Guesthouse vacation rentals in Winter Haven

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Winter Haven

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

A cozy outdoor seating area is surrounded by lush greenery and vibrant potted plants. A fire pit with wood sits at the center, while string lights provide soft illumination. A comfortable couch is adorned with decorative pillows, enhancing the inviting atmosphere for relaxation.

Guesthouse in Winter Haven

4.94 out of 5 average rating, 218 reviews

The Paradise Hide Away

This is a beautiful and private place newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! Talk to me if you need different check in/out times? Dogs are allowed with permission. There is a $200 fully refundable pet security deposit to cover any damages that may occur since Airbnb doesn’t cover damages caused by pets plus a non refundable pet fee of $50 per pet for every 1-7 day period and must be paid before checking in !

Guest favorite

Lush landscaped gardens display vibrant flower beds filled with pink and purple blooms, bordered by neatly trimmed shrubs. Palm trees rise gracefully against a bright blue sky, with a serene waterfront visible in the background, enhancing the tranquil outdoor environment.

Guesthouse in Downtown Lakeland

4.82 out of 5 average rating, 106 reviews

Charming Dixieland Casita

Charming one bedroom one bath bungalow 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, which also features the newly renovated 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.

Guest favorite

An open living space features a comfortable green sofa and light-colored armchairs with decorative pillows. A kitchen area with bar stools is visible in the background, alongside a dining table. Natural light streams through the windows, illuminating a tasteful arrangement of plants on the coffee table.

Guesthouse in Davenport

4.89 out of 5 average rating, 184 reviews

Winsome Farm Guest House

*Rest, *Relax, *Refresh, *Renew Here! Business travel? Vacationing? Escape the hectic pace but be nearby to all Central Florida amusements, restaurants, shopping, theater. Mid-way between east and west coast beaches. Large screened back porch overlooks nature conservancy. Farm to table fresh vegetables and fruits in seasonal garden right out your door and daily fresh eggs, should you choose to cook in fully outfitted kitchen or electric grill outside.

Superhost

A sandy beach area is filled with colorful lounge chairs, shaded by green and yellow umbrellas. In the background, a towering volcano structure with cascading water is visible, surrounded by palm trees under a partly cloudy sky.

Guesthouse in Florida Center

4.81 out of 5 average rating, 238 reviews

Luxury 5 star home 3 min Universal/ Orlando City

Discover your home away from home in this inviting 1 bedroom, 1 bathroom guesthouse, designed for comfort and modern convenience. Nestled in a prime location, this cozy retreat offers easy access to popular theme parks, making it an ideal choice for fun-filled vacations. The bathroom suite has a rain shower just like you would expect in a 5-star Hotel, full kitchen, appliances and 2 TVs, one in the bedroom, and another in the living room.

Top guest favorite

A charming guesthouse is nestled among lush tropical vegetation, surrounded by diverse greenery and tall trees. Sunlight filters through the leaves, casting dappled light on the exterior and patio area, creating a serene and inviting atmosphere.

Guesthouse in Windermere

4.94 out of 5 average rating, 266 reviews

Paradise nook near Orlando's theme parks

A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

Superhost

A serene indoor pool area features a rock waterfall cascading into the clear water. Lush greenery surrounds the space, and bright light filters through the screened enclosure, creating a refreshing atmosphere.

Guesthouse in Lakeland

4.86 out of 5 average rating, 110 reviews

Luxury Cottage on Prestigious Million$ Property

Close to everything. Away from it all. Situated on 5 grassy acres and home to the Lewman family, this pristine south Lakeland home is fully fenced with a gated entry. The Guest House sits detached next to the main house with plenty of shared parking. Enjoy the outside without the worry of traffic. Free Wifi. We pride ourselves in providing a clean and safe home for you to make your own while you are here.

Top guest favorite

A circular seating area is created with two black lounge chairs set on a bed of mulch. In the center, a stone fire pit is surrounded by greenery. The background features a view of Lake Ariana, framed by trees and gently swaying Spanish moss.

Guesthouse in Auburndale

4.97 out of 5 average rating, 149 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.

Guest favorite

The exterior of the cottage features a charming blue door with a window grid design. A welcome mat is positioned at the entrance, complemented by a patterned brick pathway. Two black-framed windows provide natural light, enhancing the inviting appearance of the space.

Guesthouse in Lakeland

4.92 out of 5 average rating, 128 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

Superhost

A well-lit bedroom features a spacious bed with soft bedding and decorative pillows. A ceiling fan contributes to the airflow. A small bedside table and a closet enhance the room's functionality. The entrance door is visible, adding convenience to the layout.

Guesthouse in Orlando

4.76 out of 5 average rating, 155 reviews

Renovated Guesthouse Next to Universal/Disney/EPIC

Welcome to your ideal getaway! This beautifully appointed 2-bedroom, 1-bathroom vacation guesthouse offers everything you need for a memorable stay. Centrally located, this guesthouse is only 3 minutes away from Universal Studios and 15 min from Disney! This gem features 2 queen beds, private entrance, and free parking.

Guest favorite

A keypad entry system is positioned on the door, featuring numeric buttons and a keyhole beneath. The brushed metal finish reflects light, enhancing the modern appearance, while a simple design allows for easy access to the studio guesthouse.

Guesthouse in Orlando

4.91 out of 5 average rating, 261 reviews

Cozy Guesthouse Getaway

Welcome to our private studio guesthouse with queen mattress, full bath, kitchenette, mini fridge, microwave, coffee maker, WiFi, and cable TV. Convenient access to downtown, theme parks, beaches, and the turnpike. Perfect for the traveling business person or the amusement park visitor!