Vacation rentals in Monticello

A wooden boardwalk leads to the beach, framed by two benches on either side. The ocean is visible in the distance under a clear blue sky, with sunlight shining directly overhead.

5 out of 5 average rating, 11 reviews

La Mer - Beachfront Condo, Saint George Island, FL

Enjoy our 5 Star Island Lifestyle Beachfront Condominium. New curated comfort décor with stunning views of our award-winning Gulf beaches. Centrally located, the Villas of St. George is close to shops, restaurants, nightlife, Lighthouse Museum and playground, fishing pier, State Park, and food trucks. With Private Community pool, parking & boardwalk direct to sugar sand shores. Sleeps 8: Pull out sleeper sofa(King), 1 King, 2 full, 1 twin(trundle). Sorry Pets are not allowed at this property.

4.86 out of 5 average rating, 212 reviews

Tiny home in Carrabelle

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

A covered porch features vibrant blue chairs arranged around a circular table, offering views of the ocean and surrounding greenery. The sky is bright with clouds, enhancing the tranquil setting, while nearby buildings provide a sense of the coastal community.

4.75 out of 5 average rating, 8 reviews

The Sand Bar

The perfect beach retreat! Located in the SGI Plantation, spacious but also welcoming for only a few guests. Sits directly across from the beach and offers amazing unobstructed views Tastefully decorated, offers granite countertops, new appliances, and upscale furnishings. Recently remodeled outdoor kitchen offers a dining area, large gas grill, mini fridge and counters for food prep The rest of the outdoor area features a hot tub, TV, private pool, enclosed outdoor shower and fish cleaning area

5 out of 5 average rating, 8 reviews

An open-concept kitchen and dining area features a large island with a dark granite countertop and stainless steel appliances. A wooden dining table with benches invites gatherings, while windows allow natural light to illuminate the space. Neutral grey walls and hardwood flooring enhance the welcoming ambiance.

Home in Carrabelle

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.

A large, furnished screened porch features a blend of seating areas, including a table with chairs and a casual lounge space. A neutral-toned rug complements the warm wooden flooring. Steps lead from the porch to the outdoor area, providing easy access.

5 out of 5 average rating, 5 reviews

Redfish: view, pool, steps2beach

Just over the dune line road from quiet east end beaches. Great fishing and uncrowded relaxing . Excellent for families or couples (4 person maximum) with private spaces indoor and out. Two master bedrooms with kings and pillow tops. Second floor cottage recently remodeled and decorated. Shared pool and gulf views from front room and master. Front Deck. Large furnished screened porch. You will be hard pressed to find a better spot for your vacation dollars. Beach wagon, umbrella and chairs.

4.92 out of 5 average rating, 161 reviews

A single-story home features a welcoming front porch with green railings and a decorative entrance. A light color palette of the exterior is complemented by green shutters, and tall palm plants line the front yard, creating an inviting outdoor space surrounded by natural landscaping.

Home in Panacea

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.

4.91 out of 5 average rating, 56 reviews

A modern kitchen features dark cabinetry and light countertops, creating a stylish contrast. An island with seating is situated at the center, accompanied by a dining area with four bar stools. Warm lighting highlights the open layout and wood flooring.

Home in Valdosta

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

4.98 out of 5 average rating, 48 reviews

An outdoor screen porch is featured, showcasing a wooden table and comfortable seating. A kitchenette with a stainless steel sink and multiple appliances is visible, alongside a ceiling fan for airflow. Natural light filters in, highlighting the wooden flooring and surrounding greenery.

Home in Steinhatchee

Tortuga Getaway with free ice,

Tortuga Getaway is located in the heart of town. Comfortably sleeps 10. Ideal for friends or fishing nuts. BONUS: free ice, saving you the trouble of stocking up. 3 BR, 3 BA ensure every guest has privacy. Spacious rooms and a well-stocked kitchen. Features an inviting screen porch, perfect for relaxing outdoors. For boaters, convenient parking makes it hassle-free. If you're a fishing/scallop enthusiast, you're in for a treat. Steinhatchee is the best fishing/scalloping spot in Florida.

4.98 out of 5 average rating, 101 reviews

Home in Panacea

Paradise Point! Direct Beachfront Florida Oasis!

Paradise Point is a Direct Beach front home perched on the shores of the Gulf of Mexico! This rare to find Beach House embodies relaxation and solitude. The white sand beach of Florida’s Forgotten coast is just out front. One of the most incredible locations for miles, the views and peacefulness are unrivaled. This is an elevated and updated Beach home with a Brand new appliance suite, custom granite counters & more updates. Wake to the sounds of waves on the beach just outside your door.

5 out of 5 average rating, 5 reviews

A screened-in porch features a ceiling fan and a tiled floor. Natural light fills the space through windows, creating a bright and airy atmosphere. A view of the private yard is visible through the porch's openings, enhancing the connection to the outdoors.

Home in Steinhatchee

Cutest and one mile to fishing, boating, & marina

Escape to Florida's tranquil Big Bend at 'Seagrass Cottage'! This 4-bedroom, 3-bathroom Steinhatchee vacation rental sits in the heart of a fishing village that's teeming with small-town charm and diverse aquatic species. At this coastal home base, you can spend days on the river or visit natural springs - whatever floats your boat! Once you get your land legs back, don't forget to hike to Steinhatchee Falls, local seafood at Sea Hag, or relax in the bug-free comfort of the screened porch!

5 out of 5 average rating, 8 reviews

A modern kitchen features light gray cabinets and a spacious wooden island with seating. A farmhouse sink is positioned beneath a large window, allowing natural light. Neatly arranged dishes and glassware are displayed on open shelves, contributing to a functional and inviting cooking space.

Cottage in Thomasville

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.

A bright living area features comfortable blue and cream seating arrangements. Two large windows allow natural light to flood the space, framing views of greenery outside. A colorful coffee table sits in the center, complemented by a wooden stool, adding a touch of natural texture.

5 out of 5 average rating, 26 reviews

Island Adventures Await at the “Boathouse SGI”

NEW POOL & FENCED YARD! Newly renovated! Looking for a getaway to the Island that boasts the accolade “2023 #1 Beach in the US”? Begin your adventures at The Boathouse! Located on the island's golf cart-friendly west side (but still near the center of town) you’ll be close enough to walk to the Lighthouse, 1.5 blocks from the bay & 4 blocks to the ocean. From the expansive windows, view includes a tad of the bay, reminding you that the bigger bay and gulf are calling.

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Stay near Monticello's top sights

Rev Cafe3 locals recommend

Monticello Opera House, Inc.4 locals recommend

Tupelo's Bakery & Cafe4 locals recommend

Other great vacation rentals in Monticello

5 out of 5 average rating, 5 reviews

Home in Steinhatchee

Fish Tales Townhome - Units A & B

4.85 out of 5 average rating, 59 reviews

A private screened pool area is visible, featuring clear blue water and a spacious pool deck. Comfortable lounge chairs are arranged around the pool, with a dining set nearby. Lush greenery and bay views are seen in the background, enhancing the tranquil setting.

Home in Eastpoint

Bayft home w pvt pool near SGI C’belle & Apalach

A covered porch features light wooden flooring and soft pink walls. Two white rocking chairs are positioned beside a small table with bright green chairs. Large windows allow natural light to enter, with an open doorway leading to the interior of the home.

5 out of 5 average rating, 11 reviews

Beach Baby

A serene sunset reflects off the calm waters of a lake, casting warm hues of orange and gold. Silhouetted figures can be seen on a floating structure, enjoying the tranquil scene as the sky transitions into dusk.

Home in Lake Park

4.74 out of 5 average rating, 124 reviews

Lakefront Paradise with Amazing Sunsets

4.89 out of 5 average rating, 37 reviews

A welcoming park entrance is marked by a wooden sign that reads 'Welcome to Island View Park.' The scene features two open pavilions with metal roofs, overlooking a tranquil waterfront. Sunlight reflects on the water, enhancing the serene atmosphere of the park.

Home in Carrabelle

The Snapper House

5 out of 5 average rating, 139 reviews

Home in Tallahassee

Sienna Lee Gardens: A Beautifully Renovated Home

5 out of 5 average rating, 23 reviews

A private beachfront home is depicted, featuring a wide deck with multiple windows and palm trees surrounding the property. A wooden walkway leads from the sandy shore to the entrance, highlighting the home's proximity to the water.

Home in Carrabelle

Coastal Adventures Waterfront!

An aerial view showcases the proximity of the property to the beach, indicated by a clear path through the surrounding greenery. The tranquil coastline stretches in the background, while several beach houses are visible along the shore.