
Guesthouse holiday rentals in Lakeland
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Top-rated Guesthouses in Lakeland
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

Private Clean Lakeland GuestHome
Guests love our spacious and charming fully updated and renovated private guest home, just a short drive from Disney and Universal Orlando, Busch Gardens, and the beaches of Tampa Bay! Take an evening stroll to one of the serene surrounding lakes. Adjacent to famous Lake Hollingsworth and within close proximity of downtown Lakeland and the RP Funding Center. Perfect for your next getaway including High speed Wifi, 4K 55” TV with Netflix, private laundry & everything you need for your vacation!

Sunshine Studio + Courtyard, Firepit, near downtwn
Your cozy retreat awaits you in Sunshine Studio! It is centrally located in Lakeland, a short drive from downtown, Florida Southern College (1.4 miles) Southeastern University (1 mile) The studio comes fully equipped with everything you need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the well appointed modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Private parking is just a few steps down the pathway through the courtyard from your door!

The Studio - LKLD
The Studio, stylish and comfy, is located on our home property. With easy access to I-4, you are a short distance from Tampa, Orlando, and many of our beautiful beaches! You are also a 15 minute drive to Southeastern University, Florida Southern College, downtown, and many of our amazing and unique local businesses! With a central location like this, there’s nowhere you can’t go. Nestled in a quiet neighborhood, it’s the perfect weekend stay! Disclaimer: There are chickens & roosters around.

Serenity at Success
Nestled in the heart of the Lake Morton Historic District, this completely detached private suite offers both charm and convenience. Just a 2-min walk to Lake Morton, home to Lakeland’s famous swans, and only half a mile from Lake Hollingsworth, a favorite spot for walking, running, and cycling. FSC is just one block away, making this an ideal stay for campus visitors. Enjoy a leisurely one-mile stroll to downtown Lakeland, where you’ll find an array of restaurants, bars, and boutique shops.

Simple Apartment in quiet suburb
This property is about 1 hour from Tampa & Orlando, away from traffic and noise. This 1 bedroom apartment offers a comfortable bed with simple amenities. We are not far from many attractions such as Disney, Universal Studios, LegoLand, Busch Gardens, Seaworld, and more. The property has its own private entrance to come and go as you wish. Pickelball are courts nearby as well as grocery stores, local coffee shops, and local restaurants - all within 5 min. driving distance of the property.

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.

Private Carriage Studio, Mins to Dwntwn, FSC
A lovely space to unwind and relax after a busy day whether it is work or play. Awake refreshed and ready for a day exploring Lakeland and highly desired surrounding cities via this clean, sunny studio with full kitchen, bathroom, and washer/dryer. Head out and wander through the nearby farmers’ market every Saturday in downtown Lakeland and pick up local ingredients to later craft a meal in the fully stocked kitchen. 1.2 miles from Florida Southern!! 2.9 miles from SEU. (Queen Bed)

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.

Adorable 1 bedroom Guesthouse near Lego Land
This is a beautiful and private place offers a queen size bed, newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! We are located less than 8.6 miles from Legoland & under 6.2 miles from the Lake Myrtle Sports complex. Winter Haven is halfway between Orlando and Tampa. Around 29 miles to Disney World, Universal and Sea World. Around 38 miles to Bush Gardens, Dali museum, Aquarium and much more!

Private Poolside Villa
Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. The apartment is behind my personal home with no connecting doors. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Cozy 2-bedroom guesthouse on the lake
Enjoy a relaxing getaway on the beautiful Lake Ariana. Two bedrooms with queen beds comfortably accommodating four adults. Fully equipped kitchen and full bathroom with tub. Laundry room with washer and dryer. Private parking with plenty of room for boat or jet skis. Private entry with hosts on premises. Camera at exterior door for security. The guesthouse is behind the main home. There is not a view of the lake from inside the guesthouse.

Modern lakeside retreat by SEU and FSC
This 1920’s 1 bedroom 1 bath lakefront historic cottage 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, pedal boat, and fishing poles and tackle are provided for your enjoyment. Come unwind and enjoy the lake views from the hammock and private beach!
Popular amenities for Lakeland guesthouses
Family-Friendly guesthouses

New Modern Guest House! Great location. Smoke-Free

Grand Room

Under The Oaks Cottage

2 King Beds + Fireplace + Fenced Yard Retreat

MR 1 - Comfort and Privacy

Cozy Guesthouse 60% Off Monthly Rate Inc Utilities

Studio Zen

Cozy guest house w/ fenced yard and hot tub
Guesthouses with a patio

Kissimmee Studio

Florida Paradise

Thousand Oaks Peaceful Studio with Private Pool

Private Apt D Near Downtown/ Chain of Lakes

Downtown Stylish Studio (Florida Southern College)

Cottage in Dixieland

Charming Guesthouse A

Sunshine guesthouse
Guest house rentals with a washing machine and dryer

Spacious Lkld Guest House 2/1

Quiet Guesthouse in S. Lakeland, Fast Wi-Fi.

Cozy Oaks Suite

*Modern* Guesthouse steps to Lake Hollingsworth

The Lake Hunter Hideout

🌟Historic 1924💕Carriage House🏡Quaint & Cozy☀️🪂

Modern Guest Studio (Private) Pool / Spa available

Cozy Winter Haven Guesthouse 1
When is the best time to visit Lakeland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $138 NZD | $141 NZD | $146 NZD | $145 NZD | $131 NZD | $125 NZD | $122 NZD | $124 NZD | $117 NZD | $131 NZD | $131 NZD | $138 NZD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about guesthouse rentals in Lakeland

Total holiday rentals
Explore 50 holiday rentals in Lakeland

Nightly prices starting at
Lakeland holiday rentals start at $87 NZD per night before taxes and fees

Verified guest reviews
Over 3,810 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Lakeland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Lakeland rentals

4.9 Average rating
Lakeland stays are highly rated by guests—averaging 4.9 out of 5!
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- Universal Studios Florida
- Orange County Convention Center
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- Disney Springs
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