Holiday rentals 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

Guest house 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.

4.82 out of 5 average rating, 114 reviews

Guest house in Lakeland

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.

4.89 out of 5 average rating, 111 reviews

Guest house 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

Flat 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.

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, 117 reviews

Hidden Ruby-Apartment with Kitchen and Laundry

Your family will be close to everything when you stay at this centrally-located place. Within walking distance to restaurants, major grocery stores, parks, and much more. Midway between major cities of Orlando and Tampa for the urban seekers. Reserved guest parking, front porch sitting area, washer and dryer, work station, and a children-safe environment. This apartment was designed to accommodate all of your needs.

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Popular amenities for Lakeland-Winter Haven Metropolitan Area holiday rentals

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Wifi

Pool

Free parking on premises

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Other great holiday rentals in Lakeland-Winter Haven Metropolitan Area

4.95 out of 5 average rating, 201 reviews

Private room in Lakeland

1Lake, king suite, priv bath,by parkway, colleges

CarlosRating, 5 stars1 month ago

Kary was very pleasant, helpful and resposive to messages. Room was very pleasant, roomy, and had many amenities. Didnt have time to get in the pool but it was a nice pool. Thank you Kary for allowing me to stay in your home.

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 stars1 day ago

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 stars2 days 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 stars2 days 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

4.95 out of 5 average rating, 212 reviews

Private room in Lakeland

Desirable South Lakeland Location.

LillieRating, 5 stars2 weeks ago

We stayed at Chris' place after flying into Lakeland. It was close to the airport and easy to find. We loved the place. It's well decorated and very clean. I stayed there with my mother and two children on the pull-out couch. I'd definitely go back 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 stars4 days ago

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