
Guest house holiday rentals in Lakeland
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Top-rated guest house rentals in Lakeland
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

Cozy patio level studio In Historic district
This cozy Patio level studio is on our homes property, it has a KITCHENETTE, WITH LIMITED COOKING. It is nestled in the Historic District of Lakeland and mere steps from Florida Southern a Frank Lloyd Wright designed campus, a tour is recommended! Our cobblestone streets take you to unique neighborhood restaurants. We are walking distance of beautiful downtown Lakeland. We are between two lakes- Lake Hollingsworth, a great 3+ mile walking/running path and Lake Morton which is a bird paradise.

Sunshine Studio + Courtyard, mins historic 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) SEU(1 mile) 17 mins from SUN N FUN!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.

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.

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, screened front porch, fire pit dock & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks, stand up paddle board, 4 seater 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!

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.

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.

Hickory Breeze Guest House
We invite you to come and enjoy our little piece of country in north Pasco County, Florida! Not fancy, but comfortable is our objective for our guests! We are not a business (nor are we owned by a business) therefore we do not conduct our hospitality like a business, but rather as hosts looking to meet and make new friends! We do all our own cleaning and set-up in the guesthouse so that we know it is done the way we would do it for our own family.

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.

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.

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.
Popular amenities for guest house rentals in Lakeland
Family-friendly guest house rentals

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

New Modern Guest House! Great location. Smoke-Free

Cozy Independent Studio

Charming 2BR Guesthouse Near Downtown Lakeland

Kissimmee Studio

Beauty & Beast Guest House, Near Disney, Sleeps 4

The Lake Hunter Hideout

Cozy studio for perfect get away
Guest house rentals with a patio

Sweet Escape

"Little Blue House" Getaway Near the Disney Parks

Cozy Oaks Suite

Florida Paradise

Downtown Stylish Studio (Florida Southern College)

Orlando Private Tiny Guest House

Charming Dixieland Casita

Sunshine guesthouse
Guest house rentals with a washing machine and dryer

Spacious Lkld Guest House 2/1

*Modern* Guesthouse steps to Lake Hollingsworth

Relaxing Lakeland Getaway Near Downtown & Lakes

Private Clean Lakeland GuestHome

Under The Oaks Cottage

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

Modern Guest Studio

Charming Guesthouse
When is the best time to visit Lakeland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £58 | £60 | £62 | £61 | £55 | £53 | £52 | £52 | £50 | £52 | £55 | £54 |
| 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 guest house rentals in Lakeland

Total holiday rentals
Explore 50 holiday rentals in Lakeland

Nightly prices starting at
Lakeland holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 4,110 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
50 of Lakeland holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Lakeland rentals

4.8 Average rating
Lakeland stays are highly rated by guests – averaging 4.8 out of 5!
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- Walt Disney World Resort
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