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Holiday houses in Highland City

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Highland City

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of a spacious house is displayed, surrounded by lush green grass and mature trees. A pathway leads to the entrance, flanked by shrubbery. Bright daylight emphasizes the clean lines of the house and the inviting front porch.
Home in Lakeland
4.98 out of 5 average rating, 46 reviews

Tranquility! Cozy and quiet home

Spacious house on a quiet street where you can relax and recharge during your central Florida vacation. Sleeps up to 7 people. Guests have access to a full kitchen, a dining room, a large living room and a patio. Guests can also park up to two cars in the enclosed garage and do laundry in the laundry room. Master bedroom has a king size bed, an en-suite bathroom and a walk-in closet for anything you need to store. bedroom two has a king size bed. bedroom three has one queen and one double bed.

Top Guest favourite
Home in Lakeland
5.0 out of 5 average rating, 49 reviews

Family Heated Pool Home Sleep 12 Near Tampa Disney

Wake up to sunshine, step outside to your PRIVATE HEATED POOL, and let the day unfold at your own pace. This is where FAMILY MEMORIES ARE MADE: kids laughing in the playground, slow mornings with coffee poolside, and evenings enjoying movie nights on the 75” TV. Tucked in one of Lakeland’s most peaceful neighborhoods, this spacious retreat is designed for connection and comfort. About 1 hour from Tampa or Disney, Publix minutes away, quick access to SEU, Florida Southern College, and Polk State.

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

Top Guest favourite
Home in Lakeland
5.0 out of 5 average rating, 42 reviews

Spacious 4BR Pool Home-Guest Favorite

Modern 4BR home in a quiet South Lakeland neighborhood, close to Publix, Sam’s Club, and Walgreens. Walk to Banana Lake or explore Circle B Bar Reserve, just 10 minutes away. Enjoy our nearby lakes, trails and parks. Conveniently located between Orlando and Tampa/St. Pete, making it easy to visit Disney/Sea World/Busch Gardens/Legoland/Spring Training, Gulf Coast beaches, and Central Florida attractions. The perfect home base for work, vacation, graduations or visiting family and friends.

Top Guest favourite
Home in Lakeland
4.97 out of 5 average rating, 35 reviews

“Relaxing Pool Retreat Near Downtown Lakeland”

Bienvenidos a esta hermosa y espaciosa casa ubicada cerca del Downtown de Lakeland a pocos minutos de Lake Hollingsworth .Cerca de Hollis Garden junto a Munn Park ,Bonnet Spring Park .Cerca de Polk Theatre ,Legoland a 25min ,Aeropuerto de Tampa a 45 min ,Parques tematicos de Orlando a 1 hora .A poca distancia de la 92 W ,98 Nt y la I 4 Cocina completamente equipada ,piscina ,terraza techada y gran jardin asegurado y completamente cercado para la seguridad de sus mascotas y niños

Guest favourite
Home in Lakeland Highlands
4.88 out of 5 average rating, 40 reviews

Private Pool + Arcade | Near Hospitals & Downtown

Spacious 4BR Lakeland home with private pool, arcade game room, free parking, king & queen beds, fast Wi-Fi, workspace, full kitchen, and roomy living areas. Near Christina Park, Elite Fall Classic Volleyball Center, Advent Health Field House, ISPS August Heat – Softball, Lake Myrtle Sports Park, Lakeland Square Mall, Downtown Lakeland, Lakeland Linder Airport, Orlando Health Lakeland Highlands Hospital, Watson Clinic, Bonnet Springs Park, First Friday events, and LEGOLAND Florida.

Guest favourite
Home in Lakeland
4.89 out of 5 average rating, 18 reviews

Cozy 3BR Home |Pet-Friendly |Near Legoland & Tampa

Welcome to your perfect Lakeland getaway — where comfort meets convenience in the heart of Central Florida. This beautifully updated 3-bedroom home is ideally located just minutes from Downtown Lakeland, Lake Mirror, Florida Southern College, SUN ’n FUN, and Legoland Florida — making it the perfect home base for families, couples, and business travelers alike. Enjoy a peaceful neighborhood setting while staying close to everything. Quick access to Tampa & Orlando attractions

Superhost
Home in Lakeland
5.0 out of 5 average rating, 3 reviews

Conveniently Located Pool Home Pet/Family Friendly

Discover comfort & convenience in this charming home featuring open-concept living spaces perfect for relaxing or entertaining. The spacious primary suite offers a peaceful retreat, while the sparkling pool and fenced backyard create an ideal outdoor oasis. Pet friendly, located in a quiet neighborhood close to shopping, dining, and local attractions, this home is perfect for families, couples, or extended stays. Located less than 5 mins from the new Orlando Health Hospital!

Guest favourite
An inviting swimming pool is surrounded by a spacious patio area, featuring lounge chairs and a shaded table with an umbrella. The serene view of Little Lake Otis and lush greenery is visible in the background under a partly cloudy sky.
Home in Winter Haven
4.91 out of 5 average rating, 222 reviews

Legoland Lakehouse Canoe&Kayak Retreat

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

Guest favourite
The saltwater heated pool is enclosed within a screen patio, surrounded by a well-maintained white fence. Comfortable cushioned seating is visible nearby, along with potted plants adding a touch of greenery. Clear blue skies enhance the peaceful atmosphere of the outdoor space.
Home in Lakeland
4.85 out of 5 average rating, 40 reviews

Relax in Heated Saltwater Pool w/ Screened Lanai

Experience luxury and comfort in this spacious rental featuring a master suite with king bed and en suite bath, fully equipped kitchen, dedicated office, and cozy living areas. Enjoy a heated saltwater pool, outdoor TV, grill, and large fenced yard. All bedrooms have large beds, TVs, and ample storage. Includes free WiFi, private driveway, and welcome snacks. Perfect for families, couples, or business travelers!

Top Guest favourite
A spacious bedroom features a large bed dressed in soft pink bedding, complemented by decorative pillows. A bedside table holds a modern lamp, and a full-length mirror reflects the soft ambiance. A wall-mounted television is visible, enhancing the room's functionality.
Guesthouse in Lakeland
4.99 out of 5 average rating, 100 reviews

Estancia íntima y Serena

Descansa en esta estancia íntima y serena, perfecta para dos huéspedes. Cuenta con un dormitorio con cama king, baño completo y cocina equipada. El diseño blanco transmite calma y frescura. Disfruta del patio privado con columpio y mesa al aire libre. Comienza el día con café bajo el cielo o relájate por la tarde en el columpio. Ideal para parejas o viajeros solitarios que buscan privacidad y tranquilidad.

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, 132 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!

Popular amenities for Highland City holiday rentals