Holiday rentals with a pool in St. Augustine Beach

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.

Pink Palms *Pool* Party ~ Walk to Downtown

🏝️ Luxurious Private Heated Pool Home In Historic Downtown and Family Friendly! - Private Heated Pool & large backyard with tons of gorgeous palms - Outdoor cabana with grill, fans, pool table, kid toys, bocce, corn hole, recessed lights and seating - Walking distance to the Castillo de San Marcos Fort, Fountain of Youth, Uptown shops, The Bayfront and St. George Street - Less than 10 mins to Vilano Beach 🌊 - Sleeps 6/ 2 King beds, 2 XL twin beds (daybed trundle) - Pet Friendly - Event Venue

Historic Designer Home • Luxury Baths • Steps2DWTN

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

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 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

Quiet, Updated Condo - Pool, Bikes & Pickleball!

Relax at our beautifully updated 2BR/2.5BA condo in a quiet, family-friendly St. Augustine Beach community! Newly renovated guest and powder bathrooms completed for summer 2026 (not yet pictured). Enjoy easy beach access via a private boardwalk, pool, hot tub, tennis & pickleball courts, beach gear, bicycles, private balconies, and a fully stocked kitchen. Conveniently located near restaurants, shops, and historic downtown St. Augustine—perfect for your next coastal getaway!

Beachy Condo| Steps to Beach | Pools | Hot Tubs

Champagne Sunrise on Private Balcony Anyone? Unwind at our updated St. A​ugustine beach condo-just 150 steps to white sand beach. Dip into 1 of 5 hot tubs, cool off in 2 sparkling pools (one is heated for those cool winter days). Challenge friends to a tennis match, pickleball rally, or bocce ball showdown. Craving nightlife, history, and culinary delights? Walk to restaurants or take a trolley in historic Old Town St. A​. Full kitchen/laundry in unit. Private beach access.

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!

Oceanfront Retreat!

Welcome to our Oceanfront Retreat! Close to everything St. Augustine has to offer. Beautiful beach, outstanding restaurants, museums, magnificent architecture, and a strong history dating back to 1565. Everyone wants to feel relaxed and refreshed on vacation. We have created a space that is comfortable and inviting to accomplish just that. Equipped with new finishes to anticipate your needs for a luxurious vacation. We hope you enjoy our little piece of paradise!

Ocean Front Gem: Top Floor Corner Unit

Top floor, direct ocean front, 2 bedroom, 2 bathroom corner end unit condo with elevator and unobstructed beach views from both bedrooms, living room, dining room, kitchen and private balcony in beautiful St Augustine Ocean and Racquet Resort. We also offer the condo immediately next door for rent, Ocean Front Escape: https://www.airbnb.com/h/saint-augustine-oceanfrontescape. Our checkin process is contact free. We use a Nest lock on the front door.