House vacation rentals in Anastasia Island

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Popular amenities for Anastasia Island house rentals

House rentals with a pool

Top guest favorite
Home in St. Augustine
4.97 out of 5 average rating, 72 reviews

Music on Marilyn- Steps from the Amp! ‱Jacuzzi‱

JasonRating, 5 stars5 days ago
Our family had a great time staying at this house. The kids loved the pool and game room. We loved the privacy of the house in a peaceful and quiet neighborhood. There were many good restaurants and things to do close by. Rachel responded very quickly to any questions we had. We would definitely stay here again.
Top guest favorite
Home in St. Augustine
4.99 out of 5 average rating, 412 reviews

Your Home Away From Home

ArleneRating, 5 stars5 days ago
This was our second visit to Fred and Lynn's home and it didn't disappoint. When visiting other home I have always taken my own pots and pans as I always encounter cheap thrift store cookware, but not here. I left my kitchen home this trip and it was great! We love how secluded and private it is. You would never know you are only 5 minutes away from shopping and grocery stores. Especially when the local deer herd visits in the early mornings and late afternoons. We plan on returning next summer! 😊
Top guest favorite
Home in St. Augustine
5 out of 5 average rating, 128 reviews

Private oasis, private pool, exceeds expectations

DonnaRating, 5 stars1 month ago
So relaxing In such a beautiful setting. Loved relaxing in the sun by the pool. Able to get fresh eggs every morning from the hens on the property who were always excited to see us. Wouldn’t hesitate to visit again and stay at the property.
Top guest favorite
Home in St. Augustine
4.93 out of 5 average rating, 118 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

KacieRating, 5 stars1 week ago
This place was amazing! Perfect location, only 15 minutes of St. George street. The pool was amazing and very refreshing! My dog absolutely loved the backyard. We even got to see a few deer! Very clean and the host is very responsive. My nephew loved the pool table! I would definitely recommend this location!
Top guest favorite
Home in St. Augustine
4.99 out of 5 average rating, 104 reviews

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach

JuliaRating, 5 stars1 week ago
We loved our stay at Whitney and John’s place! Their home was immaculate. Perfect for a baby and two young children and a dreamy retreat for the adults. Just a few minutes walk to the beach. Adorable restaurants also walkable and perfect for a family! Whitney and John were so lovely and responsive. We can’t wait to go back!
Superhost
Home in St. Augustine
4.85 out of 5 average rating, 47 reviews

Surf Break Lodge| Private Pool l Summer Discount

VanessaRating, 5 stars2 weeks ago
This house was great for our mini family getaway. Pros: location (one block to the beach and many restaurants), plenty of parking, clean space, comfortable beds, beautiful decor, private salt water pool with toys, washer and dryer with pods. Cons: limited towels- however host quickly responded and brought more, no toiletries (bring your own) light window coverings (bring sleep masks), TV stations can be limiting- best if you have your own streaming logins. Over all worth the price.
Top guest favorite
Home in St. Augustine
4.97 out of 5 average rating, 117 reviews

The Salty Seashell, Coastal Pool Home, Sleeps 8

BobRating, 5 stars2 weeks ago
We are finding it difficult to put into words just how enjoyable this entire experience was! The home and Stephenie's assistance throughout this trip was absolutely fantastic. The home is absolutely perfect - JUST what we needed....it felt like home - and Tammy, as a property manager for a large resort in Treasure Island, Florida, knows quite well how to take care of guests and the home she and her friends stayed at here met EVERY possible criteria. 5-Star is not even remotely good enough to describe it. Tammy and her husband plan on another trip later in the year and will cross their fingers that Stephenie's absolutely lovely home will be available. VERY DEFINITELY worth reaching out to Stephenie.....this is THE place to stay while visiting St. Augustine!!!!! With much gratitude, Tammy H.
Top guest favorite
Home in St. Augustine
4.99 out of 5 average rating, 146 reviews

4Bed, 3Bath-Heated Pool & SPA-Don't You Wanna?

KarenRating, 5 stars4 days ago
We had a fantastic vacation! The house was exactly as represented in the pictures. The living space was cozy and convenient for our multiple generations. The kitchen was well stocked with kitchen essentials as well as unexpected amenities like paper towels, trash bags, dish detergent, etc. The bedrooms were roomy and the beds comfortable. The 3 full baths were expertly updated. The putting green provided tons of family fun and the pool was cool and refreshing. We loved the convenience of available beach amenities (chairs, wagon, boogie boards) and found the short walk to the beach to be a great perk. We are definitely considering a return stay at “Don’t You Wanna”!

Weekly house rentals

Guest favorite
Home in St. Augustine
4.86 out of 5 average rating, 57 reviews

Bridgekeeper's Cottage

CrystalRating, 5 stars2 weeks ago
This home is so close to beach. The beach was not crowded at all. The home was relaxing and very clean. We enjoyed our stay.
Top guest favorite
Home in St. Augustine
5 out of 5 average rating, 8 reviews

Dolphins and Dream Water Views, Dock Your Boat!

JamieRating, 5 stars1 week ago
My family had a wonderful stay for our first time in the area. Most of our time at home was spent watching wildlife from the large porches in the mornings and evenings. We flew in with only carry-ons so the beach chairs, beach bag, towels, water toys were a huge bonus. The house truly has everything you need and a gorgeous view. We had two teenage boys who were in awe of the inlet area watching high/low tide changes and checking out the river wildlife with kayaks - it's a very special place.
Top guest favorite
Home in St. Augustine
4.93 out of 5 average rating, 58 reviews

The Waterfront Retreat with Inlet view & parking

JeanieRating, 5 stars2 months ago
Great location, lovely view and cozy beds. Do note, the stairs that give you that great view might be a bit of a challenge for some. Nice natural light and a good open kitchen to enjoy friends. Hope to stay again!
Top guest favorite
Home in St. Augustine
5 out of 5 average rating, 26 reviews

4BR, Dog Friendly Home Away from Home on the Beach

NathanaelRating, 5 stars1 week ago
We had an incredible stay at this home in St Augustine! Johanna was an excellent host who communicated everything so timely and even offered us early check-in, which was a nice surprise. Once you enter the home, you can tell how much thought went into everything. It's a perfect place for families and very toddler-friendly with tons of toys for the little ones to play with. Most of all, the house is really beautiful and clean, and it's very well priced for how much space you get. It worked out so well for our annual family trip. Thanks to Johanna for making it amazing! Would highly recommend.
Top guest favorite
Home in St. Augustine
5 out of 5 average rating, 87 reviews

Luxury Modern Home in Prime Location 2BDR-3BTH

JarredRating, 5 stars3 days ago
My family and I had a great experience staying here! The place was clean, comfortable, and exactly as described. The host was friendly and responsive, which made everything smooth and stress-free. I’d definitely recommend it and would love to stay again in the future!
Superhost
Home in St. Augustine
5 out of 5 average rating, 3 reviews

Pre-Reno Sale, EV Charger, 3 min to beach, Dogs OK

AmyRating, 5 stars1 month ago
The property was top notch! Extremely clean & comfortable / lots of room & relaxing! It was a short driving distance to whatever you might want to do. Host had lots of local recommendations which was super insightful & appreciated!
Guest favorite
Home in St. Augustine
5 out of 5 average rating, 16 reviews

New Lux Rental, Walk to Downtown

AmaniRating, 5 stars2 weeks ago
Location is perfect for exploring the historic district of St. Augustine. The place is very chic/clean and the surrounding neighborhood is very quiet and friendly. My family and I really enjoyed the fact that Cornerstone Cafe was a super short walk from the house (their breakfast and coffee was very delicious). The host was very hospitable and helpful. Would definitely recommend!
Guest favorite
Home in St. Augustine
4.94 out of 5 average rating, 18 reviews

E Street Palace-Modern Pool Home

LorraineRating, 5 stars2 weeks ago
Our family gathering was great. Everyone enjoyed the amenities and the space. The privacy of having two separate Spaces within one was also a plus with the two kitchens. We enjoyed ourselves immensely and would highly recommend this property as a great getaway.

Private house rentals

Guest favorite
Home in St. Augustine
4.95 out of 5 average rating, 20 reviews

Whole House Not Shared, Private in St Augustine FL

CalebRating, 5 stars1 month ago
My FiancĂ©e and I visited Matt’s house to celebrate my graduation. The house was not only easy to find, but was in a very inviting and vibrant neighborhood. The house itself was perfect for the stay, nothing too big or too small, with a quick and easy drive to downtown, and all the beaches you could ask for. The only suggestion I would add is a microwave would be a good addition, but outside of that, we had a blast with not only the destination, but also the house!
Top guest favorite
Home in St. Augustine
4.95 out of 5 average rating, 38 reviews

Heated Saltwater Pool|Walk to Beach|Dogs Welcome!

JonathanRating, 5 stars1 week ago
St. Augustine has been our go to beach destination the last few years and this home has been our favorite so far. It had everything we wanted - private swimming pool, easy beach access, and a place to go fishing. Access to the beach was just a short walk (maybe 7 -8 minutes). You have to cross A1A but it was never an issue as there is a pedestrian crosswalk. We really enjoyed the pool. It is a good size and heated so the temperature was always perfect both during the day and evening. All outdoor furniture was in excellent shape and very comfortable. The gas grill looked almost new and was fully functional. The home backs up to a canal which connects to the Matanzas River. I was able to catch a couple of fish from the backyard and probably could have caught more if I was more diligent. The inside of the home was spotless clean and nicely decorated. The kitchen was fully stocked with decent quality cookware. We also really enjoyed the pool table. The hosts were very responsive
Top guest favorite
Home in St. Augustine
4.99 out of 5 average rating, 96 reviews

Beach Getaway - Upstairs

AlexRating, 5 stars1 week ago
Beautiful and quiet place to hang out for a few days, just minutes from the beach. Close to delicious restaurants. Maya's place was very clean. I recommend it and would stay again in a heartbeat.
Guest favorite
Home in St. Augustine
4.93 out of 5 average rating, 61 reviews

Elevated Beach Haus

BrooklynRating, 5 stars1 week ago
I LOVED that everything in the house was labeled. It’s such a relaxing little house and I already want to come back.
Top guest favorite
Home in St. Augustine
5 out of 5 average rating, 25 reviews

Brand New & open for Summer! 5 min. Bike to Beach!

EricRating, 5 stars3 weeks ago
Exceptionally clean and nicely designed fresh home very close to Crescent Beach and Historic St. Augustine. Perfect for beach getaway and short drive from many bars and restaurants. Great host who made everything simple and provided local recommendations. Highly recommend, short drive to three beach areas.
Guest favorite
Home in St. Augustine
4.86 out of 5 average rating, 35 reviews

Seas the Day € 3 Mins to Beach!

WendyRating, 5 stars1 week ago
Had a great time with it being our first time to St. Augustine. The house was beautiful and not far from the beach either. Well worth it.
Superhost
Home in St. Augustine
4.76 out of 5 average rating, 67 reviews

Oceanfront Sun & Fun @ Saint Augustine Beach!

AllisonRating, 5 stars2 weeks ago
We loved staying at JP's place! The location cannot be beat -- the entrance to the beach is basically in the backyard. The beach itself is beautiful, and was not crowded. Walkable to great restaurants and coffee. Really appreciated all the recommendations in the house guide! I ordered Instacart for groceries and they came within 30 mins. A quick 10 min drive into the heart of St. Augustine. The house is cute and nicely decorated, everything was very clean (it's a beach house so obviously sand still makes its way in). We stayed very comfortably with our family of 4 (2 kids) + my mom (grandma), and hope to stay again!
Top guest favorite
Home in St. Augustine
4.97 out of 5 average rating, 79 reviews

Island Breeze - Screened Lanai/Pool/Close to Beach

marionRating, 5 stars3 weeks ago
Pure delight in such a lovely setting! Tropical, lush clean landscape, delightful pool so relaxing and just the right size. The lanai patio was screened in , watching TV with coffee in the AM perfect. Comfy beds, nice linens, lots of space, workable pretty kitchen, outdoor shower so convenient, the tv has good choices, the grill so nice to cook on, we were amazed at the accuracy of the position of the dishwasher! Lol YOU HAVE TO STAY HERE! A short pretty walk to the vast huge beach, so nice to do what you want there, no restrictions, dogs, tents, cigars, food, drinks, you can walk for miles and the shells are fun. Thank you for a perfect BIRTHDAY getaway xo.

Destinations to explore

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