Vacation rentals with a pool in Anastasia Island

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Popular amenities for Anastasia Island rentals with a pool

House rentals with a pool

Top guest favorite
Home in St. Augustine
4.99 out of 5 average rating, 409 reviews

Your Home Away From Home

ShannonRating, 5 stars1 week ago
Fred & Linda’s place felt like we were right home. The place was very serene and tranquil right in the middle of St. Augustine. Anything we needed, it was there. The hosts also let us know that if we needed anything, to let them know. Their salt water pool felt great on hot afternoons and evenings. The kids loved the place. Even their little dog Ellie came to play ball with the kids. Would recommend staying here.
Superhost
Home in Palm Coast
4.88 out of 5 average rating, 123 reviews

Heated pool home w/boat dock, water front & Marina

RonnyRating, 5 stars2 weeks ago
Great place and wonderful host! Loved the layout of the home! 4 different accesses to the patio and pool area! We wish the waterfall for the pool had been working to drown out the sounds and conversations from neighbors lanais and some of the lighting was out but it was still enjoyable for our group! We would definitely book again!
Top guest favorite
Home in St. Augustine
5 out of 5 average rating, 128 reviews

Private oasis, private pool, exceeds expectations

DonnaRating, 5 stars2 weeks 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, 114 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

MonteneRating, 5 stars5 days ago
What a hidden treasure! I was looking for a getaway and what I found was a Haven. It surpassed all of my expectations. So peaceful, clean, and convenient. Close to everything yet tucked away into a quiet corner. Michelle is professional yet so friendly and helpful. Any questions you may have, she has the answer. Definitely one of my favorite places that I have ever stayed in the continental US. Five stars and two thumbs up!
Top guest favorite
Home in St. Augustine
4.98 out of 5 average rating, 157 reviews

"Once Upon A Tide" Beach House *Heated Pool* King

DanielRating, 5 stars1 week ago
Our family of 4 and my mom stayed here while visiting family for a wedding reception over the Memorial Day holiday weekend. Denise went out of her way to provide some very thoughtful welcome gifts for our family! She was super fast and responsive to any questions we had before or during our trip. We were blown away walking into Once Upon a Tide for the first time and seeing how beautiful it was! It truly felt like you were staying in a luxury beach house! Everything was clean, well-decorated, organized, and well-labeled to prevent any confusion about where things were or how to operate them. Our boys loved having night swims in the pool with the LED lights on, and we also enjoyed that the beach was just a few blocks away and easily accessible by golf cart. We enjoyed every minute of our stay at Once Upon a Tide, and we were so sad to leave!
Top guest favorite
Home in St. Augustine
4.99 out of 5 average rating, 100 reviews

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

LaurenRating, 5 stars5 days ago
Highly recommend! Whitney and John were great hosts and easy to work with. They were very responsive and accommodating. Home was absolutely beautiful! It was very clean and had everything our family needed! The pool was amazing our kids didn’t want to leave! Also easy beach access for kids. I can’t say enough good things about our stay! Will definitely be back!!!!
Guest favorite
Home in St. Augustine
4.84 out of 5 average rating, 228 reviews

Spacious St. Augustine Home "The Gold Knocker"

TristinRating, 5 stars6 days ago
Nicky was very responsive we were arriving early texted her and let her know she said it was ok if we went ahead and got to the house earlier than check in very helpfull she has a very pretty house a nice screened in pool and alot of good recommendations in a note book right in the house very well done we would definitely stay again
Top guest favorite
Home in St. Augustine
4.99 out of 5 average rating, 200 reviews

TopRatings•HistoricDowntownCharm•WalkTrolleyAccess

AnaRating, 5 stars5 days ago
From the moment we walked up to the home, felt like a home I would love to to live in. The house was beautifully decorated and had such a cozy feeling from the start. Loved how close it was to downtown St. Augustine.

Condo rentals with a pool

Guest favorite
Condo in St. Augustine
4.86 out of 5 average rating, 167 reviews

Escape to Paradise at Hibiscus Condo!

MaryRating, 5 stars2 months ago
Heidi's was one of two condos next to one another that we rented for a family week. Beautiful, clean, and incredibly well equipped. Kitchen had everything you might need, and a closet was stacked with beach toys and equipment. Pack 'n play available. We've been going to Hibiscus for 30-plus years, and this is one of the best units we've stayed in. Pool and hot tub right outside; short walk to the beach.
Guest favorite
Condo in St. Augustine
4.94 out of 5 average rating, 108 reviews

++Perfect Romantic Getaway - Walk to the Sea

KennyRating, 5 stars1 month ago
This place was very nice,close to the beach and restaurants. Ashley was very responsive and directions to get in the place were great. Definitely recommend this place to people!
Top guest favorite
Condo in St. Augustine
5 out of 5 average rating, 72 reviews

"Drift Away" at The Ocean Gallery

JordanRating, 5 stars1 week ago
Jonathan’s place was fantastic. Clean comfy and spacious. The spot was located next to the community pool and just a short walk to the beach access. The unit had everything for hanging out and cooking in the unit to beach accessories so we didn’t have to lug our own to his place. Would highly recommend and will be booking again!
Top guest favorite
Condo in St. Augustine
4.98 out of 5 average rating, 113 reviews

361 Fun in the Sun | Direct Oceanfront Ground Floor

ChristineRating, 5 stars3 weeks ago
I wanted to stay on a beach that was more secluded and private. We went into St Augustine many days, but I relaxed on the beach daily. Many days, I felt I had the beach to myself. It was amazing! The beach is beautiful, clean, and wide. The sand is white and sometimes pink. You can hear the waves in the condo. This is the closest we have ever been to the beach for a vacation. I was so relaxing. Prompt responses from Luke and Joslyn. My husband left his shirts in the closet and Joslyn offered to send them to use, which was very nice. This was a fantastic experience. We did go May 1-10, which is a good time to go before the crowds. We do recommend to go to St Augustine (downtown) during the week (less busy) and more beach time on the weekends.
Superhost
Condo in St. Augustine
4.73 out of 5 average rating, 194 reviews

Long time no Sea?-Oceanfront!-Summer Deals Now!

DorneRating, 5 stars1 month ago
Love staying at Chris’s places! This was our second stay, happened to be in a different unit. We will definitely try to go again! The view is awesome and the accommodations are perfect for us, simple and as described. Chris is a great communicator, very helpful and friendly.
Top guest favorite
Condo in St. Augustine
4.98 out of 5 average rating, 91 reviews

Family Beach Condo - Steps To The Sand Or Pool

DanyelleRating, 5 stars6 days ago
BOOK IT! Every single detail was as described. Brendan and Jessica have thought of everything ( including the stuff you forgot to pack). The view was amazing, the decor perfect, the coffee bar was awesome, beach accessories were so appreciated (we even added ours to the collection). I cannot say a single negative thing about our stay. I would most definitely rebook.
Top guest favorite
Condo in St. Augustine
5 out of 5 average rating, 90 reviews

Boutique Beachside condo with easy access to beach

EllenRating, 5 stars1 month ago
Skippers Hideaway was just so relaxing. This condo has everything you need to just kick back and relax. From a very well stocked kitchen to the comfortable, clean living room furniture and clean new sheets and towels in the primary bedroom & bathrooms. New front load washer and dryer, newer appliances in the kitchen. New laminate flooring through out. We will definitely be back!
Top guest favorite
Condo in St. Augustine
4.99 out of 5 average rating, 149 reviews

Alice's Palace Alice in Wonderland St Augustine FL

MystiRating, 5 stars1 week ago
Alice’s Paradise was magical! We loved our stay and Linda has done such a wonderful job! Every little detail was perfect!

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