Vacation rentals in Madison

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Top-rated vacation rentals in Madison

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Tiny home in Live Oak

4.99 out of 5 average rating, 406 reviews

KT’s Cottage Tiny Home near the Suwannee River

KT’s Cottage is located just minutes outside the city limits of Historical Downtown Live Oak and the beautiful Suwannee River. If you are passing through for business or to enjoy the area, I hope you will find our cottage’s accommodations are more than satisfactory. There is a queen bed downstairs as well as a queen in the loft, with plenty of extra pillows and blankets for your comfort. Coffee, tea & bottled water are included. Enjoy grilling while relaxing in the swing or sitting by a campfire

Feb 20 – 27

$92 per night
Guest favorite

Cabin in Live Oak

4.92 out of 5 average rating, 102 reviews

Florida Country Cabin Getaway

Nestled in the heart of rural North Florida, this picturesque log cabin on 3 acres offers a tranquil retreat enveloped by majestic oaks and towering pines. Stepping inside, they find themselves embraced by the warmth of a cozy interior, where comfortable furnishings invite relaxation. However, the true allure lies where a sprawling outdoor deck beckons guests to unwind amidst the serenity of nature while enjoying their morning deink from the extensive selection of coffee, tea and hot chocolate.

Jul 16 – 23

$259 per night
Guest favorite

Shipping container in Live Oak

4.96 out of 5 average rating, 222 reviews

Nature lover/Artist cabin peaceful Rescue Farm

Kokomo has a variety of unique accommodations including a tree house, tiny house, yurt tent, Shipping Container house, Hanging round bed glamping room & more just click on my profile picture to see all . Visit our barnyard rescue animals, relax in the Zen garden hot-tub, play yard games, paint the artwall, enjoy a community fire pit, relax in the enchanted forest hammock, or walk a trail. Try our stargazing bed to Experience a beautiful starlit sky and wakeup to the sounds of nature all around.

Nov 22 – 29

$112 per night

Popular amenities for Madison vacation rentals

Stay near Madison's top sights

Winn-Dixie3 locals recommend
Rancho Grande Mexican Restaurant6 locals recommend
Cucinella's Brick Oven Pizzeria3 locals recommend

Other great vacation rentals in Madison

Superhost

Tiny home in Jasper

4.81 out of 5 average rating, 108 reviews

Deer Park Cabin

Sep 6 – 13

$81 per night
Guest favorite

Home in Mayo

4.95 out of 5 average rating, 319 reviews

Small Town Charm & Living

Feb 10 – 17

$104 per night
Guest favorite

Cabin in Pavo

4.97 out of 5 average rating, 233 reviews

Cabin on Lake Nichols

Dec 6 – 13

$175 per night
Guest favorite

Cabin in Fort White

4.93 out of 5 average rating, 264 reviews

Log Cabin in Spring Country WiFi - TV

Mar 25 – Apr 1

$84 per night
Guest favorite

Home in Branford

4.96 out of 5 average rating, 269 reviews

Papa Joe’s Lake House

Aug 7 – 14

$93 per night
Guest favorite

Tiny home in Alachua

4.96 out of 5 average rating, 251 reviews

Ela's Tiny House: Springs, Trails & Disc Golf!

Jun 29 – Jul 6

$62 per night
Guest favorite

Guesthouse in O'Brien

4.83 out of 5 average rating, 414 reviews

River Retreat

Nov 27 – Dec 4

$60 per night
Guest favorite

Cottage in Monticello

4.96 out of 5 average rating, 110 reviews

The Cottage at Grand Oaks Plantation

Mar 22 – 29

$228 per night
Guest favorite

Apartment in Monticello

4.94 out of 5 average rating, 18 reviews

Private 2 Bedroom Cabana w/ Pool View

Apr 17 – 24

$82 per night
Guest favorite

Place to stay in Pinetta

4.9 out of 5 average rating, 63 reviews

A piece of heaven on Cherry Lake

Mar 19 – 26

$77 per night
Guest favorite

Camper/RV in Madison

5.0 out of 5 average rating, 5 reviews

Glamping at its finest! Private 1 BR, A/C, Wifi.

Jul 12 – 19

$68 per night
Guest favorite

Guesthouse in Live Oak

5.0 out of 5 average rating, 40 reviews

Cozy Studio Retreat

Sep 9 – 16

$99 per night

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