Vacation rentals in Havana

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.

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!

Magnolia Barn | 9+ Beds | 7+ BR | 3 BA | 10+ Cars

Conveniently located on High Rd, just down the street from FSU’s Doak Campbell Stadium, this renovated 7+ bedroom home is ideal for visitors to Tallahassee. Nestled on 2 acres in the heart of the city, this spacious residence boasts 3,700 sqft of charm and comfort. This home is designed to meet the needs of any large group. Please note, this listing includes 7 of the 8 bedrooms. If you're interested in the additional 400 sqft King bedroom on the rear first floor, please reach out for rates.

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.

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.

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.

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!

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.

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.

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.

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!

Pristine Elegance meets Chic Charm

Live like a local with this property, just a few miles from FSU and FAMU, where you're close to everything happening in town. Super convenient. Family-friendly. Fully fenced back yard. Amenities include high-speed Wi-Fi, toiletries, coffee, and smart TVs. All our furniture is brand new, with a full-functioning kitchen and laundry room.