Guesthouse holiday rentals in Winter Haven

4.89 out of 5 average rating, 182 reviews

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.

4.96 out of 5 average rating, 183 reviews

Swan City Studio +Private Courtyard, near downtown

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

4.96 out of 5 average rating, 104 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.

4.98 out of 5 average rating, 106 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

4.94 out of 5 average rating, 176 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.

Superhost

Guesthouse in Winter Haven

4.87 out of 5 average rating, 276 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

4.89 out of 5 average rating, 257 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

4.88 out of 5 average rating, 196 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.

4.98 out of 5 average rating, 250 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!

Superhost

4.87 out of 5 average rating, 112 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.

4.97 out of 5 average rating, 238 reviews

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.