets

Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants

9.8 out of 10, Exceptional, (57)
"Perfect place to stay "
The price is £214
includes taxes & fees
18 Sept - 19 Sept
Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants

Blue Heron - Amazing Backyard and Heated Pool, Near Beach & Historic Downtown

9.8 out of 10, Exceptional, (92)
"This is definitely going to be a regular spot for our family when we need a staycation in St. Augustine. The backyard and pool area is amazing and the house was perfect for us. Great time was had over our weekend at the property."
Blue Heron - Amazing Backyard and Heated Pool, Near Beach & Historic Downtown

Waterfront home with dock, heated pool, & spectacular views- walk/bike downtown!

10.0 out of 10, Exceptional, (103)
"Spring Break with our college age daughters. "
Waterfront home with dock, heated pool, & spectacular views- walk/bike downtown!

Starfish - Heated Pool & King Beds! Near: Amphitheatre, Historic Downtown, Beach

9.6 out of 10, Exceptional, (135)
"We loved our stay here and the hosts were so kind! Lovely property, would definitely stay here again :)"
Starfish - Heated Pool & King Beds! Near: Amphitheatre, Historic Downtown, Beach

Ocean Breeze - Spacious Beach Home, Great for Family Vacation, Pool & Heated Spa

9.6 out of 10, Exceptional, (136)
"10 family members met at your VRBO house and had a great long weekend of family fun! The property owner was very responsive to our inquiries and made sure we had answers to all our questions. "
Ocean Breeze - Spacious Beach Home, Great for Family Vacation, Pool & Heated Spa

Waterfront Retreat, Heated Pool & Rooftop Deck - 2 Bed, Kitchen, Great Location

9.8 out of 10, Exceptional, (43)
"This was such a great place and kid friendly and so close to everything! It was actually sad to leave. We will be back "
Waterfront Retreat, Heated Pool & Rooftop Deck - 2 Bed, Kitchen, Great Location

Ocean Gate at Hibiscus Resort

4.0 star property
8.6 out of 10, Excellent, (126)
"Stayed here for a week with my family and we had a great time. Great location and all of the amenities we needed. Only thing missing was beach chairs but we made do. "
Ocean Gate at Hibiscus Resort

Beach Front,Heated Pool,Spa, Beach Views, Umbrella+Lounger for beach, Balconies

9.8 out of 10, Exceptional, (160)
"Great stay for the Players Tournament "
Beach Front,Heated Pool,Spa, Beach Views, Umbrella+Lounger for beach, Balconies

APRIL DISCOUNT! Coquina Cove Heated Pool Home by Beach & Downtown

9.2 out of 10, Wonderful, (86)
"The property was clean and perfect for two families with four kids. Everyone had plenty of space and the kids loved playing in the heated pool. The host was very kind and easy to communicate with. In addition, the location was convenient being minutes from Historic St. Augustine and equally close to the beach. We had a great stay! "
APRIL DISCOUNT! Coquina Cove Heated Pool Home by Beach & Downtown
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

Find out more about Anastasia Island

Find out more about Anastasia Island

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 £181 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.