Guesthouse vacation rentals in Lakeland

Find and book unique guesthouse rentals on Airbnb

Quick stats about guesthouse rentals in Lakeland

  • Total vacation rentals

    Explore 50 vacation rentals in Lakeland

  • Nightly prices starting at

    Lakeland vacation rentals start at G$8,371 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,390 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Lakeland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lakeland rentals

  • 4.9 Average rating

    Lakeland stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated guesthouse rentals in Lakeland

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

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Guest favorite
The living area features a dark blue couch adorned with a light throw blanket, positioned on a vibrant orange rug. A sliding barn door is visible, leading to the bedroom. A potted plant adds greenery next to the entrance to the kitchen, showcasing warm wood cabinetry.
Guesthouse in Lakeland
4.84 out of 5 average rating, 139 reviews

Charming Dixieland Casita

Charming one bedroom one bath guest house with separate living room located in the historic district of Dixieland. Just a few blocks from downtown Lakeland and only one mile from the beautiful 168 acre Bonnet Springs Park and the Florida Children's Museum. This cozy home is surrounded by all the best coffee shops, restaurants, beautiful lakes, and shopping/entertainment that Lakeland has to offer. For our coffee lovers, Hillcrest Coffee is only 500 feet from our Dixieland Bungalow.

ValueFamilyOutdoor spaces

Top guest favorite
Guesthouse in Lakeland
4.9 out of 5 average rating, 146 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.

LocationValueAccuracy

Top guest favorite
A wooden dock extends over the calm waters of Lake Howard, bordered by lush grass on either side. A sign indicating 'Private Property' stands at the dock's entrance, while the clear blue sky is dotted with fluffy white clouds in the background.
Guesthouse in Winter Haven
4.98 out of 5 average rating, 125 reviews

Charming Lakeside Cottage

Escape to our cozy lakeside cottage, featuring a dock that’s perfect for watching sunrises, fishing, and launching your kayak. The property is on Lake Howard, which is part of the Winter Haven Chain of Lakes. Inside, you’ll find a fully equipped kitchen and comfortable living space for unwinding. Located just a short drive from the excitement of Legoland and Disney World, you can easily explore the area’s attractions while having a peaceful haven to return to.

ValueLocationBathroom

Top guest favorite
Guesthouse in Lakeland
4.92 out of 5 average rating, 116 reviews

La Casita Azul

The Little Blue House is a studio,guest house in our backyard. 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.

ValueLocationKitchen

Top guest favorite
A bedroom is presented with a spacious bed featuring a patterned quilt and multiple decorative pillows. Natural light fills the room through window treatments. Sliding doors lead to an en-suite bathroom, and a wall-mounted television is positioned for easy viewing.
Guesthouse in Lakeland
4.99 out of 5 average rating, 111 reviews

Charming Guesthouse A

This brand new apartment, one bedroom, one bath (one queen bed and one full folding bed)and full kitchen located in North side Lakeland with easy access to I-4, Orlando or Tampa 45 minutes away from Disney, 35 from Legoland, 40 from Bush Garden, and 35 from Ibor City. College:15 minutes from Florida Southern College and 20 minutes from both Florida Polytechnic University and Pol State College.

LocationFamilyHospitality

Top guest favorite
The living room features a gray sofa with yellow accent pillows and a coffee table. A circular dining table for four is visible in a nook area, with a kitchen accessible in the background. A wall-mounted TV and large windows allow natural light in.
Guesthouse in Lakeland
4.99 out of 5 average rating, 108 reviews

*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.

LocationValueComfort

Guest favorite
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, 186 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

LocationValueDecor

Top guest favorite
A cozy sleeping area features a spacious bed with a soft throw blanket draped across the foot. An antique-style desk and chair are positioned nearby, while a wall-mounted television and framed artwork are visible. Unique pendant lighting provides a warm glow.
Guesthouse in Lakeland
4.94 out of 5 average rating, 338 reviews

Downtown Lakeland - Cozy Guest House Studio

Come relax or explore Lakeland in this cozy guest house in a quiet neighborhood, and yet centered located.

FamilyValueGetting around

Top guest favorite
A serene outdoor area features a decorative fountain surrounded by pavers. Lush grass and mulch create a natural border. In the background, a pool reflects sunlight, while lounge chairs and an outdoor seating area are arranged for relaxation.
Guesthouse in Lakeland
4.94 out of 5 average rating, 445 reviews

Quaint and Charming Pool Cottage....

Beacon Hill Historic District neighborhood is centrally located near downtown and Lake Hollingsworth.

FamilyValueDecor

Guest favorite
A modern living room features a grey sectional sofa, a flat-screen TV mounted on the wall, and a minimalist coffee table. Light wood flooring complements the space, where artwork decorates the walls and a ceiling fan enhances airflow. Kitchen appliances are visible in the adjacent area.
Guesthouse in Lakeland
4.97 out of 5 average rating, 313 reviews

Modern Retreat w/Privacy-Parking

Kick back and relax in this calm, stylish space. Your privacy and comfort is our goal

ValueFamilyAccess

Popular amenities for Lakeland guesthouse rentals

When is the best time to visit Lakeland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$15,696 GYDG$16,114 GYDG$16,533 GYDG$16,951 GYDG$14,858 GYDG$14,440 GYDG$14,649 GYDG$14,858 GYDG$14,021 GYDG$14,649 GYDG$15,696 GYDG$15,277 GYD
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