Holiday rentals with a pool in St. Augustine

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.

HtdPool w/Arcade, Fire, GolfCart Access, 1.2 mi DT

ISLE BE BACK 🌴— brand NEW modern home! **Golf Cart Access for an additional fee Please inquire if interested!** 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 ✔Self check-in & free parking

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!

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!

courtyardtreehouseinthehistoricdistrict

You have found your cozy oasis tucked in a (Real) Treehouse lodged in Ancient Oak. Set in a lush tropical garden in the historic district. It’s a minimalist’s dream, exemplifying the appeal of tiny living: compact, clean, efficient and 2 1/2 blocks to the historic districts shopping and restaurants. Relax on the Sun Deck, Rain Deck or in the Courtyard’s Tropical Garden The day time peaceful beauty is only eclipsed by the the nighttime display of laser lights projected onto the oaks canopy.

Downtown • Historic Whitney House • Luxury Baths!

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.

361 Fun in the Sun | Direct Oceanfront Ground Floor

Direct Oceanfront, ground floor flat unit, no stairs. Located in Crescent Beach at Summerhouse. Family oriented complex located on over 25 acres with four pools and large grass areas. Highly desired 2 bedroom unit. This property is ground level and directly oceanfront. Flat style layout not a townhouse, there are two steps to the front door but otherwise no stairs. Sliding door opens directly to covered back porch. Please see our our other property 461 More Fun in the Sun, 3 Bedroom

Heated Pool, Tiki Lounge, Steps to Beach, Games

Save my home by clicking the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* >Sparkling heated pool (pool heat - $60 day/$350 wk) >Steps from sand! (1 min walk) >NOW with a new Tiki Bar in garage! >Blocks to boat ramp, bring your boat + jet-ski! >Dogs OK! 2 dog max (w nightly fee) >Beach gear >Propane BBQ >DT St. Aug is a 10 min drive >Drip coffee pot >Washer + Dryer >2-3 parking spots >Cable in LR, other TV's are smart.  >3 days of supplies (TP, trash bags, pods, etc.)

Sunset Cove 2 - Pool - Sea Views - Walkable

Stunning new luxury 2br/2.5ba pool home with peeks of Salt Run and Anastasia State Park: * Pool Heat Available for $30 per day - Contact us after booking for details * Private pool + backyard * Parking for 3 cars * 2 king bedrooms w/ en-suite bathrooms & smart TVs w/ Netflix * 2 min drive (or 20 minute walk) to historic downtown St. Augustine * 2 min drive to the beach (Anastasia State Park) * 5 min walk to lighthouse, Alligator farm, restaurants & bars * Fully stocked and equipped kitchen

Perfect location 2 Bedroom Private Hot Tub

Couples Retreat Near Downtown St. Augustine. 0.5 miles from the Bridge of Lions. Enjoy a secluded courtyard, relaxing water fountain, and new 4-person hot tub. Wine down and watch the sunset in a peaceful setting after a exploring. Off-street parking is included. Restaurants, bars, coffee shops, and local favorites are only steps away. Perfect for a romantic getaway, weekend escape, or special occasion. Special requests and accommodations are available to help make your stay unforgettable.

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.