Holiday houses in Lakeland-Winter Haven Metropolitan Area

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Top-rated holiday rentals in Lakeland-Winter Haven Metropolitan Area

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Guest favourite
A small outdoor seating area is presented with a black round table and two folding chairs, situated on a green lawn area. A door adorned with a floral wreath provides access to the suite. Surrounding plants add greenery to the tranquil space.
Guest suite in Lakeland
4.86 out of 5 average rating, 164 reviews

Private Studio Suite

🧳 Perfect for a solo traveler or couple looking to visit the peaceful city of Lakeland. 📍Located about 40 minutes from Tampa and an hour from Orlando, in the family friendly area of Lakeland Highlands. - There’s nearby trails, grocery stores, convenience stores and eateries. - Polk Parkway is less then 10 minutes away, it’s the quickest route to get to i4. 🏠 The suite includes a private entrance with full bathroom and backyard area. 🚗 Free Parking Space(s) 👐🏽 Flexible & Contactless Entry

Top Guest favourite
The Tiny House is situated in a serene outdoor setting, featuring a light-blue exterior with a metal roof. A wooden porch with rocking chairs extends at the front, while the surrounding landscape includes lush green grass and landscaping along a gravel path.
Tiny home in Lakeland
4.99 out of 5 average rating, 116 reviews

Charming Tiny House on 5 acres with POOL/ HOT TUB

Escape to the heart of Lakeland where our charming Tiny House awaits. Nestled on 5 acres of tranquility, you'll experience the best of both worlds: a peaceful retreat and easy access to local shopping centers just a stone's throw away. The Tiny House is furnished with a queen size bed and a king sized bed in the upstairs loft, kitchen, full bath as well as a designated work area. Take a refreshing dip in the shared pool, unwind in the hot tub, or simply soak up some sun on the lounge chairs.

Guest favourite
A quaint green cabin is nestled among tall trees, featuring a sloping roof and large windows that invite natural light. String lights are visible, adding a touch of charm, while the front porch offers a welcoming space for relaxation.
Home in Lakeland
4.87 out of 5 average rating, 128 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.

Top Guest favourite
A bright workspace is featured, highlighted by large windows allowing natural light to fill the room. A simple desk is paired with a chair, and a vibrant plant adds a touch of greenery. The tranquil view of Lake Morton is visible through the windows.
Apartment in Lakeland
5 out of 5 average rating, 143 reviews

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.

Top Guest favourite
The open living area features a comfortable sofa set, a stylish area rug, and large windows allowing natural light to fill the space. An island kitchen with contemporary bar seating and modern appliances is visible, creating a seamless flow between dining and living spaces.
Home in Lakeland
4.98 out of 5 average rating, 143 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!

Top Guest favourite
A two-story green studio building is prominently displayed, featuring white accents and large windows. A set of stairs leads to the entrance. The surrounding area is landscaped with small plants and a paved path, offering a welcoming and tidy exterior.
Guesthouse in Lakeland
4.89 out of 5 average rating, 124 reviews

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.

Top Guest favourite
A spacious bedroom is furnished with a large bed, accompanied by bedside lamps. A cozy chair and a vibrant yellow sofa provide seating options. A dining table for two is positioned near the window, while framed artwork decorates the walls.
Home in Lakeland
4.93 out of 5 average rating, 107 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.

Top Guest favourite
A craftsman style bungalow is depicted, featuring a blue exterior and a welcoming front porch with white railings. Lush greenery surrounds the house, complemented by colorful flowering plants. The structure is set under a bright sky, framed by large trees providing shade and a sense of tranquility.
Bungalow in Lakeland
4.95 out of 5 average rating, 111 reviews

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.

Top Guest favourite
The quaint lakefront cottage is framed by large, leafy trees and draped with Spanish moss. A gravel entrance leads to a welcoming porch, featuring large screened windows. Lush greenery surrounds the property, creating a natural, serene setting.
Guesthouse in Lakeland
4.98 out of 5 average rating, 253 reviews

Modern lakeside retreat by SEU and FSC

This 1/1 lakefront historic cottage, built in 1920, is separate from the main house with its own entrance, parking, front porch & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks and fishing poles are provided for your enjoyment during your stay. Come unwind and enjoy the lake views from the hammock and private beach!

Guest favourite
A spacious outdoor area includes a pool surrounded by a white deck. Seating options are available, featuring lounge chairs and tables. The two-story building provides multiple balconies, framed by lush greenery and palm trees, contributing to a serene environment.
Loft in Auburndale
4.93 out of 5 average rating, 228 reviews

2 Bedroom Apartment near Legoland and Disney

This Private Studio features 2 bedrooms, kitchenette with dining area, private bath, walk-in closet, own entrance and from the Main Studio bedroom a large Balcony with Spectacular lake views. The Kitchenette with dining table and the bathroom is located in between of the 2 Bedrooms. The second Bedroom is only 10'x10' with a Queen bed and Wardrobe. Early Check in or late check outs are not available

Top Guest favourite
The image captures a serene lake view from a grassy area, with a wooden deck overlooking calm waters. Lush trees frame the scene, providing shade and a natural ambiance. Water lilies are visible on the surface, enhancing the tranquil lakeside setting.
Home in Lakeland
4.94 out of 5 average rating, 153 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.

Guest favourite
A living area features a blue sofa adorned with decorative pillows, a wooden coffee table, and a cozy armchair. A wall-mounted television is positioned above a white fireplace. Natural light filters through a window with sheer curtains, while a wooden table stands against the wall.
Apartment in Lakeland
4.89 out of 5 average rating, 208 reviews

Adorable 1 bed/1bath with office and free parking

This beautiful duplex is located in a Historic Bungalow built in the late 1920s, centrally located in Lakeland downtown. Nice park across the street for exercising or spending time with kids. Walgreens is one block away, and local bars, restaurants, antique stores, and lots of beautiful historic bungalows

Popular amenities for Lakeland-Winter Haven Metropolitan Area holiday rentals