Holiday houses in Lakeland-Winter Haven Metropolitan Area

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

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

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Guest favourite

Home in Lakeland

5.0 out of 5 average rating, 20 reviews

Modern 2 Queens-Walk to Downtown

You will enjoy easy access to everything from this centrally located place. Fully remodeled. Queen beds, comfortable mattresses, in unit washer/dryer. Kitchen is large. Blinds are all double blinds to allow light in when you want it. Blackout shades in the bedroom. We have stocked the unit with everything we can think of! Keurig coffee maker, with pods. Pots, pans, dishes, utensils, kettle. Cooking spices, sugar, flour. Bathroom supplies! Walking distance to dowtown, library, and coffee house.

12 – 19 June

$1,312 AUD total

Guest favourite

Townhouse in Lakeland

4.95 out of 5 average rating, 181 reviews

Glam Townhouse in Downtown Lakeland - 2bed/2bath

Location, Comfort, and Privacy! We have all you look for one night or extended stay. This apartment was newly remodeled and designed for you to feel like home. Private garage, lock code system (key-less). Walking distance from Lake Hollingsworth, Morton, local coffee shops, restaurants, gas stations, etc. Lakeland is also conveniently located between Orlando and Tampa. 40minutes from Disney & Bush Gardens, 30min to Legoland, 1 hour from Orlando/Universal, and the gorgeous beaches on the gulf.

19 – 26 June

$1,556 AUD total

Guest favourite

Home in Lakeland

4.96 out of 5 average rating, 116 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!

19 – 26 Aug

$1,616 AUD total

Guest favourite

Apartment in Lakeland

5.0 out of 5 average rating, 21 reviews

Historic 1920s Carriage House- (Upstairs)

Welcome to Historic Dixieland! This special place is close to everything, making it easy to plan your visit. Feel like home comfort, this space is nicely updated and lacks for nothing! This unique place is 4 min to Downtown Lakeland, 5 min to the RP Funding Center, 45 min to theme parks, and centrally located to all Lakeland has to offer. We also have many restaurants, bars, walking paths, and photo opportunities within walking distance. We hope you choose us for your time in Lakeland!

9 – 16 Aug

$1,382 AUD total

Guest favourite

Apartment in Lakeland

5.0 out of 5 average rating, 23 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!

3 – 10 July

$1,574 AUD total

Guest favourite

Guesthouse in Lakeland

4.94 out of 5 average rating, 145 reviews

Modern Studio + Secluded Courtyard, SEU, FSC,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!

30 May – 6 June

$1,301 AUD total

Guest favourite

Guest suite in Lakeland

4.82 out of 5 average rating, 210 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!

28 July – 4 Aug

$1,129 AUD total

Guest favourite

Bungalow in Lakeland

4.99 out of 5 average rating, 100 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.

5 – 12 Aug

$1,336 AUD total

Guest favourite

Home in Lakeland

4.89 out of 5 average rating, 63 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.

17 – 24 Aug

$1,127 AUD total

Guest favourite

Home in Lakeland

5.0 out of 5 average rating, 27 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.

24 – 31 Aug

$1,029 AUD total

Guest favourite

Guesthouse 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!

13 – 20 Aug

$1,397 AUD total

Guest favourite

Home in Lakeland

4.9 out of 5 average rating, 380 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.

16 – 23 Feb

$1,260 AUD total