Lakeland - Winter Haven Vacation Rentals from CA $57: Short-Term Rentals for 2026

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Our top choices for Lakeland - Winter Haven vacation rentals

A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

1. BlockHaven near Legoland & Disney

Winter Haven

Yuliett

CA $323 total

includes taxes & fees

Nov 12 - Nov 13

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.

2. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Orlando

Bienvenido A

CA $177 total

includes taxes & fees

Nov 29 - Nov 30

A building with a red door, numbered 132C, and a small porch area with a metal stool and a green bucket with a wooden stick.

3. Tiny Paradise

Winter Haven

Cheryl K.

CA $161 total

includes taxes & fees

Nov 11 - Nov 12

A spacious indoor area with a seating area, a counter, and a kitchen visible in the background.

4. Dundee | 2 Queen Bed Nmsk

Dundee FL

Anonymous traveller

CA $139 total

includes taxes & fees

Nov 30 - Dec 1

A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

5. The Russell Lake House

Winter Haven

Jake D.

CA $285 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with a fence, lounge chairs, and a palm tree.

6. Lake Ida Beach Resort

Winter Haven

Heather

CA $105 total

includes taxes & fees

Nov 17 - Nov 18

A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

7. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

winter have

Kyle P.

CA $199 total

includes taxes & fees

Nov 22 - Nov 23

A spacious living area with a dining table, sofas, and a ceiling fan.

8. Family Vacation Home Near Disney With Resort Pool

Orlando

CA $542 total

includes taxes & fees

Dec 2 - Dec 3

A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

9. Vacation Village Orlando, Celebration

Kissimmee

Desiree

CA $154 total

includes taxes & fees

Nov 29 - Nov 30

A lakeside dock with boats, a wooden structure with a metal roof, and dense trees in the background.

10. Camp Mack Lodge, Marina & RV Resort

Lake Wales

Terri

CA $180 total

includes taxes & fees

Nov 11 - Nov 12

A bedroom with a bed, a brown sofa, a ceiling fan, and a green wall with three rectangular mirrors.

11. The Exclusive Tatman Evergreen Suite

Lake Alfred

RaceFan4Life 7.

CA $129 total

includes taxes & fees

Dec 1 - Dec 2

A cozy cabin-style bedroom with a large bed, a sitting area with a couch, and a kitchenette.

12. The Lake Alfred Citrus Wood Guest Cabin

Lake Alfred

Teresa

CA $174 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with wooden cabinets, a dining table with chairs, and pendant lights.

13. Landing Apartments Lakeland Near Winston

Lakeland

Manuel

CA $420 total

includes taxes & fees

Nov 15 - Nov 16

A residential driveway leading to a garage with a white garage door, surrounded by lush greenery and trees.

14. Private Studio Suite

Lakeland

Heather

CA $182 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with stainless steel appliances, a microwave, and a refrigerator.

15. Studio Signature

Lakeland

Juanita

CA $235 total

includes taxes & fees

Nov 15 - Nov 16

A grassy area with a view of the sunset over a body of water, a covered structure, and a palm tree.

16. Cozy 1 Bedroom home on Beautiful Lake Alfred

Lake Alfred

Mike T.

CA $265 total

includes taxes & fees

Nov 15 - Nov 16

A wooden dock leading to a calm lake with a 'NO SWIMMING' sign, surrounded by trees and a clear sky.

17. Grand Lake Resort

Kissimmee

Rose

CA $135 total

includes taxes & fees

Nov 30 - Dec 1

18. Upstay: Stylish 3BR Condo w Pationear Disney

Winter Garden

Ismael

CA $324 total

includes taxes & fees

Nov 30 - Dec 1

A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

19. Lifetime of Vacations Resort

Kissimmee

Alena

CA $142 total

includes taxes & fees

Nov 29 - Nov 30

A hotel room with a bed, a sofa, a bedside table, a mirror, and a window with curtains.

20. Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler

Lakeland Highlands

Casey W.

CA $217 total

includes taxes & fees

Nov 10 - Nov 11

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Find vacation rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

10/10 Excellent

We loved our stay here! The apartment was modern and renovated. It was very roomy too. The beds were comfy, clean and the bedding was excellent quality. Staff were always pleaselant and helpful. The pool was very warm (remember to bring your towels!) The breakfast had lots of variety and was fresh. As a bonus, the coffee was actually good! Laundry on site, which is convenient too. This hotel was a quick drive to legoland and peppa pig theme park. I would definitely stay here again. 10 out of 10...

Emily

A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.

Best Western Plus Winter Haven Inn & Suites

Winter Haven

10/10 Excellent

Rodney

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

10/10 Excellent

Jason N

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

10/10 Excellent

Amber

A hotel entrance with a glass canopy, a reception desk, and a seating area with plants.

Holiday Inn Express & Suites Lakeland South by IHG

Lakeland

10/10 Excellent

Suzana

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Bay Lake

10/10 Excellent

mercy

A spacious lobby with a high ceiling, two exits, and comfortable seating areas with tables and chairs.

Hilton Vacation Club Polynesian Isles Kissimmee

Kissimmee

10/10 Excellent

Ronald

A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

The Berkley, Orlando

Kissimmee

10/10 Excellent

This hotel is amazing - a three bedroom condo with full kitchen, living room and dining room was the perfect solution to two families traveling with an infant! We either cooked or ordered in every night. Tons of storage, great kitchen facilities, dishwasher and jacuzzi to boot. Ashley at the front desk was super helpful. Whenever we had an issue (eg: wheel broke on dishwasher rack) the maintenance guys came super quickly. This hotel honestly cares about your vacation experience and about your...

family w/kids

An outdoor seating area with sofas, chairs, and a fire pit.

Home2 Suites By Hilton Winter Haven

Winter Haven

10/10 Excellent

Kimfa

An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

Staff was amazing. Very clean. Good breakfast options. Would definitely stay here again. Close to stores and food options. Hotel itself was amazing. Only big issue as I was relying on the shuttle services was They definitely need more shuttle options to theme parks. It was booked up everyday as they share the bus with 6 other hotels and can only accommodate 50 passengers. There was limited times for the shuttles as well I wouldn’t rely on the shuttles to get you to theme parks. It was also...

Teena

A resort with multiple swimming pools, a large central pool, and a lake.

Embassy Suites By Hilton Orlando Sunset Walk

Kissimmee

10/10 Excellent

We recently stayed at The Embassy Suites on Sunset Walk and had a fantastic experience. The hotel offers great amenities, including a fitness center, free daily breakfast, and complimentary Wi-Fi. The rooms are spacious and feel luxurious, with modern furnishings and pretty views. Located close to restaurants on Sunset Walk, a water park, and shopping - it's perfect for walking around and exploring the area. The pool area is beautiful, ideal for relaxing, and the hotel staff are incredibly...

Dzenita

A swimming pool with a slide and a small waterfall feature, surrounded by lounge chairs and umbrellas.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

carine

Find out more about Lakeland - Winter Haven

Everything you need to know about Lakeland - Winter Haven vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeland - Winter Haven vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lakeland - Winter Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lakeland - Winter Haven vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lakeland - Winter Haven. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lakeland - Winter Haven vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lakeland - Winter Haven vacation rentals we have selected for you start as low as CA $57 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lakeland - Winter Haven rentals

At Expedia, we put the best Lakeland - Winter Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Lakeland - Winter Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lakeland - Winter Haven vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lakeland - Winter Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Lakeland - Winter Haven Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lakeland - Winter Haven vacation rentals

1. BlockHaven near Legoland & Disney

2. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

3. Tiny Paradise

4. Dundee | 2 Queen Bed Nmsk

5. The Russell Lake House

6. Lake Ida Beach Resort

7. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

8. Family Vacation Home Near Disney With Resort Pool

9. Vacation Village Orlando, Celebration

10. Camp Mack Lodge, Marina & RV Resort

11. The Exclusive Tatman Evergreen Suite

12. The Lake Alfred Citrus Wood Guest Cabin

13. Landing Apartments Lakeland Near Winston

14. Private Studio Suite

15. Studio Signature

16. Cozy 1 Bedroom home on Beautiful Lake Alfred

17. Grand Lake Resort

18. Upstay: Stylish 3BR Condo w Pationear Disney

19. Lifetime of Vacations Resort

20. Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler

Find vacation rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

Staybridge Suites Winter Haven Auburndale by IHG

10/10 Excellent

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven vacation rentals: An excellent choice for every season

How to find incredible deals on Lakeland - Winter Haven rentals

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