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Holiday houses in Madison

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Top-rated holiday rentals in Madison

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

Superhost

Tiny home in Carrabelle

4.86 out of 5 average rating, 209 reviews

The Sweet Peach - 2 Adults 1 toddler

This NOT so tiny, tiny home is located across from the bay, has everything needed to enjoy your vacation. Completely remodeled in 2017. Shabby chic, beach decor, Q sized bed, 2 stuffed chairs & complete kitchen. Screened in porch, dining area, chairs. Relax with a beverage & enjoy the amazing view of the bay. Affordable small family (2 adults 1 small child) vacation or romantic getaway. Professionally cleaned after each guest stay. Bathroom is small with corner shower. Pet policy in listing

Guest favourite

Home in Carrabelle

5 out of 5 average rating, 7 reviews

Cute New Resort Home Near Beach

Experience luxury living in this brand new fully furnished home within a golf and pickleball resort. Accommodate up to 8 guests and enjoy a perfect blend of relaxation and activity. Enjoy complimentary access to the community's private bayfront park, playground, and resort restaurant, with other resort amenities available at an additional charge (contact resort for pricing) – including brand new resort pool, 8 pickleball courts, bikes, fitness center, and 18-hole golf course with driving range.

Guest favourite

Home in Valdosta

4.92 out of 5 average rating, 49 reviews

Luxury Tranquility In The Pines

Nestled among the pine trees in a highly sought after neighborhood. This home is amazing 5 star accommodations with a modern country feel. Feel at home in this luxury home away from home. Close to everything. Just 2 miles off of I-75. 5 minute drive to everything from dozens of restaurants and shopping including Publix, Starbucks, Chic-fil-a, and the shopping mall. Open bright and airy floor plan. Large rooms, spacious backyard yard with large deck. TVs in every room and onsite EV charging.

Guest favourite

Home in Panacea

4.91 out of 5 average rating, 144 reviews

Fishermans Retreat

Fisherman's Retreat is the perfect location to get away from the stress of the city. Located in the heart of the quiet and cozy Panacea ocean community you are close to several beaches, boat ramps, favorite local fishing spots, kids playground across the street and our outstanding Gulf Specimen Aquarium that is fun for all ages. Plus, you can take in and enjoy several local restaurant that will satisfy every culinary appetite. So, check out of the big city and check into our relaxing home.

Guest favourite

Home in Alligator Point

4.95 out of 5 average rating, 64 reviews

Family Beach House | Steps to Sand & Shells | Pets

Discover this hidden gem on Florida's Forgotten Coast at our Updated &Fully Equipped Beach House just steps from a Private White Sand Beach. Perfect for your next family vacation, this beach house features: 5 bedrooms & 6 beds 3 baths Complimentary beach chairs & toys BBQ Smart TVs, & more! Relax on the screened porch or spend the day playing on the beach enjoying the peaceful and breathtaking natural surroundings. Book now to experience the ultimate beach escape @ SEAcluded Paradise!

Guest favourite

Home in Fort White

4.75 out of 5 average rating, 288 reviews

Santa Fe Getaway on Santa Fe River.

We are next door to Rum Island Park which is a swimming spring, kayak and canoe pick up/ drop off/boat ramp location. It is a private cottage. 1 bdr Sleeps 4. 1 Bedroom with a sleeper sofa. You’ll love my place because of the location. The river is in the backyard. You can launch your personal canoe or kayak. Sit by the fire pit or enjoy the deck and cook out with friends and family. We have a no pet policy due to our allergies. Town of High Springs and Gainesville near by

Guest favourite

Townhouse in Alligator Point

5 out of 5 average rating, 22 reviews

Alligator Point Bayfront Townhouse

"Drift Off Course" offers beautiful Views of the Bay! This home is a true Boaters Delight - offering boat access at the Marina or right behind the house. It's also sure to please those who love the beach. Enjoy a private strip of beach area of the bay or an easy walk over to the gulf. With a location that can't be beat - walking distance to the boat ramp, Alligator Point Marina, deeded access to the Beach across the street with multiple views of the beach, bay and the marina.

Superhost

Cottage in Thomasville

5 out of 5 average rating, 4 reviews

Cottage with private outdoor oasis

Whether you are in town for business or visiting family this private oasis will be your favorite home base. Recently remodeled, this home has amazing upgrades in the kitchen. 2 perfectly sized bedrooms (1 King, 1 Queen) and an incredible outdoor space. The home has been tastefully decorated and is well stocked with everything you will need. 1,344 square feet inside, includes a sunroom with a dedicated work space, and private outdoor seating for a retreat like no other.

Superhost

Home in Carrabelle

4.93 out of 5 average rating, 84 reviews

The Bella Beach Treehouse: New Pool. Kayak. Golf

A beachfront home nestled among the trees with a new private pool addition March 2023. Enjoy your own private retreat on the Forgotten Coast, known for spectacular fishing, scalloping, kayaking, hiking. Golf course is only a minute away. Fish from backyard or relax on hammocks among the trees. Sandy beach perfect for sunbathing or creating memories around a beach fire. Parking for boat/RV. Gogeous pcean views from the living/dining room, bedroom and deck.

Superhost

Cottage in High Springs

4.91 out of 5 average rating, 141 reviews

Beautiful Cottage close to town,springs and rivers

Beautiful high springs cottage close to town and the amazing local springs and rivers. Completely remodeled cottage with all new EVERYTHING! Beautiful new furniture and very comfortable beds. Several local springs and rivers just minutes away: Poe springs 6 minutes Blue springs 13 minutes Ginnie Springs 13 minutes Canoe / kayak the Santa Fe river 5 minutes Ichetucknee (tubing) springs state park 20 minutes Rum Island park 15 minutes

Guest favourite

Campervan/RV in Panacea

4.92 out of 5 average rating, 122 reviews

The Panacea Palace

RV conveniently positioned with dock and bay access. Fishing, kayaking, and hiking right outside your front door. Boat slip available and seven public boat ramps within a 5-mile radius. Daily sunset cruises for an additional fee, and boating excursions can be booked on weekends and select weekdays. This high-end camper has all the luxuries of a waterfront resort without the waterfront premium. Paradise awaits.

Guest favourite

Home in Tallahassee

5 out of 5 average rating, 132 reviews

Sienna Lee Gardens: A Beautifully Renovated Home

Relax and unwind in this beautifully renovated 4 bedroom/3 bath home nestled on 20 acres of picture perfect live oaks, organic blueberry orchard, and abundant wildlife. There are so many places for entertaining including a large heated swimming pool (heated from March-Nov). There's a fully equipped kitchen, luxury beds and hotel quality linens. Every room has cable TV and internet throughout the house.

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Madison holiday rentals

Kitchen
Wi-Fi
Pool
Free parking on premises
Air conditioning

Stay near Madison's top sights

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

Other great holiday rentals in Madison

Guest favourite

Home in Lake Park

4.99 out of 5 average rating, 130 reviews

Lakefront home. sleeps 4- 1 bedroom 1 bath

Guest favourite

Home in Tallahassee

4.9 out of 5 average rating, 20 reviews

Fantastic Gem Minutes from Campus/Stadium, Capitol

Guest favourite

Guesthouse in Crawfordville

5 out of 5 average rating, 53 reviews

White Squirrel Cottage

Superhost

Home in Fort White

4.86 out of 5 average rating, 14 reviews

Golden Girls Spring Retreat 2

Guest favourite

Home in Saint Teresa

4.92 out of 5 average rating, 59 reviews

Cozy coastal cottage w/pool and dogs are welcome!

Guest favourite

Home in Hahira

4.97 out of 5 average rating, 68 reviews

Cozy Cottage in Convenient Hahira Location

Guest favourite

Home in Live Oak

4.9 out of 5 average rating, 61 reviews

Northern Florida Country Home

Guest favourite

Home in Valdosta

5 out of 5 average rating, 7 reviews

Close to town Farmhouse

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