Vacation rentals in Lakeland-Winter Haven Metropolitan Area

Historic Downtown Bungalow w/piano

NO PET OR CLEANING FEES. The Daugherty House, a refurbished, downtown Lakeland, 1918 historic, 3 bed, 2 bath bungalow, between Lake Mirror and Lake Morton, features a 1907 upright piano, beautiful bedrooms with new mattresses and box springs, a spacious rocking chair front porch, cozy Florida room with a fold out couch, a gas fireplace, and memorabilia from Lakeland's history. The home's filled with antiques and modern conveniences, and the kitchen has all your cooking needs. CLICK SHOW MORE.

The Woodsy Weekender

Take it easy at this unique and tranquil getaway in the woods. Wake up in one of our cozy queen or full sized beds, and enjoy coffee and hot chocolate on the 2nd story deck. 10 minutes from downtown Lakeland, spend your day walking our beautiful lakes and eating at our foodie hotspots. End your day back the at Woodsy Weekender making dinner in our full kitchen and sipping wine on the screened in back porch swings watching the sunset. The perfect little "Safe Haven" cabin for all occasions.

Matty’s Citrus Connection

You are going to love this Citrus themed hideaway with its Old Florida feel that takes you back to simpler times. Rest and relax in this backyard paradise while enjoying all that Lakeland has to offer. Whether you choose a relaxing day enjoying the many local activities , take a day trip to a beautiful Florida-beach , or decide to visit one of Florida’s theme parks , this is the place to stay . We are centrally located and have quick access to Polk Pkwy , so your adventures are unlimited .

Romantic Lakefront – Feed Swans – Walkable Dining

Discover SWAN LAKE VACATIONS. Swan elegance meets city charm steps away. Highlights: • Lake Views • Downtown Stroll • King-sized bed • Modern Comfort • Full Kitchen • Semiprivate Patio • Between Tampa & Orlando Why Swan Lake Vacations? • Central Hub • Safety Assurance • Easy drive to beaches and Walt Disney World • Experienced Hosts Escape to Swan Lake Vacations—a place where swans grace the surroundings next to quaint downtown life. Book for a perfect blend of nature and urban comfort!

Gorgeous Gem in the Heart of Lakeland

LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

Studio apt in Historic area of Lakeland

This second story studio is on our homes property. It has a Queen bed, bathroom and kitchen. It is nestled in the historic area of Lakeland, one block in from The "Frank Lloyd Wright" designed Florida Southern college, tours are available! Our Cobblestone streets take you to our neighborhood restaurants, the art museum, library, Hollis garden, we are between two lakes-Hollingsworth it has a great walking/running path, and Lake Morton a bird paradise. All within walking distance.

Charming Historic Area Retreat!

Welcome to our charming one-bedroom short-term rental nestled in the scenic Lake Morton Historic District and conveniently located near the prestigious Florida Southern College. This thoughtfully designed accommodation offers a perfect blend of modern comfort and historic charm. Situated just a stone's throw away from the beautiful Lake Hollingsworth and Lake Morton our property provides an easy access to leisurely strolls around the lake and jogging trails.

Our Nest | King Bed | Frank Lloyd Wright Campus

Welcome to Our Nest—a peaceful retreat along Lakeland’s historic brick streets. Just steps from Frank Lloyd Wright’s iconic architecture, this one-bedroom stay offers a plush king bed, stocked kitchen, fast Wi-Fi, smart TV, and a private patio perfect for slow mornings or quiet evenings. Walk to Lakes Morton and Hollingsworth, explore cafés, or relax as swans drift by. Clean, quiet, and thoughtfully prepared—the kind of place we’d want to find ourselves in.

La Casita Azul

The Little Blue House is a studio,guest house in our backyard. Separate entrance on the opposite side of the main house. This cozy comfortable room has a microwave, small refrigerator/freezer, and Kurig coffee maker( coffee included).It is perfectly located in the historic East Lake Morton, walking distance to Lake Morton, Lake Mirror, and downtown Lakeland. Perfect location to enjoy Lakeland.

Charming Lakefront Cottage with Stunning Views

Welcome to our lake house retreat in Lakeland, Florida. You can enjoy a peaceful getaway with beautiful sunset views and tranquil waters during the evenings, and still visit major cities such as Orlando and Tampa during the day which are less than an hour away. Minutes from Southeastern University, Florida Southern, Lake Hollingsworth, and other attractions in the Lakeland area.

*Modern* Guesthouse steps to Lake Hollingsworth

This 1-Bedroom Guesthouse is located just steps away from Lake Hollingsworth. Enjoy all the activities, restaurants, and bars in downtown Lakeland. Tastefully renovated, this guesthouse was designed to provide comfort and a easy commute to Florida Southern College, downtown Lakeland, Lake Morton, Lake Mirror, and Dixieland Historic District.

Cottage in Lakeland w/ Parking

Spacious Cottage/Guest House, centrally located in Lakeland downtown. There is a beautiful park across the street for exercising. Walgreens one block away, local bars, restaurants, antique stores and lots of lovely historic bungalows. This unit has the access through the alley. It is easy to find, very private and peaceful