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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.

Adult-Only Retreat w/ Pool & Spa | 18+, Private

🔒⛓️🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

LKLD Legacy near Downtown Lakeland

The LKLD Legacy is a midcentury ranch, and third generation owned home, in the heart of Lakeland. It's located 5 minutes from downtown, near colleges, and close to I4 exits toward Tampa & Orlando (37mi to Disney, 19mi to Legoland)! The home is in a family-friendly neighborhood and within walking distance to parks and lakes. The large fenced in backyard is perfect for kids and pets (*pet fee required*). Before you leave, snap a photo with the instant camera and add it to our guest photo album!

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!

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 .

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!

3 Bedroom House | 2 Blocks from Lake Hollingsworth

Enjoy the convenience of this beautiful home located around the most sought-after area, Lake Hollingsworth. Located just two blocks from the lake, one block from Cleveland Heights country club, and directly across from Common Ground park, this property boasts an unbeatable location. Comfortably sleeping 6 guests, this 3 bedroom, 2 bathroom home is the perfect place to stay when visiting Lakeland if you want to experience all of the city's beauty, restaurants, shopping, and things to do.

Kid-friendly Home w/ Pool & BBQ

Enjoy a delightful stay in our Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, washer, Wi-Fi, fully equipped kitchen, baby proofed, and BBQ to make your stay comfortable. Enjoy the private pool, free parking, and large patio. Our house is 20 mins away from LEGOLAND and 50 mins away from Disney Parks and attractions. Discover Winter Haven’s chain of lakes with all the water sports and its surroundings in the best way. We look forward to hosting you!

Modern lakeside retreat by SEU and FSC

This 1920’s 1 bedroom 1 bath lakefront historic cottage is separate from the main house with its own entrance, parking, screened front porch, fire pit dock & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks, stand up paddle board, 4 seater pedal boat, and fishing poles and tackle are provided for your enjoyment. Come unwind and enjoy the lake views from the hammock and private beach!

Legoland Lakehouse Canoe&Kayak Retreat

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

Cozy 2-bedroom guesthouse on the lake

Enjoy a relaxing getaway on the beautiful Lake Ariana. Two bedrooms with queen beds comfortably accommodating four adults. Fully equipped kitchen and full bathroom with tub. Laundry room with washer and dryer. Private parking with plenty of room for boat or jet skis. Private entry with hosts on premises. Camera at exterior door for security. The guesthouse is behind the main home. There is not a view of the lake from inside the guesthouse.

Cozy 3 bedrooms 2 bathrooms

Relax with the whole family at this peaceful and charming home in Winter Haven.This home is centrally located and is within walking distance to Lake Howard , downtown winter haven and plenty attractions We are located 10 minutes from Legoland, Peppa Pig Park, five minutes to Advent Health Fieldhouse, five minutes to Winterhaven Hospital, 45 minutes to Walt Disney World, SeaWorld and Busch Gardens.