Anastasia Island Holiday Rentals

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Holiday Rentals in Anastasia Island

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

9.8 out of 10, Exceptional, (59)
"Perfect place to stay "
Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants

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

10.0 out of 10, Exceptional, (106)
"Great vacation home for large family reunion! "
Waterfront home with dock, heated pool, & spectacular views- walk/bike downtown!

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

9.4 out of 10, Exceptional, (48)
"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!

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

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

10.0 out of 10, Exceptional, (120)
"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

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

Direct Oceanfront Condo W/ Large Balcony

9.8 out of 10, Exceptional, (210)
"Wonderful location close to anything you need.Beautiful beach. Didn’t want to leave!"
Direct Oceanfront Condo W/ Large Balcony

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

10.0 out of 10, Exceptional, (5)
Ocean View Condo - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]

Tidal Paradise - Heated Pool & Firepit! Walk to the Beach!

10.0 out of 10, Exceptional, (53)
"Could not have had a more perfect vacation. House and pool were just wonderful. 3 min drive to beach was so convenient. Will stay again and again!"
Tidal Paradise - Heated Pool & Firepit! Walk to the Beach!

You must have the experience, just steps from St Augustine's historic district

10.0 out of 10, Exceptional, (26)
"Everything was great"
You must have the experience, just steps from St Augustine's historic district

Cute 1 bedroom Oceanfront Condo- New Rental!

Cute 1 bedroom Oceanfront Condo- New Rental!

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

9.8 out of 10, Exceptional, (43)
"We had a fantastic trip. The house was conveniently located near the amphitheater, delicious restaurants and the beach. We couldn’t have asked for a better place to stay! "
Waterfront Retreat, Heated Pool & Rooftop Deck - 2 Bed, Kitchen, Great Location

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

9.6 out of 10, Exceptional, (136)
"The kitchen was well equipped and the whole house was comfortable with lots of beds. The beach was just to a short walk. We enjoy its pool and sauna.Thanks a lot. "
Ocean Breeze - Spacious Beach Home, Great for Family Vacation, Pool & Heated Spa

Direct Private Beach Access - Newly Renovated Condo - Heated Pool

9.4 out of 10, Exceptional, (77)
"Wonderful time, great condo!! Nice walk to the beach. "
Direct Private Beach Access - Newly Renovated Condo - Heated Pool

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

10.0 out of 10, Exceptional, (109)
"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!

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.

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

9.8 out of 10, Exceptional, (94)
"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

Atlantic View - Amazing Ocean Views, Pool and Heated Spa, Very Spacious Home

9.8 out of 10, Exceptional, (147)
"Awesome property. Close to the beach!"
Atlantic View - Amazing Ocean Views, Pool and Heated Spa, Very Spacious Home

Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable

10.0 out of 10, Exceptional, (7)
"Great location, very clean. Only issue was that the microfiber sheets were a little hot and scratchy. Otherwise a very comfy house and we really enjoyed our stay."
Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable

Crescent Sandpiper 214 OCEANFRONT -Oceanside pool Crescent Beach St Augustine

9.8 out of 10, Exceptional, (55)
"This place is just as described, great location and wonderful views. Ladonna thought of everything one would need to feel right at home. The bed was very comfortable. I haven’t had such a relaxing vacation in a long time. "
Crescent Sandpiper 214 OCEANFRONT -Oceanside pool Crescent Beach St Augustine
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, 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 favourite 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 depend 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 per night. Entering your travel dates in the search wizard might find you 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.