Vacation rentals in Havana

4.96 out of 5 average rating, 108 reviews

Apartment in Tallahassee

Like New Midtown Retreat | 3 TVs • Ethernet Port

This is a newly renovated 2BR 1 Bath apartment on the first floor located central off Meridian, a Canopy Road, in Tallahassee, just a short ride or walk to shopping, Whole Foods, Riccardos, ABC, Publix, Walmart, Food Glorious Food, Winthrop Park, Planet Fitness and hundreds of nearby restaurants and coffee shops, Near John Knox and the Trousdell Aquatics Center. These units come with over the top line beds, 3 Tv's and fast internet-20 minutes to just about anywhere in Tallahassee. Pool 0.9 mi.

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5 out of 5 average rating, 14 reviews

Lake Talquin Waterfront Lakehouse on Forest Border

Relax at this peaceful Lake Talquin lake house with a 130 ft. waterfront, gorgeous views and private dock and boathouse for direct lake access. This spacious 3BR/3BA home features an open living area, full kitchen, fast Wi-Fi, and outdoor space ideal for fishing, kayaking, and sunset lounging by the fire pit. Bordered on one side by Talquin State Forest, enjoy this lakeside retreat where you rarely hear or see anything but nature. Just 25 min. to Tallahassee. Perfect for families or remote work.

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Guesthouse in Tallahassee

The guest house is nestled in a lush green setting, featuring a large screened-in porch illuminated by soft outdoor lighting. The exterior displays a blend of dark wood and light accents, with a welcoming entrance door and surrounded by well-maintained garden space.

4.87 out of 5 average rating, 385 reviews

Beautiful Guest House in Desirable Northside

Hello and welcome to our home! This guest house is in our backyard and is very cozy with a large, screened-in porch. Sit in a rocking chair on the porch and enjoy the sounds of the many birds and the company of butterflies and hummingbirds. The King size bed is so comfortable! Our neighborhood lies between the Market District to the south and Bannerman Crossing to the North. There is shopping as well as many restaurants all around us. Downtown and FSU are 20 min away depending on traffic.

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4.89 out of 5 average rating, 27 reviews

Loft in Havana

Stunning Historic Building Lofts! Meet Bricks!

Welcome to Bricks, a 2-bedroom, 1-bathroom loft in the ❤️ of downtown Havana! Just 15 minutes from Tallahassee, 20 minutes from Bainbridge, and light-years away from ordinary. This 1,500-square-foot gem boasts 12-foot ceilings, heart pine floors, and original brick walls that ooze charm. Now, fair warning: to reach this masterpiece, you’ll tackle 21 stairs—consider it your warm-up for the day. The entrance is off a main road, so expect a little traffic noise. It’s all part of the experience!

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5 out of 5 average rating, 22 reviews

The charming exterior of a craftsmen home is showcased, featuring a spacious porch with an American flag. The house is painted in light blue and white, complemented by decorative architectural details. Lush greenery and a stone pathway enhance the inviting atmosphere.

Home in Havana

Quaint Craftsman Downtown Havana

Nestled on the outskirts of downtown Havana, our home offers a quaint escape just a 5-minute stroll from charming storefronts. Enjoy local gems like Gocki’s burgers, Oscar’s Italian Eatery, and Off the Rails Irish Pub. Antique enthusiasts will love The Twisted Pineapple. Alongside Havana's unique blend of small-town charm, there is a grocery store and fast-food chains. Only 15 miles from downtown Tallahassee, relish the Hallmark feel of Havana while having easy access to big-city amenities.

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4.94 out of 5 average rating, 103 reviews

Cottage in Havana

Guesthouse - Studio in the woods

The guesthouse sits tucked back in the woods next door to our home, offering privacy and quiet once you arrive. The surrounding area is rural and unpolished - but the property itself is clean, peaceful, and thoughtfully maintained. Check-in is between 3:00 pm and 11:00 pm EST. We do not allow check-ins after 11:00 pm. This property is not suitable for anyone with mobility issues or who is unsteady on their feet. No smoking, e-cigs, or vaping permitted in the cottage or on the property.

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4.97 out of 5 average rating, 324 reviews

The front porch features a swinging bench adorned with a decorative yellow cushion. A potted plant sits beside the door, which is made of wood and includes brass fittings. Sunlight filters through the trees, casting a warm glow onto the light blue floorboards.

Home in Bainbridge

Little House on Broughton Downtown Bainbridge Stay

Located just four blocks from beautiful downtown Bainbridge, this one bedroom, one bath historic shotgun house was recently moved to Broughton Street from across town and fully renovated by your host. Enjoy a taste of an original tiny home with big personality! Home includes free wifi, fully equipped kitchen, and tips from your host on favorite local stops. Pet friendly stay perfect for walks through historic downtown Bainbridge for pets under 50 pounds with a $75 pet fee.

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A single-story house is framed by lush green trees and a well-maintained lawn. The home features a bright yellow front door, and a driveway leads to the garage. Fencing is visible in the backyard area, promoting privacy.

4.86 out of 5 average rating, 545 reviews

My House, Your House

This home away from home is the perfect place to lay your head after a long day from traveling. Whether you're here for homecoming or traveling for work, our home is nestled in a quiet community a short drive from local restaurants, shops, hospitals and the local Universities. The space includes 3 fully furnished bedrooms, coffees and teas. We also provide everything you need to cook and serve a meal. Access to washer and dryer. We are local and available if needed!

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Superhost

4.91 out of 5 average rating, 43 reviews

Tranquil Retreat w/ Modern Flair

Discover serenity in our sleek woodland haven, where modern elegance meets natural charm. Upgraded fixtures and stone counters adorn this retreat, while the screened front and spacious rear porches offer al fresco dining and relaxation opportunities. Indoors you'll enjoy the cozy wood-burning fireplace and vaulted ceilings, lending a bright and airy charm. Remodeled baths await before you retire to large bedrooms, each boasting a work desk and spacious closets.

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4.98 out of 5 average rating, 134 reviews

King Bed-Pets -Quiet-Huge fence Yrd

Unwind in this spacious, equestrian-themed retreat in a peaceful upscale country setting! Set on a large fenced lot, this dog-friendly home offers comfy new beds, Roku TVs in every bedroom, and all the amenities you’d expect. Enjoy shuffleboard, gather outdoors, or relax with easy access thanks to the 2-car garage with remote. Plenty of room to roam and recharge—perfect for a serene getaway just outside the city buzz.

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Guesthouse in Tallahassee

The exterior of the Little Green Guest House showcases a charming green facade and classic architectural features. A covered carport is present on one side, surrounded by well-maintained landscaping and mature trees, contributing to a serene residential setting.

5 out of 5 average rating, 84 reviews

Lovely guesthouse with outdoor space/near I10

The Little Green Guest House is ideal for business travelers, families, university parents, or sports fans. 1BR/1BA with full kitchen offers total privacy and all the comforts of home. Located in a quiet neighborhood in NE Tallahassee on the grounds of a beautifully maintained 1920’s home, the Little Green Guest House is 15 minutes from the universities, very convenient to retail and dining, and minutes to I10.

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