Vacation rentals in Jay

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Top-rated vacation rentals in Jay

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Top guest favorite
A charming tiny house features a blue exterior and white columns supporting the porch. A welcoming yellow door invites guests, while the surrounding area is landscaped with mulch and small plants. Two chairs are positioned on the porch, offering a spot to relax.
Tiny home in Milton
4.98 out of 5 average rating, 111 reviews

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.

Top guest favorite
A modern retreat is showcased with a striking dark exterior and large glass windows. The wooden deck is complemented by outdoor seating, while lush greenery surrounds the home, creating a serene setting within the pine forest.
Home in Pace
4.94 out of 5 average rating, 212 reviews

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!

Guest favorite
An open kitchen area features modern appliances, including a stove and refrigerator. A small round table with two stools occupies the center, while natural light filters through a window adorned with a fabric treatment. Light-colored walls and wood-like flooring create a clean and functional space.
Apartment in East Brewton
4.94 out of 5 average rating, 88 reviews

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

Top guest favorite
The spacious living area features a large sectional sofa with light-colored cushions, complemented by a round coffee table. A sleek entertainment unit stands against the wall, with a flat-screen TV above. Natural light fills the room through large windows, enhancing the open layout.
Home in Milton
5 out of 5 average rating, 14 reviews

Family Time & Tides

Escape to Family Time & Tides, where we've poured our hearts into creating a welcoming space perfect for your family's relaxation and beach adventures. You'll find everything you need, from a fully equipped kitchen to cozy living areas designed for making memories together. Being just moments from the interstate, we have quick and easy access to the Gulf Coasts stunning white-sand beaches. Spend your time simply chilling your days away, soaking up the sun, and swimming in the emerald waters.

Top guest favorite
A welcoming exterior of a cottage is highlighted by warm string lights overhead. A paved pathway leads to the front door, surrounded by greenery. The carport provides sheltered parking space, with a gravel driveway extending into the serene natural setting.
Home in Walnut Hill
5 out of 5 average rating, 76 reviews

The Cottage at Steve’s Farm

The Cottage has everything you need to make your stay relaxing and comfortable. Take a stroll down a country lane, around the ponds. Watch the farm activities, or just relax under a tree and watch the sun go down on Steve's Farm and Market in peaceful Walnut Hill! This family friendly spot is sure to please your entire crew! Step out the back door and across the yard to Steve's country market for many food and snack items and local craft and gift ideas. The kids can fish, and mom can shop!

Guest favorite
An open living space features a comfortable sofa, complemented by a cozy throw blanket and cushions. Large windows allow natural light to fill the room, which includes a kitchen area with modern appliances. A soft area rug anchors the space, creating a welcoming ambiance.
Home in Milton
4.97 out of 5 average rating, 119 reviews

Blackwater Bay Mae's Cottage

Mae's Cottage is a peaceful little bay house located right off of Interstate 10 in Milton (< 1 mile) and is within steps to the beautiful Blackwater River and Bay. It is approximately 100 yards from water access where you can enjoy fishing, boating, kayaking or just watching the sun set. There is a public boat launch so bring your boat/jet skis/kayaks and fishing gear and head out to the beautiful waters of Blackwater Bay. Relax with the whole family at this peaceful little bungalow.

Top guest favorite
The entrance of the property is marked by a gated driveway, leading to a welcoming guest house surrounded by lush trees. The pathway is bordered by well-maintained landscaping, providing an inviting approach to the home.
Guesthouse in Milton
4.99 out of 5 average rating, 146 reviews

Siesta Cottage on the Blackwater

Looking for convenience to all of the Gulf Coast's treasures without breaking the bank? Have a boat or jet skis? Coastal guest house on 3 acre waterfront estate on Ward Basin/Blackwater Bay. Close to beaches, downtown Pensacola, and all of the natural wonders of NW FL. Nearby boat ramp, space for boat trailer, and ability to tie up to the dock on site. Sleeps four (queen bed and queen sleeper). No Pets - 2 min to I-10 -20 min to Navarre Beach -30 min to Downtown Pensacola

Top guest favorite
The stilt house features a wooden deck with seating options and overlooks the tranquil Blackwater River. Surrounding trees provide a natural setting, while the calm water reflects the structure and landscape. A boat dock is visible, enhancing the waterfront experience.
Home in Milton
4.95 out of 5 average rating, 223 reviews

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.

Top guest favorite
A master bedroom is presented with a spacious wooden bed, adorned with neutral linens and a striped blanket. Flanking the bed are two lamps on bedside tables, and a stylish ceiling fan provides airflow. A crib is positioned nearby, complemented by warm-toned curtains.
Home in Atmore
4.99 out of 5 average rating, 146 reviews

The "Home Over the Bridge"

Welcome to a place of comfort and ease with style. Kick back and relax inside or enjoy a cool star-lit night with friends and family around the fire. Nestled on two acres, “The Home Over the Bridge” is only a mile from downtown shopping, dining, and farmers market. If one is looking for a little fun and excitement the Wind Creek Casino and the Atmore Dragway are only 12 minutes up the road. The local splash pad and city parks are also only about a mile away.

Top guest favorite
The exterior of the home features a brick facade and a large covered carport. A spacious driveway leads to the front entrance, which is framed by manicured landscaping and tall trees in the background. The roofline accents the inviting structure under a partly cloudy sky.
Home in Brewton
4.99 out of 5 average rating, 148 reviews

The Dogwood - Luxury home

A cozy & luxurious home away from home. Living room & Each bedroom with TV. Master has king bed with separate tub and shower. Spacious open floor plan with electric fireplace. Covered back porch with great privacy & attached carport. Guest bedrooms have queen beds. New build which opened December 20,2019. Great location for those visiting family, on business or just a relaxing getaway. 1 adult/guest must be 25 years old to book this house.

Top guest favorite
A charming guest house is presented with a covered front porch featuring white railings. The building showcases a light exterior complemented by large windows that invite natural light. Surrounding trees provide a natural backdrop, emphasizing the serene outdoor environment.
Guesthouse in Milton
5 out of 5 average rating, 29 reviews

Little White House

Come stay in our guest house. While you are visiting beautiful Northwest Florida, enjoy Black Water River by tubing, rafting, and canoeing in our home town of Milton, or take a short drive to Pensacola Beach and enjoy restaurants, shopping, and tiki bars along with the whitest beaches on the Gulf of America. Pensacola is home to the Blue Angels and Blue Wahoos. Downtown has loads of entertainment from seafood & music festivals to fishing on the pier.

Superhost
A cozy corner is created with two stylish chairs positioned around a decorative table. Sunlight filters through three windows, highlighting the vibrant orange walls and providing views of the surrounding nature. Shelves on either side display plants and decorative items.
Apartment in Jay
4.78 out of 5 average rating, 9 reviews

Inspiring peaceful escape great 4 artist & writers

Escape to our serene 500 sq ft second-floor studio, perfect for nature lovers, writers, and artists. Enjoy a private deck overlooking 28 park-like acres with over a mile of walking trails, plus access to 14,000 acres of adjacent timberland. This well-equipped retreat features a full kitchen with granite counters, a cedar closet, and a cozy living space, ideal for extended stays. Embrace tranquility and inspiration at Under the Hoof.

Popular amenities for Jay vacation rentals

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