
Holiday rentals with a pool in St. Augustine
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in St. Augustine
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Traveler’s Nest of uptown St. Augustine with pool!
The Traveler's Nest is a unique and cozy studio apartment with a kitchenette, private backyard and access to a huge pool located in a quiet historic uptown St. Augustine neighborhood. It's just minutes to the Old City and Vilano Beach and Fort Mose National Park and Museum is 3min walk within the neighborhood! In addition, it's close to all your necessities (groceries, liquor store, restaurants, fast food....etc.) and there's a huge pool to relax and cool off when your not out seeing sites :)

Driftmark Cabin - RV friendly, Pool + Beach!
Experience the ultimate beachside getaway at our fully renovated Airbnb, just steps away from the sun-kissed sands. This luxurious retreat offers modern comfort with a private pool and inviting hot tub, allowing you to unwind in style. The recently upgraded interior boasts premium amenities, ensuring a relaxing stay. Outside, lush turf landscaping surrounds the pool, creating an oasis of comfort. Whether you're lounging by the pool, or enjoying the beach a stone's throw away, Driftmark delivers.

HGTV DesignerHome•HeatedPool•Walk/Bike 2 Downtown
Off Street Parking 3 Min Drive/ 15 Min Walk to Historic Downtown 2 Min Drive to the St Augustine Amphitheater 2 Min Drive to Anastasia State Park Beach 1 Min Drive to Anastasia Fitness Club/Suana-Steam Rm/Pool Looking to get away from the hustle & bustle of the city? This designer home with an amazing pool is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a minutes away. With spacious living & modern amenities, the Home offers maximum comfort

The Garden Casita in St. Augustine Florida
Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

2023 Lux Home 4bd/3.5ba+SaltPool+HotTub+Walk2Beach
* Built in 2023- luxe coastal furnishings & linens * Featured in 2024 Good Housekeeping Mag🌟 * 2 King Suites (1 on each floor) | 2 Queen Bedrooms | 3.5 Baths * Private Saltwater Pool & Spa/Hot Tub * Poolside Cabana | Outdoor Kitchen | Front Porch * Bikes, Beach Toys, Beach Chairs * Lush Tropical Landscaping * 0.2 miles - gorgeous quiet beach * 5.5 miles- historic downtown St Augustine- The oldest city in the United States! * 0.2 miles - Cap's Restaurant for sunset dinner on the water

Full Condo in St. Augustine’s World Golf Village
Escape to St. Augustine and enjoy a one bedroom condo with new brand new renovations and upgrades! Explore the resort amenities including free unlimited access to three pools, a hot tub, lighted tennis and pickleball courts, playground, and fitness center. Located within the private gates of the World Golf Village, home of the King and Bear Golf Course. Minutes away from restaurants, shopping and the Golf Hall of Fame. Travel to Historic St. Augustine and beaches in less than 30 minutes!

Heated Pool Beach Bungalow Steps to the Ocean
Beautiful brand new in 2022 en-suite Bungalow beach side! Perfect for a romantic get a way or just one person, just 600 steps to the beach. Five minutes to the St Augustine pier and 10 minutes to the oldest city in the US, Historic Downtown St Augustine. Not only do you have the most comfortable bed to fall into, a 50" TV, recliners and an amazing heated pool. Beautiful beach sunrises, fishing, hiking, Concerts at the Amphitheater. For your safety you have an electronic keyless entry.

Beach Condo, Pools, Bikes, Short Walk to Beach
Relax and unwind at our beautiful beach getaway. This one bedroom condo is located close to all St. Augustine has to offer. You can walk to the beach or take a quick drive to historic downtown. Ocean Village Club is a gated complex that has private beach access just a seven minute walk from your door, two swimming pools, tennis courts, grilling area, and free parking. This second floor unit is light and airy, immaculate, and beautifully decorated. We are family owned and operated.

Charming Rustic Boathouse
Come stay at our rustic boathouse along the serene river. Its weathered, wooden, exterior exudes charm, adorned with unique decor. The sunlight reflects the water, casting shimmering light against the boathouse. Surrounding it, is lush greenery and trees that create a picturesque backdrop. Inside, the boathouse is cozy and inviting, with simple furnishings and the gentle scent of wood. It's a haven where one can escape the bustle of everyday life and embrace the countryside.

Newly renovated! Steps to BEACH & POOL!
Our little slice of paradise is situated in the heart of St. Augustine Beach right on A1A Beach Blvd. Our unit, recently renovated, is just steps from the beach and closest building to the pool! 2 outdoor pools (1 heated in winter), 5 hot tubs & tennis courts. Perfect location to enjoy our beautiful beaches & all that Anastasia Island has to offer! Historic St. Augustine is less than 7 miles away. Unit is equipped with everything you need for a perfect beach vacation!

Pool home oasis steps to ocean
Cottage style home with comfortable porches to enjoy sound of ocean waves breaking on the front and back porches. Pool in the back yard (heated by request for $50 per day) cookshed, fenced with lush trees and woods to the east. The inside looks large with high wood ceilings and multiple windows and glass doors to the beautiful pool area. Located on a dead end street in a family neighborhood with 5 star restaurants nearby. Fifteen minute drive to downtown St. Augustine.

Bel oc'ean, St Augustine beach
Close to shopping and restaurants. 15 min drive to historic downtown. Perfect for families, couples, friends, or solo travelers. Enjoy having no stairs to climb! Family friendly vacation. New king bed. Fully equipped kitchen, free WiFi, 2 pools (one heated), full size washer/dryer in unit, Smart TV, pet friendly 1 Dog Only, requires $50 (cash) registration fee upon check in. There is also a flat $15 Pet Fee for guests bringing a dog. **Strictly NON-SMOKING unit**
Popular amenities for St. Augustine rentals with a pool
House rentals with a pool

Heated Pool/Hot Tub 1 mile to dwntn/beach

Your Home Away From Home

Tide Pool - Heated Pool/Hot Tub/Golf Cart

Lakeside Retreat |Private Pool| 8min walk Downtown

Oasis Pool House! Close to DT, Beach & Boat ramp

Peaceful Oasis Pet Friendly heated Pool & Gameroom

Walk 2 Beach | Game Room | Firepit |Heat/Salt Pool

Spacious St. Augustine Home "The Gold Knocker"
Apartment rentals with a pool

Ocean Side Complex w/ Heated Pool B-15

Sand & Surf! Nights of Light Deals-Oceanfront Pool

Direct Oceanfront ~ Fantastic Views!

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool

F1, Downtown, POOL, beaches, porch, parking!

Summerhouse - Direct Oceanfront Corner Unit

Seagrass Condo - ocean front, 1 bedroom/1bath

Family Beach Condo - Steps To The Sand Or Pool
Other holiday rentals with a pool

Luxury Home with Pool, Pickle Ball and Hot Tub

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

Palma Beach House

Fun Waterfront Retreat, Heated Pool, Rooftop Deck

Luxury Costal Oasis Close to Beach & Amphitheater

St. Augustine Palm & Spa Retreat 3 pools and Golf!

Luxury Resort Style w/ Pool & Gym close to Beach

Spacious home w/ pool & gym
When is the best time to visit St. Augustine?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $283 SGD | $290 SGD | $323 SGD | $309 SGD | $304 SGD | $337 SGD | $341 SGD | $298 SGD | $281 SGD | $268 SGD | $296 SGD | $312 SGD |
| Avg. temp | 13°C | 15°C | 17°C | 20°C | 24°C | 27°C | 28°C | 28°C | 26°C | 22°C | 17°C | 14°C |
Quick stats about holiday rentals with a pool in St. Augustine

Total holiday rentals
Explore 480 holiday rentals in St. Augustine

Nightly prices starting at
St. Augustine holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 27,780 verified reviews to help you choose

Family-friendly holiday rentals
420 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 190 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
480 of St. Augustine holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across St. Augustine rentals

4.9 Average rating
St. Augustine stays are highly rated by guests – averaging 4.9 out of 5!

Nearby attractions
St. Augustine’s top spots include Lightner Museum, St. Augustine Alligator Farm Zoological Park and St. Augustine Distillery
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- Ponte Vedra Beach
- TIAA Bank Field
- Old A1A Beach
- Summer Haven st. Augustine FL
- San Sebastian Winery
- Daytona Beach Boardwalk and Pier
- Vilano Beach
- Daytona Lagoon
- Lightner Museum
- Fountain of Youth Archaeological Park
- Boneyard Beach
- Kathryn Abbey Hanna Park
- Crescent Beach
- Butler Beach
- Matanzas Beach
- Pablo Creek Club
- Eagle Landing Golf Club
- Ravine Gardens State Park
- Worlds Most Famous Beach Daytona Beach
- MalaCompra Park
- St. Augustine Alligator Farm Zoological Park
- Adventure Landing Jacksonville Beach
- Neptune Approach
- Amelia Island State Park
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