Vacation rentals in Havana

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Top-rated vacation rentals in Havana

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

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Superhost

The exterior of a historic red brick building is visible, showcasing unique architectural details. Large windows allow ample natural light to enter. A vibrant mural depicting a train enhances the facade, while street elements like traffic lights and crosswalks are positioned nearby.

Loft in Havana

Stunning Historic Building with Lofts! Meet Brass!

This unique 2 bedroom, 1 bathroom loft is located in the heart of Havana. Just 15 minutes outside of Tallahassee and 20 minutes from Bainbridge. Originally built in 1908, the building features 2 stunning lofts, Bricks & Brass! This unit, "Brass" features 1500 square feet of 12 foot ceilings, heart pine floors, and original brick walls. Stylishly decorated to add the modern conveniences of today! Things to note! To access the unit, you'll have to walk upstairs and entrance is off of Main Street

4.86 out of 5 average rating, 29 reviews

Top guest favorite

A spacious living area features a large sectional sofa positioned around a cozy fireplace with a brick surround. Wall art adorns the walls, and a round mirror and plant accentuate the room. Natural light enters through the nearby doorway, complementing the warm atmosphere.

Home in Tallahassee

Hummingbird Haus | 2 Unit | 9 Beds | 6 BR | 3.5 BA

Welcome to Hummingbird Haus, a charming 3200 sqft, 6-bedroom, 3.5-bath home featuring 2 expansive decks— one of which incorporates a large tree, creating a cozy, treehouse-like atmosphere. This elevated home is situated on a cul-de-sac in a scenic neighborhood, close to FSU and Downtown. Enjoy being close to it all while having a peaceful retreat to unwind. The layout includes a spacious 4-bedroom, 2.5-bath main home on the upper level, along with a 2-bedroom, 1-bath suite on the lower level.

4.98 out of 5 average rating, 160 reviews

Top guest favorite

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.

Guesthouse in Tallahassee

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.

4.87 out of 5 average rating, 390 reviews

Top guest favorite

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.

5.0 out of 5 average rating, 24 reviews

Top guest favorite

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.

4.94 out of 5 average rating, 106 reviews

Top guest favorite

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.

4.97 out of 5 average rating, 328 reviews

Guest favorite

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.

Home in Tallahassee

Mi Casa Su Casa

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!

4.85 out of 5 average rating, 554 reviews

Guest favorite

Home in Tallahassee

Smart Home Near FSU, Big Backyard, Family Friendly

Modern 4BR smart home in Tallahassee, minutes from Florida State University (FSU), FAMU, and downtown. Ideal for game-day weekends, graduations, family visits, and group getaways. Minimalist modern interior with 4 bedrooms, 3.5 baths, and a spacious lanai with patio lounge chairs. Large fenced backyard surrounded by lush greenery, perfect for kids, pets, and outdoor gatherings. BBQ grill and outdoor dining available. Free parking and smart home features throughout.

4.92 out of 5 average rating, 119 reviews

Superhost

Home in Tallahassee

Designer Lakefront 12 Min to FSU

Discover your private lakefront retreat on Lake Bradford, Tallahassee, perfect for up to 6 guests. This unique property offers direct lake access, a private sandy beach, and stunning water views. Enjoy a fully equipped kitchen, cozy fireplace, and outdoor grilling area. Conveniently located near FSU, FAMU, and downtown, a 5 minute drive to the TLH Airport. It's your serene escape with modern comforts and easy access to local attractions.

5.0 out of 5 average rating, 3 reviews

Top guest favorite

A peaceful lake scene is presented, featuring a soft sunset reflecting on the water's surface. A wooden dock extends into the lake, surrounded by lush trees. The horizon is marked by silhouettes of distant land, creating a serene ambiance.

Home in Quincy

Stunning sunrises await at your Talquin lake house

This 4 bedroom, 2 bath lake house boasts over 2,000 square feet of room for you to relax and enjoy. The quiet neighborhood allows you to connect with nature in a peaceful setting. Plenty of room outside for fishing or relaxing. Roomy inside with all the comforts you are used to - including DirectTV, wi-fi, gas fireplace, and more. Minutes from historic Quincy, Florida and interstate access for quick trips to Tallahassee.

5.0 out of 5 average rating, 32 reviews

Superhost

Home in Havana

The Cottages, Unit 1

Discover a delightful getaway surrounded by nature at The Cottages, Unit 1. This cozy two-bedroom haven is perfect for couples or small families seeking a peaceful getaway. With its serene surroundings and modern amenities, you'll find everything you need for a relaxing stay. Located 20 minutes from Tallahassee, 20 minutes from Bainbridge, GA and 45 minutes from Thomasville, GA.

5.0 out of 5 average rating, 3 reviews

Top guest favorite

The exterior of a modern single-story home is displayed, featuring a stone facade and a light-colored roof. A spacious driveway leads to a two-car garage. Well-maintained landscaping includes a grassy area and decorative plants near the front entrance, enhancing the welcoming appearance.

Home in Tallahassee

Private Spacious New 4 Bdrm W/ Whirlpool Tub

Forget your worries in this spacious and serene space. Perfect for families. Located in on the Northwest end of Tallahassee. This quiet gem is a brand new construction! This home boast a large open concept living room and kitchen area, 4 spacious bedrooms, back patio, and all the comforts of home. We look forward to sharing our space with you!

5.0 out of 5 average rating, 53 reviews