Holiday rentals with a pool in St. Augustine

Brand NEW Beach House with HEATED pool!

Brand NEW vacation rental in St. Augustine! Gorgeous open floor plan that was designed and built specifically as a vacation rental. This home features 3 bedrooms, 2 full baths, huge 16ft ceilings and an amazing in-ground, heated pool! Enjoy your morning coffee on the front porch with natural privacy from the beautiful oak trees or lounge by the pool and entertain on the patio. 3 blocks from the beach, a block away from the intercoastal and a quick 10 min drive to historic downtown St. Augustine!

Downtown Luxury • Gourmet Kitchen • STEPS 2 DTWN !

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

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.

Charming Vintage Intracoastal Apartment

This breathtaking property is located on a quiet neighborhood street in Vilano Beach area on the river, minutes from the beach and a few miles from Historic Downtown St. Augustine. Apartment is on the second floor facing picturesque streets of Vilano Beach area. Waterfront private outside dining area with a grill, dock, and boardwalk are available on the waterfront side of the property. Famous local restaurants Cap's on the Water and Aunt Kate's are within walking distance from the property.

Htd Pool/Arcade, FirePit& PuttingGreen 1.2 mi DT

ISLE BE BACK 🌴— a brand NEW modern home! Dates fill quickly for spring & summer — save your stay now! Welcome to your ultimate St. Augustine getaway! Just 5 mins from downtown, this fun-filled retreat is perfect for families, friends, or anyone looking to relax and play. Swim in the pool, compete on the putting green, roast s'mores by the fire pit, or challenge your crew on the retro Pac-Man machine—all without leaving the house! ✔ Sleeps 8 comfortably ✔ Easy self check-in & free parking

Perfect Waterfront Retreat w/Pool & Rooftop Deck

You've found your waterfront oasis tucked under the White Birds of Paradise! This spacious retreat was formerly a commercial art gallery. Two queen beds, one full bathroom & full kitchen make for comfortable living! You have a fenced path leading you down to the beautiful waters of Salt Run where a rooftop deck & salt water in-ground pool invites you to relax and slow down. Less than a mile to downtown St. Augustine, a little over a mile to the Amphitheater and about 3 miles to the beach.

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

Coastal Sol|Heated Pool|6-min to BCH|Golf Cart

New Floridian-style beach home located only 6-min walk to quiet, secluded Vilano Beach access. Two-story, 3 bedroom, 2.5 bathroom layout with private, fully-fenced backyard with custom heated pool. Located in the Vilano neighborhood, our home is perfect for Florida beach vacations. Enjoy grilling out in the backyard, lounging around the pool or beach all day! 12-min drive into Historical Downtown St. Augustine. Beach supplies provided to guests - Pet-friendly property. GOLF CART available.

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!

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.

Historic St. Augustine 2/2 Duplex & Pool

About this space: Welcome to this 2 unit home located in Historic St. Augustine. This home is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This home has 2 bedrooms and 2 full bathrooms, a living room, kitchen, den and direct pool access. This space: This home is a 2 unit house Guest access: There is a lockbox on the door with a key inside Other things to note: Please keep in mind that the pool is a shared space :)

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.