Anastasia Island Vacation Rentals

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Vacation Rentals in Anastasia Island

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!

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

9.8 out of 10, Exceptional, (58)
"Perfect place to stay "
The price is CA $136
CA $389 total
includes taxes & fees
Sep 18 - Sep 19
Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants

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, (119)
"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

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

10.0 out of 10, Exceptional, (105)
"Spring Break with our college age daughters. "
Waterfront home with dock, heated pool, & spectacular views- walk/bike downtown!

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!

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

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.

Captain's Oasis: Ocean View, Heated Pool, Putting Green, Walk to the Beach!

9.6 out of 10, Exceptional, (45)
"Beautiful location with plenty of fun activities for children!"
Captain's Oasis: Ocean View, Heated Pool, Putting Green, Walk to the Beach!

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 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]

Crescent Sandpiper 214 OCEANFRONT -Oceanside pool Crescent Beach St Augustine

9.8 out of 10, Exceptional, (54)
"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

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

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

10.0 out of 10, Exceptional, (25)
"Everything was great"
You must have the experience, just steps from St Augustine's historic district

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

10.0 out of 10, Exceptional, (8)
"This place is beautiful. We enjoyed watching the dolphins swim every day. It was a short distance to the beaches, shopping, and restaurants. We had an unexpected problem with the air conditioner but the hosts had a solution within hours. They were great to work with! "
Waterfront! Incredible Views, Watch the Dolphins Play, Perfect for Groups, $300 in Free Tickets!

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!

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

9.8 out of 10, Exceptional, (147)
"The property was amazing, the pool was incredible. Very clean and well decorated interior. Would highly recommend! And will definitely stay here again in the future "
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."
The price is CA $186
CA $537 total
includes taxes & fees
Sep 8 - Sep 9
Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable

Ocean View Unit 3305 - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]

10.0 out of 10, Exceptional, (160)
"Very happy with the property and with quick responses from owners! Very relaxing stay and would stay there again! "
Ocean View Unit 3305 - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]
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 vacation rentals

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

Anastasia Island vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anastasia Island vacation rentals we have selected for you start as low as CA $136 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 vacation 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 vacation.

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.