Holiday houses in Elkton

Winter Hawk Hideout

15 minutes from ol' St Augui. Located in the heart of this typical Florida woods and nested by oaks that saw the Seminole War as we are walking distance from Ft Peyton and 2 miles away from where Osceola was captured. The house sits on half acre of gardens and the decor is ranch, asian and whimsical .The goal is for you to feel transported away for a while. I do have 2 very small, well behaved and quiet dogs and one never seen cat. They do not have access to your quarters or are allowed in.

Tiny House in the Woods

Escape to our charming tiny house tucked away in a tranquil forest, just 15 minutes from sandy beaches and only 20 minutes from Historic St. Augustine. With a scenic bike trail just steps away, this cozy Tiny House is the ideal base for surfing, cycling, or simply unplugging. Thoughtfully designed for comfort and simplicity, it features two inviting lofts, a well-equipped compact kitchen, and a private bathroom. Outside, enjoy your morning coffee beneath the trees or wind down by the fire pit.

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!

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

Zen Oasis | Heated Pool | Hot Tub | Beach 12-Min

Escape to our Zen Spa Retreat! Enjoy the soothing heated pool and hot tub, unwind on the expansive patio, or find tranquility in the zen-inspired interiors. This spacious 3 bedroom 2 bathroom is located in a quiet neighborhood close to Old St. Augustine, beaches and restaurants. Blackout curtains and smart TVs in every bedroom! Our fully equipped kitchen, washer, dryer, dishwasher, workspace and garage ensure convenience during your stay. Unwind in our serene oasis for the perfect Zen getaway!

Cottage on Animal Farm with Pool near St Aug

Experience your dream getaway on the farm! Our modern country cottage overlooks pasture with free ranging animals spanning across 11 beautiful acres including donkeys, peacocks, chickens, turkeys and more. Lounge by the pool, take in the breath taking evening skies, and relax with view of animals far off in the background. Hang by the fire pit, take a walk to visit the goats, donkeys, emus, alpacas, or go for a stroll down the beautiful oak lined roads nearby. The views & serenity are stellar.

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fully fenced backyard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant, LaNuvelle, trolley stop * 10 minute walk to central downtown

St. Aug cottage, great location!

Newly updated tropical cottage close to everything in St. Augustine and steps from the Matanzas River boat ramp. This 2 bedroom, 2 bath home has wood and tile floors and a lovely screened patio to relax looking at nature and listening to the bubbling fountain. Back yard is fully fenced. 3 miles to downtown, beaches, alligator farm, or the amphitheater. Beautiful area for walking along the Matanzas river and your well loved and cared for pets are always welcome. Boat parking available.

Cozy Studio 15 mins to Beaches & Historic Downtown

Outstanding location & amenities, 15 minutes to beaches, St. Augustine Amphitheater and historic downtown in a quiet, friendly neighborhood. Minutes walk to the intercostal, w/ piers & boat ramps, gorgeous views, perfect for walks. Close to lots of shopping & dining. Ample parking-trailers & boats welcome. Kid friendly w/ toys, pack & play + more. Laundry, walk-in shower, private entrance. Private deck w/ cheerful seating. Well equipped kitchenette. Easy drive to theme parks, Daytona + more.

St Augustine Entire Home, King Bed, Pet Friendly

Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!

Cottage w/pool on horse property, St. Augustine.

This 860 sf. cottage has all you need for a comfortable, private stay while visiting St. Augustine. Victoria Place sits on a 13-acre equestrian property, Enchanted Horse Acres, a magical place for nature lovers. Beautiful and quiet country setting only 20 minutes from the hustle and bustle of historic St. Augustine and the white sands of Crescent Beach. This is an ideal location between Orlando and Jacksonville with easy access to the freeway, only 45 minutes to Daytona Beach.

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.