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.

Location · Family · Parks

Downtown Lkld-Urban Luxury Loft

Discover urban comfort in our Downtown Lakeland Studio Loft! This trendy third floor apartment accommodates 4 guests, boasting open industrial ceilings and historic brick walls that add a chic touch to the space. The floor to ceiling windows bring in gorgeous natural sunlight. Step outside and immerse yourself in the heart of the city, with cafes, shops, and attractions just a stroll away. Whether you're here for business or leisure, our loft offers the perfect blend of style and convenience!

Family · Location · Parks

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.

Location · Value · Kitchen

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 .

Value · Location · Kitchen

Private Bungalow In Peaceful Downtown Lakeland

Unwind in our Serene downtown Lakeland! This peaceful home perfect for families and groups. ★ "Very pretty house and clean! And the host was always responsive. Would definitely stay here next time!!" This bungalow in close proximity to the best attractions and lifestyle Florida has to offer. This home has many restaurants and shops located nearby to choose from. The perfect place to relax and enjoy the historic city of Lakeland. A quick walk to Lake Hollingsworth and or nearby museums.

Family · Value · Decor

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!

Family · Value · Condition

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.

Location · Value · Hospitality

Eclectic On The Alley

1925 Historic Downstairs Garage Apartment in the highly desired Dixieland District, that has antiquing, restaurants, bakeries, coffee shops, and more...all within walking distance! Within a block from either side of the house is Reececliffe Diner and Patio 850, that's a restaurant and wine bar. It’s a lovely five minute walk to Lake Morton, home of the swans, from which our nickname “Swan City” hails. You can easily walk to downtown, which is a total of one mile from the house.

Location · Family · Sleep quality

Luxury near Downtown Lakeland | Walk to the Lakes

Welcome to The Laureate House, a thoughtfully restored century-old home where historic charm meets soft luxury. With 2 king bedrooms, 2 baths, and a bonus bedroom, the home sleeps 7 comfortably. Original hardwood floors, elegant details and warm natural light set a timeless tone, while modern updates ensure comfort and relaxing peace. Located on one of Lakeland’s most sought-after streets between Lake Morton & Lake Hollingsworth, just minutes from downtown.

Location · Value · Sleep quality

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.

Family · Value · Nearby

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.

Location · Family · Access

Lakefront 3BR/2BA near downtown Lakeland

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.

Value · Location · Walkability