Vacation rentals in Havana

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.

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.

Cozy Country Cottage - Waterfront!

Enjoy the sounds of nature when you stay in this unique country cottage on private Turkey Pond. Deer, turkey & raptors are just some of the wildlife you may encounter. Stunning sunsets are common & kayaks are on hand for a paddle. There is outdoor seating & a sun umbrella for the porch and stars twinkle on clear nights. Special touches make your stay comfy & cozy including on-demand hot water, a luxurious queen bed w/ a cozy comforter, mini-split heat/ac, dish network, smart tv & much more.

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.

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!

Shangri-La Treehouse

Shangri-La Treehouse is the 1st and only luxury treehouse in Tallahassee, Florida's Capital City. Nestled between ancient oaks, Shangri-La Treehouse is luxury in the wild where serenity is found. You are invited to enjoy 9.5 acres of verdant land amidst ducks, deer, owls, and other assorted wildlife that call Shangri-La home. A thoughtful, adults only (21+) romantic getaway for 2 that can accommodate up to 4 guests comfortably.

Cottage in the Woods

Newly listed in August 2025! Enjoy a private getaway in our 1,100 sq. ft. guest house, tucked at the back of a 3.5-acre wooded lot with your own driveway and entrance. Just minutes from Maclay Gardens, Lake Overstreet Trail, and Elinor Klapp-Phipps Park, it’s perfect for outdoor lovers who also want a peaceful place to unwind after a day at the Capitol or a big game at FSU. The house can accommodate up to two guests.

Historic Havana's Horseshoe Bungalow!

Stay in the heart of downtown Havana at the Horseshoe Bungalow, a renovated 3BR/2BA home with modern style and cozy charm. Enjoy a full kitchen, inviting living room, and updated baths. Sleeps up to 6 with comfortable beds and luxury linens. Outside features include a private carport with an EV outlet, perfect for charging your electric vehicle. Walk to shops and cafés or relax in your own stylish retreat.

The Cottages, Unit 2

Discover a delightful getaway surrounded by nature at The Cottages, Unit 2. This cozy two-bedroom, one-bathroom 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.

Gardenview Tiny House

Enjoy the sounds of nature when you stay in this unique tiny home in a garden setting. Quiet and private neighborhood. Our Tiny House space is perfect for one guest. We are located about 8 miles (15 to 20 minutes by car) from the Forida Capitol Building and the FSU Campus. We offer a 15% discount for bookings of 7 days or more, and 40% discount for 28 days or more.