Holiday rentals with outdoor seating in Madison County

Peaceful cabin on the Cochee River w/ 4 acres land

Come cookout, relax, fish & kayak (included) alongside the Withlacoochee River, freshly updated home on stilts is located just 15 min upriver from the Suwannee state park & hidden springs, the elevated back deck sits 10 ft from the riverbank. The 4-acre property boats plenty or mature oaks and pines w/ an old railroad bridge pillar making for amazing photos. Property frequently visited by deer, owls, & turkey. Private drive offering plenty of privacy & just 25 min from Live Oak shopping district

Just Blew Inn

This 2 bedroom home has 3 beds total 1 Queen 1 full n 1 twin long It is a quaint little house ,stone built , just three houses from the back gate of in Dowling Park Fl and less tan 1/2 mile to the Suwannee River in a very safe neighborhood . The Suwanee offers swimming kayaking, fishing and Boat rides only to mention a few. The property is over an acre with a carport, washroom with a washer and dryer It’s away from the traffic, a quiet area just three houses from the Advent Christian Village

A-frame near Madison Blue Springs

Get away from it all when you stay under the stars. Our A-frame Hobbit House is cozy and dry and sleeps 2 . The Aframe has electricity and AC in the summer months and heater for the cooler months. There is an outdoor bathhouse that is shared with the other people on the property. Outside, there is a picnic table, chairs, gas grill with burner, and firepit. You are welcome to use the firewood found on our property. Please note we have two very friendly golden retrievers and chickens on property.

Charming 2 Bedroom 2 Bath , Private Cabana

Escape to our cozy, fully furnished 2-bedroom home with queen beds—yours to enjoy in complete privacy! Unwind on the screened porch with stunning views of North Florida’s pastures and rolling hills. Enjoy peace and comfort with private parking and entrance. Fully equipped for your stay, it's the perfect blend of relaxation and adventure. Just 9 miles east of Monticello and close to outdoor fun like hiking, kayaking, and more! Enjoy our lake views , it’s the perfect spot to unwind and recharge!

Private updated Cottage, Cozy and Spacious

Escape to this charming, private 1-bedroom cottage with a queen bed and spacious living area—perfect for two! Enjoy stunning lake and orchard views from your cozy retreat, complete with a private picket fence, entrance, and patio area for outdoor relaxation. Fully equipped with all the comforts you need for ultimate peace and quiet. Just 9 miles east of Monticello, 20 minutes from Thomasville, and 35 minutes to Tallahassee. Unplug, unwind, and make unforgettable memories in this nature haven!

Lower Bunkhouse on Beaty Ranch

Our quaint lower bunkhouse will be sure to silence all distractions and connect you with quality rest and relaxation. Beaty Ranch is a working ranch with wide open spaces, beautiful sunsets and all the stars you want to see. Located just under an hour from Tallahassee and 20 minutes from Valdosta, we have the convenience of town without being in the middle of it. State parks are nearby too! Come unwind and watch the horses and cattle graze, read a book or just listen to the wind in the trees.

RV Retreat

**Cozy RV Retreat on 14-Acre Family Farm** Nestled on a peaceful 14-acre farm near Blue Springs State Park, this fully loaded 34-ft RV offers a perfect peaceful getaway for nature lovers. Enjoy swimming, diving, kayaking, and fishing at Blue Springs, or explore nearby biking, horseback riding, and birding trails. Visit historic downtown Madison or the Edge of Town in Lee for fantastic antique shopping and a cold brew at the Bullpen. Ideal for relaxation, book your quiet adventure today!

Cozy 3 BR FarmHouse, Decks & Fire Pit - SorelleBnB

Our home is located off the beaten path, on 6.5 peaceful acres. There's a lot of local wildlife to keep you entertained, from curious peacocks, to tortoises, bunnies, and deer. Sit back, pour a cold drink, and relax on the back porch listening to the birds and wind chimes. Create lasting memories playing nostalgic boardgames in the loft, or enjoy the outdoors by having a fun evening playing giant Jenga and roast marshmallows over the fire pit. There's a little something for everyone!

Blue Spring Hideaway

Reconnect with nature at this unforgettable escape. Just 0.1 mile from Florida’s breathtaking Madison Blue Spring State Park and the Withlacoochee River, this private, gated RV stay is your home base for nature, comfort, and adventure. The cozy RV sleeps up to 4 guests. Bringing more than four people? No problem. You’re welcome to pitch a tent on the property. Relax in the included saltwater jacuzzi, eat at the picnic table, and gather around the fire pit — firewood provided!

Delightful 5th Wheeler with covered open air deck.

5th wheeler nestled under a pole barn making the 5th wheeler cooler in the summer and warmer in the winter. It has a very nice open air deck and it situated on a working farm. One might see cows grazing in the fields or hear the chickens across the way! Hosts live on the property but house does not face the RV. Come and go as you please. Watch the sunsets or look at the night sky. This is a very comfortable RV! Parking is right at the door. Hope to see you soon!

A piece of heaven on Cherry Lake

A piece of heaven at Cherry Lake will have you feeling heavenly during your stay! On the waterfront property sit a two bedroom, one and a half bath trailer that has the feel of a cozy home. Dogs welcome with a one time pet fee. Cherry Lake is located in Madison County, south of Valdosta GA. The city of Madison has a historic district and one of the cutest downtowns in Florida lined with antique shops and locally owned eateries.

Cherry Lake Serenity - A Lakefront Retreat

A lakefront escape on Cherry Lake, Madison, FL. This custom home blends modern comfort with lakeside charm—perfect for families, couples, or friends. Enjoy sunrise views, coffee on the porch, or days spent fishing, kayaking, or boating from the private dock. End your evenings by the firepit or in the hot tub under the stars. Cherry Lake’s clear, spring-fed waters offer the perfect mix of relaxation and adventure.