Vacation rentals in Lakeland-Winter Haven Metropolitan Area

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

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

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Guest favorite

Guesthouse in Lakeland

4.95 out of 5 average rating, 160 reviews

Swan City Studio +Private Courtyard, pet friendly!

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!

Guest favorite

Home in Lakeland

4.97 out of 5 average rating, 143 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 favorite

Guest suite in Lakeland

4.83 out of 5 average rating, 250 reviews

Cozy Suite in the Heart of Lakeland

This amazing, private suite is located on one of the most desired streets in all of Lakeland, and right near the beautiful Lake Hollingsworth. It is less than a block away from both the lake and Commonground Park. It is located along the I-4 between Tampa (40 min drive) and Orlando/Disney and its attractions (1 hr drive). It has close access to route 98 and the 570 Polk Pkwy and many other attractions, shopping, restaurants, and entertainment. You will love this place!

Guest favorite

Bungalow in Lakeland

4.99 out of 5 average rating, 114 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 favorite

Rental unit in Lakeland

4.88 out of 5 average rating, 282 reviews

2BR/1BA Downtown Cozy Hideaway

This cozy mother in law suite is a duplex that shares a wall with the main house but not an entrance. You will be blocks away from a neighborhood playground as well as beautiful Lake Hollingsworth. Being in the heart of Lakeland, you are never far from entertainment or nature. It's almost equally distant from Orlando and Tampa at about a 45-minute drive and the beach being about an hour and 20 minutes away. All that downtown has to offer is just 2 miles away.

Guest favorite

Bungalow in Lakeland

4.95 out of 5 average rating, 105 reviews

Central Location, Charming Historic Bungalow

Craftsman style bungalow on quiet, cobblestone streets in a beautiful Historic District. Enjoy the neighborhood park, sip a latte at the Hillcrest Coffee Shop, enjoy the birds and wildlife of Lake Hunter or take a short walk to downtown Lakeland with it's many wonderful restaurants, entertainment venues and more beautiful lakes. The RP Funding Center is a 10 minute walk away and the location also provides easy access to I-4 for trips to Tampa or Orlando.

Guest favorite

Guesthouse in Lakeland

4.96 out of 5 average rating, 133 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 favorite

Guesthouse in Lakeland

4.98 out of 5 average rating, 229 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

Guesthouse in Lakeland

4.87 out of 5 average rating, 106 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.

Guest favorite

Home in Lakeland

4.95 out of 5 average rating, 106 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.

Guest favorite

Home in Lakeland

4.91 out of 5 average rating, 426 reviews

Charming guest house

PRIVATE 1 bedroom 1 bath guest house! NO SHARED SPACES. Private patio with HOT TUB all to yourself during your stay! We’re centrally located in Lakeland between Tampa and Orlando. We’re on a nice quiet 1 acre property out in the country but still within 10 minutes of the mall, local parks, stores, and all major restaurants.

Guest favorite

Rental unit in Lakeland

4.91 out of 5 average rating, 149 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