
Holiday rentals with a pool in Historic District, St. Augustine
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Top-rated rentals with a pool in Historic District, St. Augustine
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Popular amenities for Historic District, St. Augustine rentals with a pool
House rentals with a pool

Pool/Hot Tub Home 1 mile to downtown/beach
St Augustine Family Trip #3 in the books. We have stayed here 3 years in a row and will be back next year. Heather has always been a great host. We always enjoy our time here. See you in 2026 Heather !!

1 Block to Beach! Heated Pool, Near Historic Dist.
We had a wonderful stay at this beach house just a block from the ocean! The location is unbeatable—so close to the beach, yet quiet and relaxing. The private pool was a huge hit with our group, and the home offered tons of amenities that made our trip comfortable and fun. The house was spacious and well-equipped, perfect for a family getaway or a group trip. We especially appreciated the little extras that made it feel like home. That said, there were a couple of small misses that are worth noting. The flooring could have been cleaner—it left our feet quite dirty after walking barefoot, which was surprising for such a nice property. Also, we would have appreciated having enough bedding for all the beds, as we had to improvise a bit. Overall, we had a great time and would absolutely return with just a few improvements. The location, pool, and amenities definitely outweigh the minor issues!

Your Home Away From Home
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! 😊

Canopy Oaks
I don't even know where to start... Rick's place was the PERFECT spot to celebrate my 40th with my girlfriends. The house was better than the pictures, the location was amazing and Rick was an amazing host! There was an issue with the AC the second day we were there and he had someone to the house to fix it same day! i can't wait to book this house again and enjoy another week exploring St. Augustine.

Walk 2 beach! Relaxing 3/2 Huge heated pool dog ok
our stay here was amazing! the place was clean and host was very nice and communicated regularly. it is just a short walk to a beautiful beach too. pool was nice, hot and clean. lots of little extra things like spices, ziplock bags, dish soap, and body care. the location couldn't have been more perfect for what we had wanted. thanks for a great stay!!

New LUX 4bed Saltwater, HEATED POOL, 2 Masters
Maya was EXTREMELY responsive, answered all my questions within minutes of sending her a message. The place was incredibly clean and beautifully decorated. The outside space was perfect for a family gathering. The pool and ability to dine outdoors and grill out (on a nice clean Weber Grill) was a highlight. The place accomodated our group of 8 perfectly. The living space provided a nice space for game night and eating our meals together. I would highly recommend this place. It was a quick easy walk to a very quiet, pretty beach. We will stay here again.

Splash & Explore
This Airbnb had the best layout, space, and number of beds and baths for our large family group that we've encountered in many years of gathering. It was also spotless and a fantastic location for everything we wanted to do in St Augustine. The host was very communicative, especially when I asked questions; response time was quick. There was only one small surprise that led me to give 4 stars instead of 5 for a couple of areas: description and value. The surprise was the pool is small, what I have heard referred to as a"cocktail pool" . We still had fun in it but with such a large group (8 adults and 4 kids), it was smaller than we hoped for. This was close to meeting the "value" category but I felt a little overpriced to not either be on water or have a large pool. Having said that, I would stay again, particularly in winter when the pool isn't as much of a factor.

HEATED, SALT POOL*Nearby Beach*GAME ROOM*Grill!!
Stay was very relaxing easy access to the beach close proximity to all amenities! would recommend.
Apartment rentals with a pool

Spanish Colonial Design One Bedroom Condominium
Nicki’s place was a perfect, peaceful and private getaway for my husband and I. We thoroughly enjoyed our stay! Close to a Publix and quick bites. Only a 25 minute drive to historic St. Augustine, and 35 minutes to the beach. We felt safe in the gated community and enjoyed the pool/hot tub.

++Perfect Romantic Getaway - Walk to the Sea
Ashley's place was a pleasure to stay. Everything you need was available. Beautiful beach and close to several great restaurants.

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool
We enjoyed our stay in Saint Augustine Beach at Todd's listing. The best part of the rental is the beach access which is about a 10 minute walk from the unit or you can park closer in visitor spots to get to the beach and beach pool even sooner. The place was clean, AC was great, and the shower was nice and warm. We would definitely stay here again if in the area! Todd was very responsive and friendly.

Ocean Front Gem; Top Floor Corner Unit
Wonderful time with family and friends for a much needed get away. We could not figure out the TV and Alan sent his friend and wife over to help fix the tvs. The friend and wife provided amazing food recommendations and places to go in downtown . Definitely recommend and will stay again .

Steps to Beach, Bikes & Beach Equipment Included!
Prefect beach condo! Had everything we needed to enjoy the beach for a couple days. Hosts were lovely and wonderful communicators.

4Ocean Front Condo With Pool unit 4
Really enjoyed our stay in Todd’s place he was a great host, with great communication. The condo had everything you would need on your beach getaway. Easy walk to the ocean. Beach was very clean and in a great location. I rate condo, host and beach a 10!!! Can’t wait to go back to St. Augustine beach.

The Flirty Flamingo St Augustine Beach 3 BR Condo
Cindy is rated super host. It's no wonder; she's easily accessible, responsive and delightful. The unit itself? 5 out of 5. Beautifully decorated and appointed. Great proximity to pools AND beach. My sisters and I enjoyed everything needed for a week-long stress free/care free vacation. We so enjoyed meals out on the balcony overlooking the lagoon pool. Would we go back? YYYEEESSS ... in a heartbeat. Thank you, Cindy!

Beach Condo, Pools, Bikes, 7 min walk to beach!
Very cute clean, used the bikes…came in for a perfect beach ride or community ride. I absolutely would like to go back and recommend a stay.
Quick stats about holiday rentals with a pool in Historic District, St. Augustine
Total rentals
30 properties
Nightly prices starting at
₹8,657 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Ponte Vedra Beach
- Summer Haven st. Augustine FL
- TIAA Bank Field
- Old A1A Beach
- Boneyard Beach
- Daytona Lagoon
- Daytona Beach Boardwalk and Pier
- Kathryn Abbey Hanna Park
- Amelia Island State Park
- Butler Beach
- Crescent Beach
- Fountain of Youth Archaeological Park
- North Beach Guana River Preserve
- Guana Reserve Middle Beach
- Lightner Museum
- Palm Harbor Golf Club
- St. Augustine Alligator Farm Zoological Park
- MalaCompra Park
- Matanzas Beach
- Eagle Landing Golf Club
- Bent Creek Golf Course
- Driftwood Beach
- Jungle Hut Park
- Neptune Approach