Guesthouse vacation rentals in Winter Haven

The image reveals an inviting courtyard with a patio table and umbrella, surrounded by greenery. Inside, a modern dining area is visible with a wooden table and sleek black chairs, complemented by tasteful wall art and bright lighting.

4.96 out of 5 average rating, 178 reviews

Sunshine Studio +Private Courtyard, near SEU, FSC

Nestle into this cozy, NEWLY remodeled studio! It is centrally located in Lakeland and 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!

Guesthouse in Winter Haven

A cozy outdoor seating area is illuminated by string lights overhead. Two dark-chairs are positioned around a circular fire pit surrounded by colorful plants and greenery. A relaxing lounge chair is situated in the corner, enhancing the inviting atmosphere of the garden space.

4.95 out of 5 average rating, 219 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 !

A beautifully arranged dish of shrimp is presented on a wooden board, accompanied by a glass of red wine. Soft seating is visible in the background, with a wall featuring the text 'Nineteen Sixty-One'. The setting conveys a modern dining experience.

4.98 out of 5 average rating, 105 reviews

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.

Guesthouse in Lake Alfred

The Agave Suite sign is displayed prominently on a blue wall, alongside a decorative hanging lantern. Lush green plants provide a natural frame, enhancing the peaceful outdoor setting. The surroundings are well-maintained, contributing to the welcoming entrance of the guesthouse.

4.94 out of 5 average rating, 174 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.

A wooden treehouse stands elevated among lush greenery, featuring rustic architecture with wooden siding and a sloped roof. Surrounding foliage includes tall trees and dense underbrush, creating a natural setting. The ground is covered with leaves, indicating a serene, wooded environment.

4.89 out of 5 average rating, 111 reviews

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.

Guesthouse in Winter Haven

A private pool area is highlighted by a circular pool, surrounded by a stone patio and lush foliage. Lounge chairs are positioned near the edge, offering views of the lake. Palm trees tower in the background against a backdrop of blue skies and scattered clouds.

4.88 out of 5 average rating, 273 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 ****

Guesthouse in Lake Hamilton

A single basin farmhouse sink is positioned beneath a window, surrounded by light wood countertops. To the side, a modern gold faucet complements the clean design. Kitchen utensils are organized in a holder, while two decorative bottles labeled 'SAVES' and 'HANDS' are placed nearby.

4.89 out of 5 average rating, 247 reviews

Luxury Cottage Near Legoland & Chain of Lakes

The Old Florida Cottage, in the quaint community of Lake Hamilton, just 5-miles from Legoland, less than an hour from Disney, and minutes away from the only public boat access to Lake Hamilton, is your perfect getaway! Enjoy a fully-equipped kitchen, a luxurious suite and modern bathroom, surrounded by Old Florida decor. We look forward to welcoming you to the cottage, with its own entrance and dedicated parking, located on a quiet street. Your home away from home!

Guesthouse in Winter Haven

An ornate black iron gate stands prominently at the entrance, framed by a porch area. The gate features intricate designs and opens to a path leading into a garden space, with potted plants lining the sides, creating an inviting passage.

4.88 out of 5 average rating, 193 reviews

Brutus Way Cottage, a cosy hide away

Enjoy a quick get away at Brutus Way Cottage. It is located to the rear of Lili Haven Bed N Breakfast. On your picturesque drive around Lake Howard, with its walking trail, you will take a right onto a quaint curvy lane known as S. Lake Cannon Drive NW . Be my guest at the cottage surrounded by flowers ; the cottage is nestled in the trees to the back past the Iron gates. Use of the Laundry room available upon request.

Guesthouse in Four Corners

The exterior features a two-story yellow house with a balcony and white railings. A staircase leads to the upper level, flanked by greenery. A paved driveway is visible, accommodating a parked vehicle. The surrounding landscaping includes well-maintained shrubs and grassy areas.

4.98 out of 5 average rating, 484 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.

A charcoal grill sits on a stand, flames flickering atop the grates, indicating it is in use. A wooden picnic table is positioned nearby, surrounded by scattered leaves, creating a cozy outdoor dining space.

4.98 out of 5 average rating, 248 reviews

Modern lakeside retreat by SEU and FSC

This 1/1 lakefront historic cottage, built in 1920, 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 and fishing poles are provided for your enjoyment during your stay. Come unwind and enjoy the lake views from the hammock and private beach!

4.97 out of 5 average rating, 230 reviews

A private pool area is enclosed by a screened enclosure, providing a serene environment. Ambient lighting highlights the water's surface, while various seating options including chairs and a table are set up alongside the pool. A playful inflatable float is visible in the water.

Guesthouse in Auburndale

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. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.