Holiday rentals in Lake Hollingsworth

Private 2BR Home Near Tigertown • Pet Friendly

Experience comfort and privacy in this fully renovated 2BR private home near Tigertown. Designed for professionals and extended stays, it features a workspace, fast WiFi, Smart TV, in-home laundry, and relaxing front porch. Located in a quiet, safe neighborhood minutes from downtown, hospitals, dining, and shopping. Pet friendly (yard not fenced). Ideal for longer, comfortable stays. LegoLand 25 mins Bush Gardens: 45 mins Disney World: 45 mins Downtown Restaurants: 3-10 mins Mall/Cinema: 8 mins

Sunshine Studio + Courtyard, Firepit, near downtwn

Your cozy retreat awaits you in Sunshine Studio! It is centrally located in Lakeland, a short drive from downtown, Florida Southern College (1.4 miles) Southeastern University (1 mile) The studio comes fully equipped with everything you need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the well appointed modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Private parking is just a few steps down the pathway through the courtyard from your door!

University District Historic Bungalow

Escape to our home, perfectly situated in the heart of the most exclusive & upscale neighborhood downtown Lakeland! This safe, serene enclave offers the best of both worlds: a peaceful spotless retreat just steps from the area’s most popular Lake Hollingsworth, renowned FSU & SEU. Stroll to the vibrant lakefront for scenic walks, and drive 10 mins to the famous Florida Joker Stadium and enjoy the games & everything Tigers Spring Training! 1/2 way between Orlando & Tampa! Book your stay today!

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!

1/1 Affordable Downtown Pet Friendly Home

This charming second-floor home is perfect for you, your family, and your pets to enjoy! Nestled in the safe & historic neighborhood of Dixieland, we proudly welcome pets for a comfortable stay. Message us with any questions. What's near? Lakeland's historic parks, beautiful lakes, famous bakeries, wine bars, live music, & restaurants. St Pete Beach: 1 hr Disney World: 40 min Tampa: 38 min Lego Land: 30 min Mall/Cinema: 13 min Please reach out with any questions or booking inquiries.

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!

Life in a Shipping Container!

Peace and quiet on a small country farmstead. Off the beaten path yet conveniently located halfway between Disney World and Clearwater Beach. Historic Plant City, famous for their strawberry farms, has a cute downtown area with antique shops, bistros and cafes. Relax on your private back deck overlooking our organic vegetable garden. Say good morning to a variety of birds (including welcoming our newest chicks) living on the property and goats, cows and horses living nearby.

Central Location, Charming Historic Bungalow

Craftsman style bungalow on quiet, cobblestone streets in a beautiful Historic District. Enjoy the neighborhood park, sip a latte at the Hillcrest Coffee Shop, enjoy the birds and wildlife of Lake Hunter or take a short walk to downtown Lakeland with it's many wonderful restaurants, entertainment venues and more beautiful lakes. The RP Funding Center is a 10 minute walk away and the location also provides easy access to I-4 for trips to Tampa or Orlando.

“Our Nest” Cozy Retreat Near Downtown & FSC 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.

Retro 70s Style Downtown LKLD, Florida Southern

Step back in time at this 70’s-style retro retreat in Downtown Lakeland! Perfectly located and within walking distance of Florida Southern College and Lake Morton, and just minutes from Lake Hollingsworth and our vibrant Downtown. This one-bedroom gem features a queen bed, one bath, a cozy living room with a queen sleeper sofa, a fully stocked small kitchen, and a charming coffee bar. Enjoy a stylish and comfortable stay in the heart of it all!

*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.