Holiday houses in Lakeland-Winter Haven Metropolitan Area

4.86 out of 5 average rating, 140 reviews

Guest suite in Lakeland

Private Studio Suite

🧳 Perfect for a solo traveler or couple looking to visit the peaceful city of Lakeland. 📍Located about 40 minutes from Tampa and an hour from Orlando, in the family friendly area of Lakeland Highlands. - There’s nearby trails, grocery stores, convenience stores and eateries. - Polk Parkway is less then 10 minutes away, it’s the quickest route to get to i4. 🏠 The suite includes a private entrance with full bathroom and backyard area. 🚗 Free Parking Space(s) 👐🏽 Flexible & Contactless Entry

4.96 out of 5 average rating, 178 reviews

Guesthouse in Lakeland

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!

5 out of 5 average rating, 126 reviews

Top 1% Stay – Cozy Lakefront with Hand-Fed Swans

In the Heart of Lakeland, FL... on the Banks of Lake Morton! Nestled between the Historic District and beautiful South Lake Morton Historic District... (or as we like to call it, "Swan Lake") this property is located in easy walking distance to: Restaurants & Shopping Lakeland Public Library The Polk Museum of Art Historic Downtown Lakeland Lake Hollingsworth Florida Southern College Lake Mirror Hollis Gardens AND of course... Lake Morton Take it easy at this unique and tranquil getaway.

4.89 out of 5 average rating, 111 reviews

Guesthouse in Lakeland

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.

4.95 out of 5 average rating, 237 reviews

Apartment in Auburndale

Ariana Place - Tree House Like Lakefront Views

An Upstairs Sumptuous Tree house (like) Apt on Lake Ariana Waterfront. Upper Outside Deck with chairs & table. Quiet and tranquil with Hi-Speed Wifi for Business Travelers, Smart Antenna TV and Incredible Views for Romantic Get-Aways. Located near Disney, Legoland & Busch Gardens in Central Florida. Luxurious Bedding, Full Kitchen with Coffee & Wine Bar. One Complimentary Bottle of Cabernet per Stay. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly

4.96 out of 5 average rating, 982 reviews

Treehouse in St. Cloud

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Superhost

4.84 out of 5 average rating, 161 reviews

Hollingsworth Pool Home

This artistic, craftsman-style pool home is regally situated on a red brick street in Lakeland's beloved Lake Morton Historic District. Centrally located, with Lake Hollingsworth just 2 blocks away, the Hollingsworth House is also walking distance to Cob & Pen, Concord Coffee, and the trendy Dixieland neighborhood where you can shop at antique and boutique shops. The large pool is surrounded by 8 foot privacy fence and a fully-fenced in backyard. Free driveway parking.

4.97 out of 5 average rating, 104 reviews

“Our Nest” Cozy Retreat Near Downtown & FSC Campus

Welcome to Our Nest—a peaceful retreat along Lakeland’s historic brick streets. Just steps from Frank Lloyd Wright’s iconic architecture, this one-bedroom stay offers a plush king bed, stocked kitchen, fast Wi-Fi, smart TV, and a private patio perfect for slow mornings or quiet evenings. Walk to Lakes Morton and Hollingsworth, explore cafés, or relax as swans drift by. Clean, quiet, and thoughtfully prepared—the kind of place we’d want to find ourselves in.

Superhost

4.82 out of 5 average rating, 121 reviews

❤️ Brand New Modern Studio Perfect for Long Stays

This modern and private modern studio has space for three people, located in one of the best areas of Lakeland, less than 1 mile from Lake Hollingsworth, close to downtown Lakeland and major universities. Close to Disney World and 1 hour from Clear Water Beach. It is a central but quiet neighborhood, close to Publix supermarket, restaurants, gas station and laundry. Without a doubt, a cozy space !!! Don’t hesitate to ask if you have any questions.

4.96 out of 5 average rating, 134 reviews

Cozy Lake House Retreat - Amazing Views !

Welcome to our lake house retreat in Lakeland, Florida. You can enjoy a peaceful getaway with beautiful sunset views and tranquil waters during the evenings, and still visit major cities such as Orlando and Tampa during the day which are less than an hour away. Minutes from Southeastern University, Florida Southern, Lake Hollingsworth, and other attractions in the Lakeland area.

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Popular amenities for Lakeland-Winter Haven Metropolitan Area holiday rentals

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Other great holiday rentals in Lakeland-Winter Haven Metropolitan Area

4.99 out of 5 average rating, 94 reviews

Tiny home in Lakeland

Charming Tiny House on 5 acres with POOL/ HOT TUB

MaribelRating, 5 starstoday

The Tiny House was a pleasant surprise. It is so charming, comfy and felt right at home. It has everything a big place would have and then some. The bed was very comfortable with amazing linens. Located in a great area and always felt safe during my solo getaway! Looking forward to visiting again! MM

5 out of 5 average rating, 5 reviews

Cozy Central Florida Getaway

BelkisRating, 5 stars1 day ago

Jackie’s home was spacious, very clean, well decorated and had anything we needed. She was very responsive. Great host!

5 out of 5 average rating, 9 reviews

Brisa sur

JoeRating, 5 stars1 day ago

Alayn was a gracious host. We had everything we needed for a perfect stay. Highly recommend! Thank you for hosting us! Joe and crew

5 out of 5 average rating, 46 reviews

Freshly Updated Luxury Downtown Home

DeverouxRating, 5 stars1 week ago

We had a wonderful stay at Melissa's place in Lakeland! From booking to checkout, everything was seamless. Melissa provided clear check-in instructions and the door code system worked perfectly. The home was incredibly well-stocked - full kitchen with Keurig and French press, all toiletries provided, and thoughtful extras like a basket of "forgot items" (toothbrushes, etc.). As a family with kids, we loved finding child plates, utensils, pack n play, and high chair ready for us. Having laundry facilities with detergent was so convenient. Melissa's communication was excellent - she checked in at just the right times and her local guidebook recommendations were spot-on. The location was perfect for exploring Lakeland. This truly felt like a home away from home with every detail thoughtfully considered. Melissa goes above and beyond to ensure her guests have everything they need for a comfortable stay. Highly recommend - we'll definitely be back!

4.98 out of 5 average rating, 40 reviews

"Large" Studio

FrankRating, 5 stars3 months ago

Great location for FSC visit. Unit just as published. Would come again.

4.89 out of 5 average rating, 117 reviews

Private room in Lakeland

Lk Morton Bungalow- #2 Full near the Colleges

JacksonRating, 5 stars2 weeks ago

Amazing place! The house is super cozy, well-equipped, and very well located in Lakeland. The atmosphere is family-friendly, quiet, and peaceful. We were in town for the Swan City music festival, which was a very interesting and fun experience. Highly recommend!

5 out of 5 average rating, 4 reviews

Cozy Retreat in the city

KeriRating, 5 stars3 days ago

Great host & property with lots of good complimentary food & hygiene products. Would stay again.