House holiday rentals in Lakeland

4.96 out of 5 average rating, 141 reviews

Home in Lakeshore

Clean Lakeland Home w/ Water Views & RV Parking!!!

This super clean, cute as a button Single Family Home provides ample parking with a huge fenced in backyard perfect for your short-term stay! You will find thoughtful touches throughout like USB Wall Outlets and complimentary bicycles! Conveniently located at the center of Lakeland, just minutes of a walk to Lakeland Regional Medical Center (Hospital) along with the newly constructed Carol Jenkins Women's Center. This home has it all and anxiously awaits your arrival to begin making memories!

Superhost

4.86 out of 5 average rating, 123 reviews

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.

Home in Lake Hollingsworth

4.98 out of 5 average rating, 138 reviews

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, smart TVs and WiFi throughout, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

4.99 out of 5 average rating, 138 reviews

Home in Winter Haven

Beautiful Lake House Boating Fishing near Legoland

Welcome to The Executive Lake House ten minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers two bedrooms, a , full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is ( not) included at this price point. If wanting an additional charge of 20 dollars per night Will be charged. Let me know at booking.

Superhost

Home in Dixieland

4.83 out of 5 average rating, 174 reviews

Hollingsworth Pool Home

This artistic, craftsman-style pool home is regally situated on a red brick street in Lakeland's beloved Lake Morton Historic District. Centrally located, with Lake Hollingsworth just 2 blocks away, the Hollingsworth House is also walking distance to Cob & Pen, Concord Coffee, and the trendy Dixieland neighborhood where you can shop at antique and boutique shops. The large pool is surrounded by 8 foot privacy fence and a fully-fenced in backyard. Free driveway parking.

Home in South Lake Morton Historic District

4.93 out of 5 average rating, 100 reviews

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.

4.97 out of 5 average rating, 105 reviews

“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.

Home in South Lake Morton Historic District

4.88 out of 5 average rating, 163 reviews

The Funky Swan Shack by Lake Morton & Downtown

Enjoy every pop of color in our Vintage Florida Cottage located in the Lake Morton Historic District and just a short walk to Lake Morton, Lake Hollingsworth, and Florida Southern College. This home is just one mile from Downtown Lakeland, Dixieland Historic District, and all of Lakeland’s top restaurants and bars; and is in an absolutely perfect location for exploring all of Lakeland, Tampa, Orlando, Disney World, and Florida beaches.

4.89 out of 5 average rating, 112 reviews

Magnolia Manor | Bungalow Near Downtown Lakeland

Welcome to our cozy and comfortable home that is the perfect place for visiting Lakeland. The house features 3 bedrooms, 2 bathrooms, and can comfortably accommodate up to 8 guests. It has a fully equipped kitchen, a living room, dedicated work space for remote workers, and a dining area, perfect for gatherings. The house is located just minutes away from downtown, where you'll find a variety of restaurants, shops, and parks.

Superhost

4.8 out of 5 average rating, 100 reviews

Heart of South Lakeland in adorable neighborhood!

In the heart of South Lakeland, in one of the most sought out locations. Easy access to a variety of restaurants, shopping and minutes away from the Polk Parkway and South Florida Ave. Whether your destination is here in Lakeland, to the beach, or off to see Mickey, our goal is to make you feel at home! The home features a newly remodeled kitchen, a smart tv, memory foam mattresses, and all the coffee!

4.95 out of 5 average rating, 145 reviews

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.