Vacation rentals in Jay

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Top-rated vacation rentals in Jay

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Top guest favorite

A wooden deck features two rustic rocking chairs, inviting relaxation. The entrance of a cozy cabin, adorned with a red door, is framed by large windows. Surrounding pine trees provide a natural backdrop, creating a peaceful outdoor space.

Guesthouse in Jay

5 out of 5 average rating, 30 reviews

The Bunkhouse & Bathhouse a unique farm experience

Nestled on 28 picturesque acres, Under the Hoof Farm is a vibrant haven for animals and nature enthusiasts. Here, you'll encounter a delightful mix of goats, chickens, dogs, and gopher tortoises, all coexisting harmoniously. As a proud Stewardship Forest, Certified Tree Farm, and designated gopher tortoise habitat, we are committed to sustainable land management and wildlife conservation. Come visit us and experience the farm, where every day brings adventure and a deeper connection to the land

Guest favorite

A full-size pool table is centered in the room, illuminated by pendant lights above. The walls feature a light brown color with a horizontal blue stripe. A tall wooden chair is positioned near the door, and a window is adorned with patterned curtains.

Guesthouse in Brewton

4.88 out of 5 average rating, 73 reviews

The Best Guest House

Located above a detached garage, The Best Guest House is a unique space. A full size pool table welcomes you as you walk through the door. When you walk to the back, you'll find the kitchen which has a vintage stove that adds a cool touch to the modern decor. Look for a "secret" door and you'll find the bedroom space tucked behind the door. Guest House is located in the small southern town of Brewton, just 60 miles from the beautiful Florida Gulf Coast and 90 miles from the Alabama Gulf Coast.

Top guest favorite

A yurt-style tent sits on a wooden platform surrounded by trees. The tent features a large mesh opening and is accompanied by a picnic table nearby. Solar string lights illuminate the area, enhancing the secluded outdoor setting.

Yurt in Milton

5 out of 5 average rating, 66 reviews

The Wandering Path Yurt #3

Immerse yourself in nature with over 20 wooded acres and 2000 feet of water frontage and trails on Big Coldwater Creek. Quiet, tranquil and peaceful are how most guests describe their stay at The Wandering Path. Being in nature has a significant impact on mental and physical health. You will leave here feeling refreshed and recharged. Kayak, canoe, hike, fish or relax the day away. At this time, children under 12 are not allowed, pets are not allowed, exceptions are considered,Pls inquire

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

4.99 out of 5 average rating, 99 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 charming renovated home is displayed, featuring a blue exterior with white trim. The front porch is enclosed with multiple windows, allowing for ample light. Surrounding greenery adds a natural touch, and steps lead to the welcoming entrance.

Home in Brewton

4.95 out of 5 average rating, 21 reviews

Mady's Happy Place

Please make yourself at home in our cozy renovated nearly 100 year old home. Just minutes from historic downtown Brewton, parks, shopping and restaurants. Plan a day trip to the pristine white beaches in Pensacola located just 1 hour and 15 minutes away. Then head back to your warm and inviting home to enjoy the sunset on the enclosed porch or just curl up on the couch in front of the 65" TV. Whatever you decide to do, Mady's Happy Place is here to make your getaway a wonderful experience.

Top guest favorite

Home in Pace

4.94 out of 5 average rating, 205 reviews

THE PINE HOUSE *September Specials*

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

A wooden deck extends from the tiny home, featuring two turquoise lounge chairs. A single entrance door is visible, complemented by surrounding greenery in the background, adding a sense of tranquility to the outdoor space.

Tiny home in Milton

4.91 out of 5 average rating, 112 reviews

Tucked Away Tiny

Reconnect with nature at this unforgettable escape. The “Tucked Away Tiny” is a tiny home with HUGE style! It is located in the country woods of Milton, FL on family-owned farm land, but not too far off the beaten path. Only 15 minutes to the heart of the city, and 45 minutes to beaches. It is next door to Sowell Farms which is home to several wedding venues, fenced exotic wildlife (may or may not be seen during your stay), and home of the Trophy for Great American Christmas Light Fight!

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

4.96 out of 5 average rating, 187 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

An open-plan living area is displayed, featuring a cozy sleeping space with a spacious bed, surrounded by large windows adorned with floral curtains. A table with several chairs is situated next to a small kitchenette, while a rocking chair adds to the rustic charm.

Farm stay in Walnut Hill

4.99 out of 5 average rating, 165 reviews

The Cottage- Seales Farm

The Cottage is located on Seales Farm- a working cattle farm with views of pastures, grazing horses and some unusual sounds (guineas and lowing cattle.) This pastoral and rustic setting offers solitude- NO TV and NO WiFi . - There is a private outdoor seating area with a great view. We are a little more than an hour from Pensacola Beach, Fl. which boasts historical Fort Pickens and 75 miles from Gulf Shores, AL. Wind Creek Casino just 20 minutes away.

Top guest favorite

A spacious outdoor area is enclosed with a framed structure, featuring soft blue and white lighting along the floor. Potted plants add a touch of greenery, while lounge chairs are neatly arranged within the space, providing a relaxing ambiance for outdoor gatherings.

Tiny home in Pensacola

4.98 out of 5 average rating, 165 reviews

Tiny Home Pool View 25 Mins to Beacha

Welcome to our cozy tiny home located in my secured backyard, where a queen-sized bed promises a peaceful night’s sleep and our well-equipped kitchenette simplifies meal preparation. You will have free parking in the backyard located just steps away from the tiny home. Additionally, you’ll have the opportunity to gather around the outdoor fire pit for cozy evenings under the stars. Inside, unwind with a smart TV and stay connected with complimentary Wi-Fi.

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, 132 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 fire pit area is surrounded by several wooden adirondack chairs on a gravel surface. The structure features a covered patio, with a red exterior visible in the background. Lush green grass and a white fence border the property.

Barn in Molino

4.96 out of 5 average rating, 84 reviews

The Coop@FtPeckens a Charming Rustic Barn Studio

Escape the city life and relax at our charming rustic barn studio under the stars. The coop @ Ft. Peckens is 200' behind the real Ft. Peckens. (the chicken coop). It's located in a very quiet and friendly country neighborhood and only 30 to 45 minutes away from the white sandy beaches of Pensacola, Florida. End your evenings on a high note with some smores around the campfire and kick back and watch the beautiful country sunset. Relaxation awaits!