Holiday rentals in Lakeland-Winter Haven Metropolitan Area

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Lakeland-Winter Haven Metropolitan Area

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Lakeland

5.0 out of 5 average rating, 24 reviews

Vintage Styled Mid-Century 2/1 with Sunroom & Yard

Step into the past with modern comforts at our Lakeland, Florida, vintage mid-century modern home. Nestled on a quarter-acre next to Beacon Hill and Dixieland, our two-bedroom, one-bathroom home embodies Lakeland's charm. Explore Downtown Lakeland, Munn Park, Lake Hollingsworth, all just 10 minutes away. Relax in the fenced backyard, and bring along your pets! Venture to Tampa's Hard Rock Casino, downtown Tampa, Disney, Clearwater, St. Petersburg, and Orlando—all within an hour-and-a-half drive.

Guest favourite

Home in Lakeland

4.96 out of 5 average rating, 117 reviews

Cute, Historic District Home - GREAT LOCATION

Enjoy a stylish experience at this centrally-located place 5 mins from downtown Lakeland, 8 mins from I-4, 40 mins from Tampa and Orlando (Disney World/Universal), 1 hour from several beaches including Clearwater. 🐕 Pet friendly but you MUST include your pets in the reservation Nearby places of interest: - Downtown Lakeland - Southeastern University and Florida Southern College - RP Funding Center - Lakeland Linder International Airport - Polk Theatre - Circle B Nature Reserve - and more!

Guest favourite

Flat in Lakeland

5.0 out of 5 average rating, 24 reviews

Swan Lake Views/Walk to Downtown

Discover SWAN LAKE VACATIONS. Swan elegance meets city charm steps away. Highlights: • Lake Views • Downtown Stroll • King-sized bed • Modern Comfort • Full Kitchen • Semiprivate Patio • Between Tampa & Orlando Why Swan Lake Vacations? • Central Hub • Safety Assurance • Easy drive to beaches and Walt Disney World • Experienced Hosts Escape to Swan Lake Vacations—a place where swans grace the surroundings next to quaint downtown life. Book for a perfect blend of nature and urban comfort!

Guest favourite

Guest house in Lakeland

4.94 out of 5 average rating, 145 reviews

Swan City Studio +Private Courtyard, mins to dntwn

Enjoy your stay in Lakeland in our cozy, remodeled studio! It is centrally located in Lakeland and a short drive from downtown, Florida Southern College (1.4 miles) Southeastern University (1 mile) It comes fully equipped with everything you will need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the cozy modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Parking is just a few steps down the pathway through the courtyard from your door!

Guest favourite

Bungalow in Lakeland

4.99 out of 5 average rating, 101 reviews

Charming Bungalow with Front Porch

Enjoy peace and serenity at this centrally located, charming, 1920's bungalow in Lakeland. You will find the front porch an inviting spot to relax and unwind on this quiet street in the Lake Morton historical district. Downtown Lakeland, a Publix grocery store, Dixieland shopping, restaurants, bars and a liquor store are less than a five minute drive away. FSC, Lake Morton and Lake Hollingsworth with its 3 mile, paved walking trail are within a few, walkable blocks.

Guest favourite

Home in Lakeland

4.89 out of 5 average rating, 64 reviews

Charming and comfy apt near downtown

It doesn't matter if it's vacation time or if you're coming on a business trip, this charming and comfy house, has all the features and space to make you're stay comfortable and enjoyable. You can walk down the street to enjoy the beautiful view of Lake Hunter. We are close to the best Lakeland has to offer, 5 minutes away or less from downtown, Lakeside Village, local coffee shops, restaurants, and much more. Also roughly 45 min away from Tampa or Orlando.

Guest favourite

Home in Lakeland

5.0 out of 5 average rating, 28 reviews

Charming Historic Area Retreat!

Welcome to our charming one-bedroom short-term rental nestled in the scenic Lake Morton Historic District and conveniently located near the prestigious Florida Southern College. This thoughtfully designed accommodation offers a perfect blend of modern comfort and historic charm. Situated just a stone's throw away from the beautiful Lake Hollingsworth and Lake Morton our property provides an easy access to leisurely strolls around the lake and jogging trails.

Guest favourite

Guest house in Lakeland

4.96 out of 5 average rating, 49 reviews

Paradise and Palmetto

Located in the charming Lake Morton Historic District on Palmetto Street, this completely detached suite is a five minute walk from so many gems Lakeland has to offer! Located just minutes from downtown, you’ll find many locally owned restaurants, bars and shops. The public library, art museum, Lake Morton and several restaurants are within walking distance from the property. Nearby you’ll also find Florida Southern College and Southeastern University.

Guest favourite

Guest house in Lakeland

4.95 out of 5 average rating, 107 reviews

Hidden Emerald-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 the major cities of Orlando and Tampa for the urban seekers. Reserved guest parking, yard sitting area, washer & dryer, work station, and a children-safe environment. This apartment was designed to accommodate all of your needs.

Guest favourite

Guest house in Lakeland

4.98 out of 5 average rating, 214 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!

Guest favourite

Flat in Lakeland

4.96 out of 5 average rating, 293 reviews

Cottage On Cambridge

This cozy Studio Cottage is located just steps away from Lake Hollingsworth and close to Florida Southern College. It has a private entrance and is separate from our main house. You can enjoy the additional outside living areas on your own screened porch or the courtyard, with landscape lighting, grill & fire pit.

Guest favourite

Flat in Lakeland

4.9 out of 5 average rating, 121 reviews

Adorable 1 bed/1bath with office and free parking

This beautiful duplex is located in a Historic Bungalow built in the late 1920s, centrally located in Lakeland downtown. Nice park across the street for exercising or spending time with kids. Walgreens is one block away, and local bars, restaurants, antique stores, and lots of beautiful historic bungalows