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Guesthouse vacation rentals in Winter Haven

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Winter Haven guesthouse rentals

Family-friendly guest house rentals

Guest favorite
A cozy outdoor seating area features a table with turquoise umbrella and four chairs surrounded by lush greenery. The cottage's brick facade and tiled roof complement the rural setting. A screened door leads into the interior, providing a welcoming entrance.
Guesthouse in Lake Wales
4.95 out of 5 average rating, 43 reviews

Country Cottage at Starr Lake

SteveRating, 5 stars2 months ago
Enjoyed my stay there. Felt at home the whole time. Enjoyed sitting outside with my cup of coffee, listening to the owls “talking” to each other. Very peaceful setting. Beautiful trees. Enjoyed watching all (9) of the cats playing and walking around in the yard. The blueberry muffins were awesome! Thank you for a lovely experience.
Guest favorite
The exterior of a single-story house is showcased, featuring a combination of light peach-colored walls and stone accents. A neatly manicured lawn and small hedges frame the entrance, which is marked by a covered porch. A driveway leads to a garage door on the left.
Guesthouse in Orlando
4.83 out of 5 average rating, 340 reviews

Nice Brand New Studio !!

MitchellRating, 5 stars1 month ago
Great little place in a cul-de-sac. Alvaro was incredibly friendly and helpful. I would gladly stay again.
A serene path is framed by tall bamboo stalks bending over, creating a natural archway. The ground is covered with soft earth and scattered leaves, inviting peaceful strolls through the tranquil environment of the bamboo forest.
Guesthouse in Kissimmee
4.91 out of 5 average rating, 55 reviews

Bird Watchers Delight - home close to Disney WIFI

TimRating, 5 stars2 months ago
quiet location surround by a busy area. lots of stuff do do in the area but it was nice having a quiet place to come back to. I really enjoyed having the screened in porch
Top guest favorite
A wooden dock extends over calm waters, reflecting hues of orange and pink from the sunset. Surrounding vegetation adds a natural frame to the serene lake view, while the distant shoreline is faintly visible against the evening sky.
Guesthouse in Lakeland
4.98 out of 5 average rating, 242 reviews

Modern lakeside retreat by SEU and FSC

DeborahRating, 5 stars1 week ago
This is the best Airbnb I have ever stayed at. The host stocked the space with everything you could possibly need. Had the wonderful opportunity to meet Amanda - she is the best host!!! My son and daughter-in-law will book with her the next time they bring their son to SEU. And we will be back as well! HUGE SHOUT OUT to Amanda and Warren for all they did to accommodate us!
Superhost
An inviting outdoor pool area features a rock waterfall and is surrounded by a screened enclosure. Soft lighting enhances the tranquil blue water, while tropical plants can be seen in the background. A few chairs are positioned nearby for relaxation.
Guesthouse in Lakeland
4.86 out of 5 average rating, 110 reviews

Luxury Cottage on Prestigious Million$ Property

TonyaRating, 5 stars1 week ago
Awesome place! It accommodated my husband and I perfect. Very clean. Felt very safe, as it is in a wonderful neighborhood. Pool was very cool! Peacocks were fun to sit and watch each day! Megan was a great host and Stephanie was very friendly and helpful. We will absolutely stay here again.

Guest house rentals with a patio

Top guest favorite
The entrance to Legoland Florida is showcased, marked by a colorful arch adorned with large LEGO sculptures and the word 'LEGOLAND' prominently displayed. Paved pathways made of light and dark stones lead into the park, surrounded by vibrant designs on the ground.
Guesthouse in Winter Haven
4.95 out of 5 average rating, 63 reviews

Legoland On The Lake

VictorRating, 5 stars1 week ago
Nice place near Legoland. Would stay again.
Guest favorite
The exterior of the studio is depicted, showcasing a small porch with a chair. The entrance is flanked by vibrant plants, and a window with purple trim provides a pop of color against the light gray walls. A clear blue sky completes the scene.
Guesthouse in Kissimmee
4.96 out of 5 average rating, 56 reviews

Kissimmee Studio

LanceRating, 5 stars1 month ago
For the price - it's the best Entire Home private place I have stayed on AirBnB. It's a quiet neighbourhood and you have a big backyard to chill. Katherine is a great host. Highly recommend.
Top guest favorite
A spacious bedroom features soft blue walls and a tiled floor. A comfortable bed is centered in the room, complemented by a bedside lamp. A dresser with a mirror stands nearby, and a closet door is visible. Light enters through a nearby door.
Guesthouse in Lakeland
4.96 out of 5 average rating, 26 reviews

Florida Paradise

JessieRating, 5 stars1 week ago
This was our 1st Air bnb experience, which upon our arrival, the host check in on us to assure all was as expected. It was… We did enjoy the environment and will call them again, when we return.
Guest favorite
Guesthouse in Lakeland
4.94 out of 5 average rating, 33 reviews

The Lake Hunter Hideout

JodyRating, 5 stars3 weeks ago
Great hosts, very friendly, in a nice neighborhood. A quant setting behind the hundred year old house with a nice outdoors seating deck just steps from the cottage. I would recommend this place if your are in the lakeland area and it's just 6 minutes to downtown restaurants.
Superhost
The exterior of a green garage apartment is shown, featuring a small staircase leading to the entrance. The surrounding yard includes landscaped elements like a patch of grass and mulch. The structure is shaded by nearby trees, with a clear blue sky above.
Guesthouse in Lakeland
4.7 out of 5 average rating, 10 reviews

Tree House Apartment in Dixieland

DavidRating, 5 stars1 month ago
Nice place, nice location. Comfortable.
Superhost
Guesthouse in Winter Haven
4.91 out of 5 average rating, 23 reviews

Nice Guesthouse With Pool & Nearby Boat Access

TheresaRating, 5 stars2 months ago
Chandra is a dream host!! Very responsive, cares for the comfort and needs of her guests. The pool house is roomy and comfortable. Kitchen is very practical for any cooking or baking needs. Chandra has so many thoughtful amenities in kitchen and bath. The location is 45 -60 minutes to Orlando, Bok Tower and Tampa. Affordable and comfortable for exploring all of Central Florida.
Guest favorite
A pathway made of concrete stepping stones is lined with white gravel, leading to a charming entrance of a small building. The surrounding area features minimal landscaping with green plants and trees visible, and a wooden fence encloses the space.
Guesthouse in Kissimmee
4.86 out of 5 average rating, 74 reviews

Unit B Apt Relax House

KevinRating, 5 stars2 weeks ago
Awesome stay. Would definitely stay again.
Guest favorite
A cozy living room area is furnished with two comfortable sofas, complemented by decorative cushions. A flat-screen TV is mounted on the wall, while a small side table holds a lamp. Natural light enters through two windows, enhancing the inviting space.
Guesthouse in Cypress Gardens
4.89 out of 5 average rating, 18 reviews

2 Bdrm near Legoland guesthouse

GeraldRating, 5 stars2 months ago
Great spot for legoland/ peppa pig theme park!!

Guest house rentals with a washer and dryer

Top guest favorite
An inviting living space features a combined dining and lounge area. A light wood dining table with white chairs is set beside a cozy couch and armchair arrangement. Natural light fills the room through large windows, complemented by a decorative rug and wall-mounted television.
Guesthouse in Lakeland
5 out of 5 average rating, 35 reviews

Spacious Lkld Guest House 2/1

AmandaRating, 5 stars2 weeks ago
We cannot say enough about how wonderful our stay was at Hailey and Nick’s Airbnb. It is an absolutely darling, clean and charming place. Hailey made our time above and beyond great with her kindness &!wonderful recommendations that allowed us to enjoy the best part of Lakeland in Tampa. This is by far our favorite Airbnb we have stayed at and we are so thankful.
Guest favorite
A single-story guesthouse is surrounded by a neatly landscaped yard, featuring a prominent tree in front. The house displays a modern façade with large windows and a black garage door. Soft evening light creates a welcoming atmosphere against a colorful twilight sky.
Guesthouse in Winter Haven
4.92 out of 5 average rating, 84 reviews

Comfy Guest House

JoeRating, 5 stars1 week ago
A perfect home away from home. I definitely will book again if available for my future stays.
Superhost
An inviting outdoor area includes a sparkling pool surrounded by lush greenery. Soft white drapes hang beside the pool area, offering a comfortable shade. A spa tub is visible in the foreground, with seating options arranged thoughtfully nearby, creating a relaxing retreat.
Guesthouse in Lakeland
5 out of 5 average rating, 3 reviews

Beautiful 1/1 pool + hot tub + pet friendly

StaciaRating, 5 stars3 weeks ago
This place was lovely. We enjoyed it very much. The floors, bathroom, and everything was super clean. The bed was comfy. The kitchen was well stocked. The pool and hot tub were awesome! My kids loved it! The backyard was so beautiful. You do the share the pool with other guests, since the main house is an air bnb also. This location was perfect for the Sun n Fun aerospace expo. About 17 min drive. We also got to see the blue angels fly right over the house while we were swimming!! Can’t beat that! I would definitely recommend this adorable little place! The host was always responsive and helpful.
Guest favorite
A light blue door with decorative glass features is set into a beige exterior, surrounded by stone accents. Potted plants are positioned near the entrance, and a welcome mat invites guests. Natural shadows play across the surface, creating a serene impression.
Guesthouse in Lakeland
4.87 out of 5 average rating, 98 reviews

Private Carriage Studio, Mins to Dwntwn, FSC

TinaRating, 5 stars1 week ago
Beau & Makenzie’s place was great for our 2 night stay as our house was getting tented for termites (a common thing for Florida if you aren’t from here). They were flexible with checking in and out and allowed us to bring our fur babies which was a HUGE relief! The neighborhood is beautiful and it’s very close to shops and restaurants. Not only would we stay here again, we’d recommend it to anyone else!
Superhost
A clear sign is displayed, indicating a no smoking policy. The sign features a simple design with a cigarette icon crossed out, emphasizing the smoke-free environment.
Guesthouse in Winter Haven
4.89 out of 5 average rating, 37 reviews

Oasis in the city, New in the market

MichaelRating, 5 stars1 day ago
I really enjoyed my stay at Walter’s place and would stay there again. Very scenic, clean, private, and safe. Walter was a great host, very friendly and personable. He treated me like a friend.
Top guest favorite
A bright living room features a gray sofa with two yellow cushions, complemented by a coffee table on a patterned rug. A circular dining table for four is visible, alongside two black chairs. Large windows provide ample natural light, creating an open and inviting space.
Guesthouse in Lakeland
5 out of 5 average rating, 72 reviews

*Modern* Guesthouse steps to Lake Hollingsworth

CindyRating, 5 stars3 weeks ago
Absolutely loved this place! We will definitely stay here again!
Top guest favorite
A large swimming pool is surrounded by tall palm trees, capturing vibrant colors of the sunset in the background. Lounge chairs are arranged around the pool's edge, providing a relaxing space for guests. Soft lights enhance the serene ambiance as twilight approaches.
Guesthouse in Four Corners
4.97 out of 5 average rating, 29 reviews

BeachGuyDave's Reunion Guesthome

MorganRating, 5 stars3 weeks ago
David was a fantastic host! He was quick to respond to any questions I might have had. The place is exactly like the pics and description. Very clean and homey. I highly recommend. Can’t wait to visit again!
Superhost
A circular hot tub is illuminated with blue lighting, featuring tiled edges and water cascading gently over the sides. The smooth, rounded surface showcases swirling water, creating a serene atmosphere within a well-designed outdoor space.
Guesthouse in Orlando
4.92 out of 5 average rating, 257 reviews

Modern Guest Studio (Private) Pool / Spa available

BrandiRating, 5 stars1 week ago
Had a great stay, communication was great. We had a small hiccup with the hot tub and problem was solved very quickly. The only thing I would complain about and not really complaining is there were cloths and a used towel hanging on the back of the bathroom door. No biggie and honest mistake by cleaners other then that the stay was amazing and felt like home away from home. Will stay again for sure

Quick stats about guesthouse rentals in Winter Haven

  • Total rentals

    20 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore

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  3. Florida
  4. Polk County
  5. Winter Haven
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