Vacation rentals with a pool in St. Augustine

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Top-rated rentals with a pool in St. Augustine

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Rental unit in St. Augustine

4.97 out of 5 average rating, 156 reviews

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 :)

Guest favorite

Condo in St. Augustine

4.86 out of 5 average rating, 347 reviews

Condo in St. Augustine’s World Golf Village Resort

Escape to St. Augustine and enjoy a one bedroom studio with new brand new renovations and upgrades! Located within the private gates of the World Golf Village in the Laterra resort, home of the King and Bear Golf Course. Explore the resort amenities including access to golf, multiple pools, a full service spa, lighted tennis courts, hot tub, and fitness center. Minutes away from restaurants, shopping and the Golf Hall of Fame. Travel to Historic St. Augustine and beaches in less than 30 minutes!

Guest favorite

Condo in St. Augustine

4.91 out of 5 average rating, 144 reviews

Anastasia Island 1 ~ Beach, Relax & Explore

Large one-bedroom condo with open space living, kitchen and dinning room full of natural light leading from the balcony. Bedroom has a large walk-in closet and a king bed with access to balcony. The condo comes complete with a full kitchen, washer and dryer, high-speed fibre internet, pots and pans and basic pantry items. This condo sleeps up to 4 people, best suited for 2 adults and 2 children. Queen air mattress with deep sheets and topper for optimum comfort, and a single mattress in closet.

Guest favorite

Home in Saint Augustine

4.99 out of 5 average rating, 384 reviews

Your Home Away From Home

1,800 SF, 2 bedrooms, 2 1/2 bathrooms, on a secluded 5 acre lot just minutes from Historic Downtown and St. Augustine Beach. The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms (1 with TWINKLE mattress) ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small upcharge for 5 or more. Motorcycle friendly! We also do live on the property!

Guest favorite

Condo in St. Augustine

4.98 out of 5 average rating, 119 reviews

Alice's Palace Alice in Wonderland St Augustine FL

Welcome to Alice's Palace; a sophisticated twist on Alice in Wonderland. This unique Madhatter tea party styled 1 bedroom private condominium is like no other. It has a large fully equipped kitchen, spectacular forest King bedroom, onsite spa, stunning pool and hot tub. Located in the King & Bear golf community of World Golf Village and boasts 2 World Class Golf Courses-King & Bear/Slammer & Squire and just minutes from Historic Downtown St Augustine, Outlet Shopping and many amazing beaches

Guest favorite

Condo in St. Augustine

4.96 out of 5 average rating, 104 reviews

Pelican Inlet 2 Bedroom Condo Steps from the Beach

Enjoy this newly renovated 2 bedroom 2 bath condo for your dream getaway. This is a ground floor unit in the "B" building which means you are just steps to the beautiful Crescent Beach, Matanzas Inlet, pool, tennis courts, pickleball, and more. Just bring your swimsuit. Condo includes beach towels, chairs, boogie and skim boards, beach toys, 2 kayaks, paddleboard, pickleball paddles and tennis racquets. You'll be just a short drive from historic St. Augustine with it's many attractions.

Guest favorite

Guesthouse in St. Augustine

4.95 out of 5 average rating, 324 reviews

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.

Guest favorite

Rental unit in Lincolnville

4.96 out of 5 average rating, 103 reviews

F2 Downtown, POOL, beaches, free parking!

Relax in the middle of Historic Lincolnville 10 minutes walk from Flagler College, the bay area, and the main attraction. Large heated pool (April 1 - November 1) and beautiful back yard shared by our 4 apartments. This downstairs historic apartment has all the modern conveniences with new appliances, TV's in living room and both bedrooms, wireless access and availability of Netflix, Hulu, Roku, CNN, FOX, E, Bravo, HGTV, TLC, and much more. Free parking on premise and free street parking.

Guest favorite

Guesthouse in St. Augustine

4.92 out of 5 average rating, 112 reviews

Heated Pool Side 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.

Guest favorite

Guest suite in St. Augustine

4.96 out of 5 average rating, 592 reviews

Sheepdog Hideway - on Anastasia Island near Amp!

Awesome, private guest suite located on Anastasia Island near the St Augustine Amphitheater! Walking distance to Anastasia State Park! Enjoy staying on the island without all the hustle of a hotel. We have beach cruiser bikes available for use! We are 1.5 miles from the closest public beach access and a 3 mile bike ride to downtown St Augustine! Update for COVID-19 pandemic: We will be spraying all hard surfaces with EPA-approved sanitizer to do our best to make sure surfaces are safe.

Guest favorite

Guest suite in St. Augustine

4.97 out of 5 average rating, 110 reviews

Bohemian Rhapsody King Suite St. Augustine at WGV

Welcome to Bohemian Rhapsody. This Artist inspired King Studio is like no other. Located in Laterra Spa World Golf Village. Enjoy the stunning onsite pool, hot tub and Circles of Wellness Spa. Golf at The Slammer & Squire and King & Bear Golf courses. Visit the World Golf Hall of Fame Museum, IMAX Theater and the King & Bear Clubhouse just minutes away. Historic downtown St Augustine, Anastasia Island, St Augustine Beach 20 mins away! Bonus...the St Augustine Outlets 10 minutes away!

Superhost

Condo in St. Augustine

4.85 out of 5 average rating, 262 reviews

Luxury 1 BR 1 Bath World Golf Village Penthouse

Welcome to St. Augustine!! Wonderfully located in the Laterra Condos this Luxury 1-bedroom, 1-bathroom vacation rental offers resort amenities you’ll love coming home to after exploring downtown’s Castillo de San Marcos, the Fountain of Youth or St. Augustine Beach! Located in the King and Bear Golf Course. Explore the resort amenities including access to world class golf courses, multiple pools, a full service spa, tennis courts, hot tub, and state of the art fitness center