Holiday rentals in Havana

D’town Restaurants & Shops & Pool!

King Bed,2.65 acres,Private pool,Dogs OK-$50 non refundable pet fee. 20 min to Tallahassee for sport events, colleges, legislation & business. A taste of Old FL with country breezes & wide open spaces. Stroll to quaint antique shops & eat in our cute cafes. Learn about “The Old Spanish Trail” & the many antique tobacco barns in the area. Cool off in our lovely pool or read under sprawling centuries old Oak trees. End the day at the firepit with a glass of wine or cup of cocoa. Relax & recharge

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.

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.

The Carriage House

Our lovely French inspired guest house features an open floor plan, 12-foot ceilings with real wood beams, a fully equipped kitchen and large brick patio overlooking a spacious backyard with shared pool. The two bedrooms are connected by a jack and jill bathroom featuring a tub/shower combination. the second bathroom, located just down the hall, has a standup shower. For additional guests, there are more sleeping arrangements in the family room on a single bed pullout love seat.

Home away from home Northside charmer suite

Lovely and completely renovated 1100 sqft in-law suite, fully self contained and private. It comes complete with a fully equipped kitchen (no commercial food preparation allowed) and bathroom with walk-in shower. Queen size bed in the bedroom, with a Queen size sleeper sofa in the living room. Has its own private entrances and dedicated driveway parking area, as well as self-check-in. No pets allowed. This is a strict non-smoking space, no smoking is allowed on the property.

Guesthouse - Studio in the woods

Nestled towards the end of a “no thru traffic” street, this adorable studio cottage is on a shared, rural 3-acre property, located down a bumpy dirt driveway back in a wooded setting. 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** (we are in the woods, the ground is uneven and there is a bit of a walk from the car to the entrance).

Rural Estate Near Tallahassee. Sleeps 16

Forget your worries in this spacious and serene Southern Aloha estate, nestled on over 30 acres of peaceful countryside. Perfect for FSU/FAMU visits, intimate gatherings, corporate retreats, or simply unwinding in comfort while exploring Florida’s capital city. Inside, you’ll find multiple cozy living areas, a chef’s kitchen, and a private pool (not heated) with a wrap-around deck. The estate also accommodates small weddings and events for an additional fee.

Sienna Lee Gardens: A Beautifully Renovated Home

Relax and unwind in this beautifully renovated 4 bedroom/3 bath home nestled on 20 acres of picture perfect live oaks, organic blueberry orchard, and abundant wildlife. There are so many places for entertaining including a large heated swimming pool (heated from March-Nov). There's a fully equipped kitchen, luxury beds and hotel quality linens. Every room has cable TV and internet throughout the house.

Cozy Tiny Country Cottage!

Clean, cozy & comfortable! Come enjoy this tiny guest house in the country near the famous Florida Antiques Shopping Trail! A suburb of Tallahassee, just 6 miles North of Lake Jackson, and just 16 miles from Doak Campbell Stadium. Also a relaxing & peaceful traveler’s rest stop - just 14 miles from Interstate 10 exit 199. Be sure to check out my local restaurant Guide Book!