Vacation 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

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!

Delightful 5th Wheeler with covered open air deck.

5th wheeler nestled under a pole barn making it 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. This is an operational ranch. All adults are required to sigh the Florida Argitourism Liability Law wavier. Hosts live on the property but does not face the RV. Come and go as you please. Watch the sunsets or look at the night sky. Hope to see you soon!

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!

Hannah Jane's Haven

This memorable place is anything but ordinary. If you are looking for a quiet place to experience serenity and tranquility, this is it! This property offers a gorgeous space that sets the stage for relaxation and fosters an environment to help you recharge while enjoying all that nature has to offer. This triple terraced property offers many ways to rest and find balance in nature. From nature walks to kayaking, to outdoor grilling and bonfires. We invite you to come...relax and unwind!

Upper Bunkhouse on Beaty Ranch

Beaty Ranch’s bunkhouse will be sure to quiet the noise for some quality R&R in the country. Our main bunkhouse offers you a queen & full size bed, twin bed and sofa along with a full bathroom, coffee bar and more. Major towns & state parks nearby! Convection oven, refrigerator & BBQ grill available too. If you are wanting to unplug from your day to day rush, come to our North Florida oasis where you can watch the horses and cattle graze and see all the stars sparkle.

Cozy Farmhouse w/ spacious decks

Welcome to our peaceful home on 6.5 acres! Located 10 minutes from I-75, exit467. There's ample parking for large and/or multiple vehicles and trailers. Close to it all, with room to roam. Unwind while relaxing 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 grill out on the patio. There's a little something for everyone!

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.

Guest House in the Country

Nestled in over 100 acres of wooded farmland near Madison FL. Recharge and reconnect with nature on this private unforgettable property. This Guest House is the ultimate getaway for up to 3 yearning for life in the country. Experience the peace and rhythm of nature and farm living. Spend quality time with that special someone while taking in a sunset or looking up at the wonder of the Milky Way.