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 welcoming living area is adorned with natural wood flooring and a light color palette. A cozy sectional sofa is placed beside a glass-topped coffee table, with decorative elements displayed on a nearby mantle. Decorative plants add a touch of greenery to the space.
Bungalow in Lakeland
4.95 out of 5 average rating, 63 reviews

Historic BoHo Bungalow | Walk to Swan Lake

Conveniently located near the Polk Museum of Art and Lake Morton, this spot offers easy walking access to downtown Lakeland. Lake Morton, known for its beautiful swans and diverse birdlife, provides tranquil strolls and wildlife encounters. The fenced backyard adds privacy, making this area a perfect blend of cultural access and natural beauty. Want to walk to downtown for dinner? Just a 4 minute walk. Check out two restaurants just a minute from your home: Mr. Fish and the new Peach House.

Top Guest favourite
The charming yellow cottage is framed by a white picket fence, featuring a porch with two rocking chairs. The entrance is marked by a light blue door, with windows reflecting a bright and cheerful ambiance. Lush greenery and flowers create a welcoming landscape.
Cottage in Homeland
4.99 out of 5 average rating, 174 reviews

Garden Cottage at The Garden Gate Bed & Breakfast

At the Garden Gate, a fully licensed and professional bed and breakfast, we hope you will find respite; a quiet place to rest, relax and reconnect. The 1905 Garden Cottage, carefully restored and beautifully appointed, will be your home while you are here. Enjoy the view of the cottage garden and its seasonal vegetables and flowers from your front porch rocking chair. Fresh baked cookies and chocolates will greet you upon arrival and you will enjoy a full gourmet breakfast in the morning.

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, 143 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
Guesthouse in Lakeland
4.92 out of 5 average rating, 105 reviews

La Casita Azul

The Little Blue House is a studio,guest house in our backyard. The backyard, which includes a covered deck, comfortable furniture, and a TV, is yours to enjoy. Separate entrance on the opposite side of the main house. This cozy comfortable room has a microwave, small refrigerator/freezer, and Kurig coffee maker( coffee included).It is perfectly located in the historic East Lake Morton, walking distance to Lake Morton, Lake Mirror, and downtown Lakeland. Perfect location to enjoy Lakeland.

Top Guest favourite
A bright workspace is showcased with large windows offering views of the lake. Two yellow armchairs sit beside a glass-top table. A desk with a lamp is positioned against the wall, with a potted plant adding a touch of greenery.
Apartment in Lakeland
5 out of 5 average rating, 122 reviews

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!

Top Guest favourite
A bedroom showcases a leafy green accent wall, complemented by a light wood bed frame. Natural wood flooring adds warmth to the space. The bathroom features a modern vanity with dual sinks and a potted plant, while the outdoor area reveals a pool surrounded by a screened enclosure, illuminated by soft blue lighting.
Guest suite in Lakeland
5 out of 5 average rating, 102 reviews

CasaPlanta Cozy Tropical Guest Suite plantsinrehab

Casa Planta is a garden-inspired oasis where nature & relaxation meet. Our tropical landscape is currently in a seasonal restoration phase due to extreme winter freezes, w/ an evolving garden setting. Recovering plants won't be pruned until April. Enjoy a peaceful walk to your private entrance & unwind poolside in your 2BR/1BA suite. The pool and interior remain exactly as pictured—private, comfy, & serene. The guest suite is attached to the main house but completely blocked off from it.

Top Guest favourite
A single-story house is presented at dusk, featuring a neatly paved driveway illuminated by outdoor lighting. Lush green grass and small landscaping elements frame the home, with a clear sky transitioning to soft shades of orange and pink above.
Home in Lakeland
4.96 out of 5 average rating, 28 reviews

Cozy home conveniently located with fenced in yard

My home is close to restaurants, family-friendly activities, and the Lakeland Linder International Airport. Located minutes from the Polk Parkway for easy travel to Orlando or Tampa. You’ll love this established neighborhood. You will enjoy the spacious 1,320 sq. foot open floor plan, very comfortable house in a great location. My home is great for couples, business travelers, and families. Fully fenced back yard. Please ask if anything is needed and I will try to accommodate.

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
4.96 out of 5 average rating, 115 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.

Guest favourite
Townhouse in Lakeland
4.88 out of 5 average rating, 212 reviews

TRENDY TOWNHOME *Btw beach & Disney+ smart TVs*

The BEST home and BEST service in the state of Florida. Modern, trendy townhome right off highway I-4 between Disney and Gulf Beaches! 3 bed, 2.5 bath townhome. 3 smart Tv’s to make your vacation that much more relaxing. And newly renovated kitchen, stocked with every appliance for short or long term stays. You won't find a better place in lakeland whether you are hosting a couples getaway, traveling for work, or vacationing with your family!

Guest favourite
A spacious living area features a sectional sofa with an ottoman and two accent chairs, set on a soft, light rug. A ceiling fan provides cooling, while natural light filters through a large window dressed with sheer curtains. A small side table with a lamp complements the decor.
Home in Lakeland
4.82 out of 5 average rating, 112 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!

Top Guest favourite
A living area features comfortable leather seating with red accent pillows and a coffee table. A wall-mounted television is positioned across from the seating. Two framed art pieces and green plants add decor to the neutral-colored walls and tiled flooring.
Apartment in Lakeland
4.97 out of 5 average rating, 190 reviews

Your Charming Place in Central Florida

Enjoy this brand new apartment, two bedroom, one bathroom, and full kitchen. Located in north of Lakeland. Easy access to I-4, Orlando, or Tampa. 45mins away from Disney, 40 from Bush Gardens, 35 from Lego-Land, 1hr from Clearwater, and 35 from Ybor City, Tampa. Colleges: 15mins from Florida Southern College and 20mins from both Florida Polytechnic University and Polk State College.

Guest favourite
A spacious sleeping area features a queen bed adorned with neatly arranged towels and decorative pillows. Light-colored bedding contrasts with a soft green accent wall. Nearby, artwork is displayed above the bed, and a cozy sofa and kitchenette are visible in the background.
Guesthouse in Lakeland
4.92 out of 5 average rating, 170 reviews

Cottage in Lakeland w/ Parking

Spacious Cottage/Guest House, centrally located in Lakeland downtown. There is a beautiful park across the street for exercising. Walgreens one block away, local bars, restaurants, antique stores and lots of lovely historic bungalows. This unit has the access through the alley. It is easy to find, very private and peaceful

Popular amenities for Lakeland-Winter Haven Metropolitan Area holiday rentals