Guesthouse vacation rentals in Lakeland

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!

4.89 out of 5 average rating, 171 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.

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, 170 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.

Guesthouse in Downtown Lakeland

4.82 out of 5 average rating, 111 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.

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, 242 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.

5 out of 5 average rating, 247 reviews

Guesthouse in Orlando

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

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, 245 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

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.

4.86 out of 5 average rating, 111 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, 228 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.