
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
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Historic District, St. Augustine rentals with a pool
House rentals with a pool

Heated pool retreat! Walk to historic downtown
The house was perfect for my group of 6 adults. The house perfectly clean. The pool was amazing to hangout at and cool off. Will definitely use again in the future.

Fun & airy Florida vacation home with private pool
Our stay at this Airbnb was absolutely wonderful! The home was spotless, beautifully decorated, and had every amenity we could possibly need. The beds were incredibly comfortable, the kitchen was fully stocked, and we loved relaxing in the cozy living room after a day of exploring. The location was ideal, close to great restaurants, shops, and attractions, but tucked away enough to feel peaceful and private.. We felt completely at home and are already planning our next trip back. Highly recommend this Airbnb to anyone looking for a clean, comfortable, and memorable place to stay!

Sunset Cove - Heated Pool - Sea Views - Walkable
Extremely beautiful modern home! Loved the layout of the house! The pool was the cherry on top! Just a quick 5 minute drive to either downtown with tons of shops/restaurants or 5 mins to the beach! Will definitely be back!

Walk downtown, pool beach min to everything pet ok
We had a wonderful family reunion at Theresa’s lovely house. There was something for every age group to do. The yard was very private and yet you could walk to coffee shops and even to downtown. The pool was wonderful and the house was spacious. The host was very accommodating and even my dog felt welcomed! Would definitely recommend and plan on staying again.

Spacious St. Augustine Home "The Gold Knocker"
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

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.

Peacock Cottage - New Construction/Heated Pool
We had a wonderful time enjoying the pool and having a home base to explore the historical district of St. Augustine. Would 100% recommend especially if you are traveling with young kids

17 Palms Beach House
We had a fantastic time at 17 Palms Beach House. The house was even better than the pictures showed. It was clean and comfortable with a kitchen that had everything needed for our stay. The beds were comfortable and the linens ultra soft. Even the pillows were perfect. The pool was a big hit with everyone with all the toys and beach towels one could wish for. The beach was an easy walk right down the road. We had a couple of questions and Lyndsey answered quickly and was so nice. I highly recommend staying here, you won't be disappointed.
Condo 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.

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 .

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool
We very much enjoyed our stay! The condo was amazing. The pools were very clean and peaceful. Our host was very responsive and kind. The walk to the beach wasn’t that bad at all! I loved the security features and felt safe with my daughters. I would recommend this condo to friends, and would stay here again.

The Salty Suite Resort style condo
This Airbnb was perfect for a stay for two people. The space was clean, spacious, and had everything we needed. The location was quiet yet close to restaurants and the beach! We’d definitely stay here again!

~Hot Tub~Just Steps to the Beach~King Bed~2 Pools
It’s a nice cozy place within walkable distance to the beach. We had a great stay! I would definitely recommend this place.

Bring the boat! 2 Bedroom Steps from the Beach
Best rental my family has ever gotten. Walked to the beach and great food selections. Had toys for the kids and multiple items for the beach for use.

St Augustine Beach 2 Bed Condo
Super location, a stones throw to any food you could think of! There were bikes available for use which is always nice in St. Auggie, will be back!

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!
Quick stats about holiday rentals with a pool in Historic District, St. Augustine
Total rentals
30 properties
Nightly prices starting at
$167 NZD 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
- Guana Reserve Middle Beach
- North Beach Guana River Preserve
- Lightner Museum
- Palm Harbor Golf Club
- St. Augustine Alligator Farm Zoological Park
- Matanzas Beach
- MalaCompra Park
- Eagle Landing Golf Club
- Bent Creek Golf Course
- Driftwood Beach
- Jungle Hut Park
- Ravine Gardens State Park