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Guest house holiday rentals in Winter Haven

Find and book unique guest house rentals on Airbnb

Top-rated guest house rentals in Winter Haven

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

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Top guest favourite
Guest house in Lakeland
4.95 out of 5 average rating, 207 reviews

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!

Guest favourite
The kitchen area features a modern design with wooden accents, including a small bar table with two stools. A black refrigerator and white microwave are present, alongside a sink and neatly arranged kitchen shelves. Natural light enters through a nearby window.
Guest house in Winter Haven
4.94 out of 5 average rating, 110 reviews

Winter Oasis

Escape to Winter Oasis, a serene retreat between Tampa and Orlando. Nestled in Winter Haven, our cozy guesthouse offers a haven for travelers seeking tranquility near major attractions. Whether you're exploring Disney's magic, enjoying Universal Studios' thrills, or simply unwinding in central Florida's beauty, our guesthouse is your perfect base. Relax in the comfortable outdoor area, cook in the fully equipped kitchen, or enjoy drinks on the private patio. Book your stay at Winter Oasis today!

Guest favourite
A compact bedroom features a spacious bed adorned with a white quilt and decorative towels shaped like a heart. A soft, brown armchair is placed beside a small nightstand, with a lamp providing warm light. A neutral rug covers the floor, complementing the room's decor.
Guest house in Lakeland
4.97 out of 5 average rating, 134 reviews

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.

Guest favourite
A screened-in pool area features a clear, inviting swimming pool with a light blue surface. Two striped lounge chairs are positioned beside the pool, and a small seating arrangement is visible in the background, providing a space for relaxation and outdoor enjoyment.
Guest house in Lake Alfred
4.93 out of 5 average rating, 198 reviews

Adorable Agave Suite w/ private pool and entrance

Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your “shome” away from home. Upon entry of the the property you will find a private entrance, covered parking, private screened in pool and mature trees. Your guesthouse comes equipped with 1 cozy queen size bed, pull-out sofa bed, walk-in shower, kitchenette, smart tv, wifi and more. Looking to explore? We are centrally located to your nearest parks & Florida attractions. Close to fishing docks & bike trails.

Top guest favourite
A living area features a beige sofa adorned with decorative pillows, positioned across from a wooden dresser and a flat-screen television. A geometric area rug is placed on the light wood flooring, while a soft light enters through sheer curtains covering a window.
Guest house in Bartow
4.79 out of 5 average rating, 135 reviews

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.

Top guest favourite
The quaint lakefront cottage is framed by large, leafy trees and draped with Spanish moss. A gravel entrance leads to a welcoming porch, featuring large screened windows. Lush greenery surrounds the property, creating a natural, serene setting.
Guest house in Lakeland
4.98 out of 5 average rating, 272 reviews

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!

Guest favourite
A serene lakefront scene captures a sparkling pool surrounded by palm trees at sunset. The sky features vibrant hues of orange and purple, reflecting in the calm water. Two lounge chairs are positioned beside the pool, creating a peaceful retreat.
Guest house in Winter Haven
4.87 out of 5 average rating, 282 reviews

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

Guest favourite
A spacious room features a queen size bed with a neatly arranged white blanket. Light tiles enhance the bright atmosphere, while a barn-style door leads to a private bathroom. A small kitchenette area with dark cabinetry and a modern sink is visible in the background.
Guest house in Winter Haven
4.81 out of 5 average rating, 275 reviews

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!

Top guest favourite
A spacious pool area features a clear, inviting pool surrounded by a tiled deck. Bright yellow sun loungers and a large red umbrella offer shaded seating. A decorative swan float rests in the water, while various potted plants enhance the serene atmosphere.
Guest house in Auburndale
4.97 out of 5 average rating, 249 reviews

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.

Top guest favourite
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.
Guest house in Winter Haven
5 out of 5 average rating, 106 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.

Top guest favourite
Guest house in Auburndale
4.97 out of 5 average rating, 196 reviews

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.

Top guest favourite
A cozy bedroom features a tufted gray headboard above a neatly made bed with white linens. Decorative pillows are arranged on the bed, and whimsical letters spelling 'DREAM' adorn the wall above. Two bedside tables with lamps provide a soft glow.
Guest house in Four Corners
4.98 out of 5 average rating, 519 reviews

Quiet Room Close to Disney and Attractions

Quaint and quiet retreat just minutes from attractions. Private in-law suite and bathroom, detached from main house. Features all the basic amenities of a hotel room with the feeling of home. Room is perfect for up to three persons. Queen bed and additional sleeper sofa. Located in Reunion Resort. There is a pool, gym, and spa located within the resort but not on the property and is for Reunion club members only.

Popular amenities for guest house rentals in Winter Haven

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Quick stats about guest house rentals in Winter Haven

  • Total holiday rentals

    Explore 20 holiday rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 1,700 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

    20 of Winter Haven holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Haven rentals

  • 4.8 Average rating

    Winter Haven stays are highly rated by guests – averaging 4.8 out of 5!

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