House vacation rentals in Anastasia Island

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Popular amenities for Anastasia Island house rentals

House rentals with a pool

Guest favorite

Home in Palm Coast

4.91 out of 5 average rating, 177 reviews

Spacious Heated Pool home with pool/pingpong table

JodiRating, 5 stars2 weeks ago
The house was lovely, clean, inviting and spacious. My only complaint was Florida had unseasonably cold weather the weekend we were in town and we weren't able to get in the pool!! I will recommend the home to friends!
Guest favorite

Home in St. Augustine

4.96 out of 5 average rating, 101 reviews

New luxury heated pool home steps from the beach!

GeneRating, 5 stars4 weeks ago
This is a great place with the quick access to the beach and 15 minutes driving to the center of the st. Augustine. The pool is heated and kids were very happy to play there. The house has everything you need in plenty. Definitely recommend.
Superhost

Home in St. Augustine

4.92 out of 5 average rating, 125 reviews

steps to the beach, double mastersuite- pool home

CherieRating, 5 stars1 month ago
We had such a fun stay! The home was beautiful, well stocked and very comfortable. The Christmas tree was a special touch! We enjoyed being so close to the beach! We also really enjoyed the Nights of Lights in St. Augustine. We would highly recommend staying here!
Guest favorite

Home in St. Augustine

4.98 out of 5 average rating, 157 reviews

Historic St. Augustine 2/2 Duplex & Pool

ChristinaRating, 5 stars2 weeks ago
Lili was a wondeful host. Her home exceeded our expectations. Walking distance to the historic district and restaurants and a perfect place to relax during down time. We will definitely be booking with Lili again. Highly recommend.
Guest favorite

Home in St. Augustine

5 out of 5 average rating, 136 reviews

Southern Charmer w/Pool - Walk to Everything!

CheriRating, 5 stars1 week ago
My husband, little dog, and I loved the Southern Charmer! It was a great place to celebrate my husband’s birthday. We stayed at Pauline’s house next door last year for my birthday and I had stayed there another time with my husband’s sisters. Both houses are great and the location cannot be beat. Close to downtown but in a quiet residential area so it is very peaceful. The views from the Southern Charmer are beautiful. Pauline is a great host. Super responsive and accommodating.
Guest favorite

Home in St. Augustine

4.96 out of 5 average rating, 184 reviews

Walk downtown to see nights of lights, heated pool

ClaudetteRating, 5 stars3 weeks ago
Short notice and everything was just perfect. I would definitely stay here again and highly recommend this house!
Guest favorite

Home in St. Augustine

4.84 out of 5 average rating, 208 reviews

Spacious St. Augustine Home "The Gold Knocker"

JaredRating, 5 stars2 weeks ago
Nicky was a fabulous host. The house was extremely clean. She was also very responsive and accommodating! Highly recommended.
Superhost

Home in St. Augustine

4.86 out of 5 average rating, 114 reviews

Best of Both Worlds- Family Oasis

GreysonRating, 5 stars1 week ago
We enjoyed our stay at Lindsay’s place! It was exactly as listed and a great location, which was a quick walk across the bridge to the downtown area. The backyard area and hot tub were a nice bonus.

Weekly house rentals

Guest favorite

Home in St. Augustine

4.75 out of 5 average rating, 106 reviews

On the Canal, by Beach, Kayaks, Dock, Fishing

JohnRating, 5 stars3 months ago
Great stay & will happily return. The house was super clean & in a very quiet location. We enjoyed the outdoor space, it was so peaceful. The beds were comfortable, the kitchen had everything & then some. Easy walk to the beach & short drive to all St Augustine has to offer. Thanks for hosting us!
Superhost

Home in Palm Coast

5 out of 5 average rating, 5 reviews

Suburban paradise

SandyRating, 5 stars2 months ago
We had a wonderful Thanksgiving here with very roomy and comfortable. Would definitely stay here again .
Guest favorite

Home in St. Augustine

5 out of 5 average rating, 31 reviews

5BR, Pool,HotTub, Putput, Walk to Beach,Game RM!

BrunoRating, 5 stars1 month ago
What a wonderful home to celebrate Christmas! A beautiful home… all the amenities… heated pool… cool backyard… games room… everything you would want for a holiday getaway! Our thanks to Jess and Aaron! We would definitely return if in the St. Augustine area in the future!
Guest favorite

Home in St. Augustine

4.96 out of 5 average rating, 141 reviews

Large Beach House - 2 Full Kitchens, Hot Tub

JoanneRating, 5 stars1 month ago
Having the multiple bedrooms and bathrooms was great. Enjoyed the hot tub. Within walking distance for a stroll on the beach. Not far, only about 15 minutes to downtown St. Augustine. Owners response time was great. I would stay again.
Guest favorite

Home in St. Augustine

4.88 out of 5 average rating, 219 reviews

2BR Cottage -- Walking distance to Downtown St. Aug

LisaRating, 5 stars3 weeks ago
We had an amazing stay! The location is perfect—just a short, easy walk to all the downtown activities, restaurants, and shops. Glenn and Kelly were fantastic hosts, always quick to communicate and incredibly helpful throughout our stay. The house was spotless and had everything we needed to feel comfortable. We couldn’t have asked for a better experience and would highly recommend this place to anyone!
Guest favorite

Home in Palm Coast

5 out of 5 average rating, 10 reviews

Beachfront Escape with Pool & Spa | Built in 2024

JosephRating, 5 stars2 weeks ago
Our stay at Cinnamon Beach was great. This was a family escape. The unit was pristine and beautiful. The social area was roomy, comfortable, and clean. The kitchen was well stocked with all the necessary appliances and needs for cooking. Bedrooms were comfortable, stylish, and well appointed. The hot tub was a highlight as the weather was not as warm as we hoped it would be coming from the northeast. Finally, the elevator was a vital bonus for our daughter with a disability. David and his staff were also fantastic. They were proactive in making sure our needs were met and responsive to making the experience special. As an example, Andy, the house manager, adjusted our hot tub settings remotely and also went out of his way to find pickleball facility options for our group. The clubhouse and workout facilities were adequate but had limited hours which limited our use. The development is very safe with excellent security. Overall, a great experience.
Guest favorite

Home in St. Augustine

4.85 out of 5 average rating, 132 reviews

St. Augustine Beach House - Steps to Beach.

EthanRating, 5 stars5 months ago
We loved the house, it’s in a good location that’s close to everything we wanted to do & see. The kitchen was well stocked with cooking ware and utensils. I loved that we had a fridge upstairs and downstairs and that both floors have their own living area. In short it was better than we expected and we probably will stay here again in the future!
Guest favorite

Home in Saint Augustine

4.95 out of 5 average rating, 421 reviews

Walk to EVERyTHING Downtown within minutes.

CynthiaRating, 5 stars4 days ago
Fantastic location! We were able to walk most every place we wanted to visit. The house is located in a neighborhood experiencing positive change through renovations. There were three of us, & we felt safe walking after dark from St George St. The house has been remodeled & had everything we needed for our stay. There is even a small back deck area with outdoor table & chairs. Parking for our one vehicle was easy. Pictures in the listing are current and what we found upon arrival. The house was very clean. Blake was proactive with communication & made sure we knew he was available if needed. We would stay again if back in the area.

Private house rentals

Superhost

Home in St. Augustine

4.8 out of 5 average rating, 5 reviews

2 Houses 1 Property! Minutes to the beach!

KristineRating, 5 stars25 months ago
Absolutely perfect, exactly as described but better. Pictures do not do it justice. Will definitely go back! No issues with check in, clear instructions.
Guest favorite

Home in St. Augustine

4.88 out of 5 average rating, 128 reviews

The Beach House at Crescent Beach

TammyRating, 5 stars1 week ago
Great beach house! It was just 2 of us, but there was planety of room for a bigger group. Clean and comfortable. Being across from Cresent beach was fantastic. Would definitely stay again!!
Superhost

Home in Palm Coast

4.77 out of 5 average rating, 95 reviews

Cozy Palm Coast Home w/private heated pool

Courtney ERating, 5 stars2 weeks ago
The home was beautiful and clean. Great location. Palm Coast is a peaceful and beautiful community.
Guest favorite

Home in Palm Coast

4.94 out of 5 average rating, 126 reviews

Poolside Ocean Living for the Family

MelissaRating, 5 stars3 weeks ago
Great place! Within walking distance to the beach and had local restaurants close by. The house was fully stocked and very clean. We felt right at home and Erin was a very responsive and helpful host !
Guest favorite

Home in St. Augustine

4.86 out of 5 average rating, 7 reviews

Palms & Porches Paradise

KimmyRating, 5 stars2 months ago
We had a great stay. We absolutely fell in love with what the city had to offer. The home was cozy and clean. The home is about a 15 minute walk to the historic district which was nice being able to walk our entire stay. I would recommend this home to anyone visiting the area. We will absolutely be back.
Guest favorite

Home in St. Augustine

4.98 out of 5 average rating, 108 reviews

Country Cottage 3-bedroom home with free parking

KarinaRating, 5 stars1 week ago
We can definitely say we enjoyed our stay, thank you for everything you had available to us.
Superhost

Home in St. Augustine

4.75 out of 5 average rating, 118 reviews

Uptown "Hide-Out" Stylish Home in Prime Location

milesRating, 5 stars3 days ago
very responsive host. willing to do what is needed from guests and keeps a clean area
Guest favorite

Home in St. Augustine

4.97 out of 5 average rating, 36 reviews

Modern Magic at the Beach

RobynRating, 5 stars3 weeks ago
Such a lovely place in St Augustine - we have family in the area, and I don't plan on staying anywhere else ever again unless we have to!! The beds are comfy, as is the couch - and the living area is just fantastic. The neighborhood is lovely, too; trees and birds abound. We will be back!!

Destinations to explore