Guesthouse vacation rentals in Winter Haven

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Top-rated guesthouse rentals in Winter Haven

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Guest favorite

Guesthouse in Lakeland

4.96 out of 5 average rating, 187 reviews

Swan City Studio + Cozy Courtyard, near downtown

Your cozy retreat awaits you in Swan City 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!

Guest favorite

An inviting outdoor patio is presented, featuring comfortable seating on a woven couch and armchairs under a vibrant blue umbrella. Lush greenery and palm trees surround the area, adding to the tranquil ambiance, while a charming two-story building serves as a backdrop.

Guesthouse in South Lake Morton Historic District

4.89 out of 5 average rating, 184 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.

Top guest favorite

A charming exterior of the detached suite is framed by lush greenery and colorful landscaping. A patio area with a table and four chairs is visible, along with a sun umbrella. Soft lighting enhances the welcoming ambiance during the twilight hours.

Guesthouse in South Lake Morton Historic District

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.

Guest favorite

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.

Guesthouse in Lake Alfred

4.94 out of 5 average rating, 178 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

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.

Guesthouse in Winter Haven

4.87 out of 5 average rating, 278 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 favorite

A bright bedroom features a spacious bed with white linens and decorative pillows. Light-colored walls are complemented by a ceiling fan. Natural light enters through a nearby window, and simple decor adds a relaxed feel. A chair is placed beside the bed for added comfort.

Guesthouse in Lake Hamilton

4.89 out of 5 average rating, 259 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!

Top guest favorite

A serene pool area is enclosed by a protective screen, featuring a clear swimming pool surrounded by a tiled patio. A comfortable seating area is visible in the background, with a stylish egg chair. Lush greenery enhances the tranquil setting.

Guesthouse in Auburndale

4.98 out of 5 average rating, 240 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.

Guest favorite

An inviting sleeping area features a spacious bed adorned with decorative pillows and a quilt. A window allows natural light to fill the room, complemented by soft curtains. A ceiling fan circulates air, while a chair and mirror provide additional functional touches.

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.

Top guest favorite

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.

Guesthouse in Four Corners

4.98 out of 5 average rating, 492 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.

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, 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

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

4.87 out of 5 average rating, 113 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

The calm waters of Lake Ariana reflect a stunning sunset, featuring a gradient of orange, pink, and deep blue hues. Silhouettes of trees and a boathouse are visible along the shoreline, adding depth to the serene landscape.

Guesthouse in Auburndale

4.98 out of 5 average rating, 174 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.