Vacation rentals in Lake Hollingsworth

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.

Swan City Studio +Courtyard, mins historic 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) SEU(1 mile) 17 mins from SUN N FUN!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!

Lakeland LakeFront 4BD | 3BA FSC SEU Sun & Fun Tigers

Welcome to Laketitude—your spacious lakefront escape on Lake Hollingsworth! Just steps from Florida Southern College and Frank Lloyd Wright gems, minutes to downtown Lakeland, Sun ’n Fun, and Tiger Town, with Tampa and Orlando only 40 mins away. This 4BR/3BA retreat sleeps 10 and features a large backyard, 65” Smart TV, Xbox, coffee bar, and full kitchen—perfect for families, college visits, and getaways. Don’t miss out on our deep connection with FSC’s rich history- message us to learn more!

Luxury 3BR Near Downtown | Pet Friendly + Peaceful

Welcome to your Lakeland retreat! This charming 3-bedroom home is thoughtfully styled, exceptionally clean, and fully equipped with all the conveniences of home. Located in the peaceful Lake Hunter neighborhood—just minutes from downtown, colleges, and spring training—it’s perfect for families, couples, or business travelers. Relax inside or enjoy the private backyard patio. Pets stay free! 8 mins to FSC 10 mins to Detroit Tigers 13 mins to Sun ’n Fun 30–45 min to Legoland, Disney & Tampa

Top 1% Stay – Cozy Lakefront with Hand-Fed Swans

In the Heart of Lakeland, FL... on the Banks of Lake Morton! Nestled between the Historic District and beautiful South Lake Morton Historic District... (or as we like to call it, "Swan Lake") this property is located in easy walking distance to: Restaurants & Shopping Lakeland Public Library The Polk Museum of Art Historic Downtown Lakeland Lake Hollingsworth Florida Southern College Lake Mirror Hollis Gardens AND of course... Lake Morton Take it easy at this unique and tranquil getaway.

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!

King Beds+Pet Friendly | Near Downtown & Tigertown

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

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.

Charming Bungalow with Front Porch

Enjoy peace and serenity at this centrally located, charming, 1920's bungalow in Lakeland. You will find the front porch an inviting spot to relax and unwind on this quiet street in the Lake Morton historical district. Downtown Lakeland, a Publix grocery store, Dixieland shopping, restaurants, bars and a liquor store are less than a five minute drive away. FSC, Lake Morton and Lake Hollingsworth with its 3 mile, paved walking trail are within a few, walkable blocks.

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.

*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.