Holiday rentals in Havana

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.

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!

Walk to Museum | Near FSU | EVSE

* Lake Water severely is low, Tallahassee is in a drought* ✈️ 5 minutes from Tallahassee Airport! 🏟️ 12 minutes from Capitol, FSU, FAMU and TCC 🤪 No crazy check out instructions! 🐕 Pet friendly! 🛶 Kayaks available! 🔋Remote control bed! 🌺Nature trails! ⛵️Private Lake access! 👩‍💻Traveling work friendly! 🎣Fish off the dock! 🔑 Remote and keyless entry. ⛳️ Golf course 10 minutes away! 🚿 Walk in shower and separate tub! 🎸 Piano, guitar, and board games available 🍳Awesome Grill set up!

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.

Luxe Downtown Modern

Step into elegance as you enter this beautifully designed residence, featuring high ceilings, modern furnishings, and tons of natural light. Sleeps 10 - Master:king-sized bed, en-suite bathroom with walk-in shower - Room 1: 2 queen-sized beds - Room 2: 2 queen size beds - Wi-Fi - Smart TVs all rooms - Washer and dryer - Electric fireplace 4.9 miles to FSU campus 5.1 miles to FAMU campus. This house shares the property with a cottage which is also available for rent and sleeps 4

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.

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.