Holiday houses in Jay

Large Mid-Century Home w/Bay View & Ancient Trees

Large nicely furnished 4/4 home located high on a hill overlooking Escambia Bay in Pensacola. This unique home features a large yard & relaxing views of the bay & towering trees, interesting artwork, 2 huge decks, 2 balconies, 70" big screen 4K TV, large open living & huge master suite. Great location short drive from beaches parks & trails. 10 mins from historical downtown, bars and restaurants. 10 mins to Pensacola Airport 25 mins to Pensacola Beach 28 mins to NAS 1 hour to Fort Walton/Destin.

Cloverdale Cottage (no cleaning fee)

Modern comfort with a cozy, welcoming feel. This rental features stylish interiors, a well-equipped kitchen, and a bright, relaxing atmosphere. Guests have access to a shared pool (with the neighboring property), perfect for unwinding after a day of exploring. The pool is open from Memorial Day to early October. While guests are welcome to visit, NO PARTIES OR EVENTS ARE PERMITTED. Important: The twin bed is located in a loft and is accessed by a ladder. It may not be suitable for all guests.

The Sunset Cottage

Come make memories you won’t forget in our beautiful, romantic tiny house. Watch the sunrise over the fields while sipping a cup of coffee. You will Enjoy exploring the nearby Coldwater Creek during the day, Or if you rather relax on the most beautiful beaches in Florida, it is a short drive. After a busy day, enjoy a magnificent view of the sunset or watch the deer as they approach the fields from the East. Please understand we are still improving the outdoors with additional landscaping.

the SighLo! Just N of Pensacola near I-10 & Hwy 29

Discover a true hidden gem- an authentic grain bin home with comfort, curves and unmatched character! Just minutes north of Pensacola with its sugar-white beaches, laid-back feel and rich history, you'll find the SighLo to be a fresh and unique accommodation for your beach vacation, staycation, local events, family time and more! Distance to beaches and other popular venues are listed below. * No children under age 13. 📸 Photography welcome! Ask us about one day bookings for a photo shoot.

The Pine House Pace, FL

Enjoy this UNIQUE retreat! Located on 3 acres of lush pines, this home is the perfect getaway for you or your family. With the romantic modern vibe of the house, you are sure to feel RELAXED, REJUVENATED and ready for whatever is next. Cool the day off in our backyard SITTING POOL, or read a book in our 7 ft SITTING WINDOW. Watch the pines sway through our living room observing windows or have friends over for dinner at our outdoor dining area! No matter the reason, the Pine House is for you!

W&W Airbnb

Kick back and relax in our studio Apt . Brewton is a small town with lots of charm. Jennings Park is close by and has a paved walking trail Plenty of restaurants ElReys Mexican, Happy kitchen Chinese. David’s Catfish, Camp 31 BBQ, simply donuts and so much more. There is a laundry mat conveniently located less than a mile. We are not responsible for water, Power or Internet service issues that may occur during your stay. THINGS TO NOTE: We do have a rooster that is fond of crowing. Lol

Quiet, Cozy Farmhouse

Take a load off in this peaceful farmhouse from a simpler time. Get back to nature in a home surrounded by dozens of acres of farmland and Conecuh National Forest. The house is located on a farm that has been active for 4 generations. If you're looking for activities, there's no shortage here! This property is conveniently located for those with an interest: hunting, fishing,walking trails, and just 70 miles from Florida beaches! Also, 15 miles from the ATV park, Boggs and Boulders.

Rustic and Elegant Log Cabin

Forget your worries in this spacious and serene space located in the Conecuh National Forest. Cabin has small amount of steps on front and is 3 levels on the back, overlooking the forest and trail down to the creek. Spacious back porch with several comfortable rocking chairs allows for birdwatching and visiting. Down the trail 2-3 min walking or driving is a covered pavilion and beautiful creekside private sandbar. Wifi and phone are spotty. Conveniently located close to fishing lakes.

Edna's Barn

Experience country charm in addition to convenient location- just 1.1 mile off interstate 10! Grocery stores and your favorite restaurants are also close by but you’ll get a good nights rest in this quiet neighborhood. It’s around 35 minutes drive to beaches depending on traffic. The barn was built in the eighties and housed chickens, rabbits and a cow but was repurposed as a dwelling in 2004. Completely modernized in 2022, you can enjoy a unique space with all the comforts of home!

From our garden house to yours

We think you'll like the recent renovations to our Garden Home... Convenience and comfort for your gulf coast getaway. Situated in a quiet neighborhood of Milton, FL, the Garden Home is located within 10 miles of the Milton Riverwalk and 45 minutes from Navarre beach. Whether you’re visiting for work, to explore the beaches/ bays, and/or to experience the charms of our beautiful Emerald Coast towns, we invite you to choose our Garden Home for your overnight accommodations!

Enjoy Low Fall and Winter Special Rates !

Tranquility awaits in this fully equipped penthouse with views from the 21st floor of the beautiful Gulf of Mexico. Island views as well. The master is equipped with a king bed and flat screen TV and jacuzzi tub in the bathroom. 2nd master suite has private bath and entry to balcony! Spacious open living areas allow everyone to be together. Kitchen is equipped with everything you need. Short walk to beach access. Next to the Lifestyle Center activities & amenities!

Waterfront with kayaks* Blackwater River Shanty

Enjoy nature in this 2 bedroom stilt house on Paradise Island surrounded by the Blackwater River- just a 30 minute drive to Gulf Beaches! Kayak around the island, enjoying the turtles & birdwatching, or boat or drive to downtown Milton to dock and dine at Blackwater Bistro or Boomerang Pizza. There is a boat ramp, boat house, 4 kayaks and life jackets for guest use. Easily visit Navarre Beach, vibrant Downtown Pensacola, Pensacola Beach, or Ponce de Leon Springs.