Winter Haven vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Winter Haven

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Winter Haven

4.95 out of 5 average rating, 202 reviews

The Paradise Hide Away

This is a beautiful and private place newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! Talk to me if you need different check in/out times? Dogs are allowed with permission. There is a $200 fully refundable pet security deposit to cover any damages that may occur since Airbnb doesn’t cover damages caused by pets plus a non refundable pet fee of $50 per pet for every 1-7 day period and must be paid before checking in !

Oct 15 – 22

R1,364 ZAR per night

Guest favorite

Guesthouse in Lake Alfred

4.96 out of 5 average rating, 116 reviews

Adorable Agave Suite w/ private pool and entrance

Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your “shome” away from home. Upon entry of the the property you will find a private back entrance, covered parking, private screened in pool and mature trees. Your guesthouse comes equipped with 1 cozy queen size bed, pull-out sofa bed, walk-in shower, kitchenette, smart tv, wifi and more. Looking to explore? We are centrally located to your nearest parks & Florida attractions. Close to fishing docks & bike trails.

Oct 6 – 13

R1,684 ZAR per night

Guest favorite

Guesthouse in Winter Haven

4.87 out of 5 average rating, 143 reviews

Brutus Way Cottage, a cosy hide away

Enjoy a quick get away at Brutus Way Cottage. It is located to the rear of Lili Haven Bed N Breakfast. On your picturesque drive around Lake Howard, with its walking trail, you will take a right onto a quaint curvy lane known as S. Lake Cannon Drive NW . Be my guest at the cottage surrounded by flowers ; the cottage is nestled in the trees to the back past the Iron gates. Use of the Laundry room available upon request. Have a Hallmark Christmas as we decorate with stylish frills and spills

Sep 13 – 20

R1,501 ZAR per night

Guest favorite

Apartment in Auburndale

4.96 out of 5 average rating, 212 reviews

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

Jun 13 – 20

R1,618 ZAR per night

Superhost

Guesthouse in Winter Haven

4.87 out of 5 average rating, 231 reviews

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

Dec 20 – 27

R1,631 ZAR per night

Guest favorite

Guesthouse in Winter Haven

4.84 out of 5 average rating, 145 reviews

Adorable 1 bedroom Guesthouse near Lego Land

This is a beautiful and private place offers a queen size bed, newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! We are located less than 8.6 miles from Legoland & under 6.2 miles from the Lake Myrtle Sports complex. Winter Haven is halfway between Orlando and Tampa. Around 29 miles to Disney World, Universal and Sea World. Around 38 miles to Bush Gardens, Dali museum, Aquarium and much more!

Oct 23 – 30

R1,654 ZAR per night

Guest favorite

Home in Winter Haven

4.94 out of 5 average rating, 141 reviews

Cozy Family Home Near Legoland

Relax with the fam after a fun day at LEGOLAND (4.1 miles) or Disney World (36 miles) in our cozy home complete with a well-stocked kitchen, fully-fenced backyard, and comfortable beds. Spend a day on the famous Chain of Lakes (24 canal-connected lakes), catch a free ski show on Lake Silver, wander downtown to shop, or toast a pint at Union Taproom. Winter Haven is centrally located between Tampa and Orlando with plenty of fun nearby for the whole family.

Jan 18 – 25

R2,584 ZAR per night

Guest favorite

Guest suite in Winter Haven

4.91 out of 5 average rating, 139 reviews

2 Bedroom Winter Haven Guest Suite

Private lock-off unit. Only shared between your party. 1st bedroom -Queen bed and sitting area bathroom attached. 2nd bedroom- two twin sized beds Kitchen and living room included and not shared outside of your party. 3 minutes from Winter Haven hospital. Self check in and out. 20 minutes from Legoland. 45 minutes from Disney and Universal This is an older florida neighborhood with a diverse and working class vibe. Located on Lake Maude

Oct 2 – 9

R1,940 ZAR per night

Superhost

Cottage in Winter Haven

4.84 out of 5 average rating, 120 reviews

5 Ships Ahoy Bungalow Unit 17

Florida’s lakes and biggest attractions are calling you and your family to stay at this vacation rental in Winter Haven! From Legoland and Disney World to the famous Chain of Lakes and golf courses galore, this charming home in Cypress Inlet is minutes from it all. Take your boat out on Lake Eloise, through a private canal right outside the home, or take the kiddos to SeaWorld, a short drive away, before returning to this 2-bedroom 2-bath home.

Nov 15 – 22

R2,261 ZAR per night

Guest favorite

Guesthouse in Auburndale

4.97 out of 5 average rating, 192 reviews

Private Poolside Villa

Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Sep 19 – 26

R1,523 ZAR per night

Guest favorite

Guest suite in Winter Haven

4.96 out of 5 average rating, 256 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. Fishing available on site. New dock just finished with plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door, horse paddocks and patio overlooking the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

Nov 27 – Dec 4

R2,187 ZAR per night

Superhost

Home in Winter Haven

4.86 out of 5 average rating, 110 reviews

The Flamingo

The Flamingo has been completely refreshed with paint, flooring, beds, furniture and many kitchen amenities. It is located 5 miles from Legoland, 30 miles to Disney World, near great restaurants, lakes, downtown Winter Haven and various shopping and attractions.

Mar 19 – 26

R1,869 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winter Haven vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Winter Haven's top sights

LEGOLAND Florida Water Park104 locals recommend

Winter Haven Hospital4 locals recommend

Chain O' Lakes Complex4 locals recommend

Harborside25 locals recommend

Manny's Chophouse- Winter Haven9 locals recommend

Andy's Dine-In Restaurant14 locals recommend

Other great vacation rentals in Winter Haven

Guest favorite

Home in Lake Alfred

5.0 out of 5 average rating, 132 reviews

LA Loft, Upstairs private studio

Aug 23 – 30

R1,693 ZAR per night

Superhost

Home in Winter Haven

4.9 out of 5 average rating, 259 reviews

The Old Haven - An Enduring Piece of Nostalgia

Aug 4 – 11

R2,827 ZAR per night

Guest favorite

Home in Winter Haven

4.9 out of 5 average rating, 152 reviews

Hidden Haven Lakehouse Pool by Legoland

Jul 9 – 16

R3,759 ZAR per night

Guest favorite

Home in Haines City

4.88 out of 5 average rating, 136 reviews

3 Bedroom Executive with Private Pool near Disney

Oct 20 – 27

R2,497 ZAR per night

Guest favorite

Home in Lakeland

4.91 out of 5 average rating, 378 reviews

Charming guest house

Jul 3 – 10

R1,980 ZAR per night

Guest favorite

Home in Auburndale

4.95 out of 5 average rating, 136 reviews

three bedroom family house, near legoland

Jun 26 – Jul 3

R2,483 ZAR per night

Guest favorite

Home in Winter Haven

4.89 out of 5 average rating, 36 reviews

Newly remodeled House 3BR/2BA

Oct 25 – Nov 1

R1,945 ZAR per night

Guest favorite

Home in Winter Haven

4.97 out of 5 average rating, 63 reviews

The Dalt Retreat

Sep 14 – 21

R2,345 ZAR per night

Show all

Other great vacation rentals in Winter Haven

Guest favorite

Villa in Lake Wales

4.99 out of 5 average rating, 179 reviews

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

Jul 26 – Aug 2

R2,932 ZAR per night

Guest favorite

Guesthouse in Lake Hamilton

4.9 out of 5 average rating, 142 reviews

Luxury Cottage Near Legoland & Chain of Lakes

Jul 25 – Aug 1

R2,716 ZAR per night

Guest favorite

Cottage in Davenport

4.92 out of 5 average rating, 127 reviews

$79! Cozy Cottage + Outdoor Fun -Close to Disney!

Jun 5 – 12

R1,814 ZAR per night

Guest favorite

Loft in Auburndale

4.94 out of 5 average rating, 135 reviews

2 Bedroom Apartment near Legoland and Disney

Aug 24 – 31

R2,180 ZAR per night

Guest favorite

Guesthouse in Winter Haven

4.91 out of 5 average rating, 54 reviews

Comfy Guest House

Aug 29 – Sep 5

R1,858 ZAR per night

Guest favorite

Guest suite in Winter Haven

4.86 out of 5 average rating, 73 reviews

Cute & Cozy Guesthouse in Winter Haven

Mar 22 – 29

R1,550 ZAR per night

Guest favorite

Tiny home in Winter Haven

4.95 out of 5 average rating, 20 reviews

Tiny home in Winter Haven hosted by Bob & Susana

Jun 28 – Jul 5

R1,769 ZAR per night

Guest favorite

Guesthouse in Auburndale

4.98 out of 5 average rating, 94 reviews

Cozy 2-bedroom guesthouse on the lake

Dec 11 – 18

R2,205 ZAR per night

Show all

Quick stats about vacation rentals in Winter Haven

Total rentals
370 properties
Rentals with dedicated workspaces
210 properties have a dedicated workspace
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
210 properties are a good fit for families
Total number of reviews
14K reviews

Frequently Asked Questions

Where should I stay in Winter Haven?
Make yourself at home in Winter Haven by choosing from our most frequently booked neighborhoods. We have over 250 vacation rentals in Florence Villa, over 250 vacation rentals in Eagle Lake, and over 250 vacation rentals in Downtown Winter Haven.
Are there vacation rentals with a dedicated workspace in Winter Haven?
Yes! Work meets play with ease at over 210 vacation rentals in Winter Haven featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winter Haven?
Four-legged friends are welcome in Winter Haven. Choose from more than 110 vacation rentals for guests traveling with pets.
Are there Winter Haven vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 80 vacation homes with pools in Winter Haven, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in apartment rentals in Winter Haven?
Experience the best of Winter Haven with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Winter Haven?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with a bbq area, over 260 homes with wifi, over 20 homes with a gym, over 80 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Winter Haven?
Winter Haven has more than 210 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winter Haven have a bbq area?
Absolutely! We offer over 50 house rentals with a bbq area in Winter Haven. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Winter Haven have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Winter Haven. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Haven have a gym?
Absolutely! We offer over 20 house rentals with a gym in Winter Haven. Enjoy a tailored experience with all the comforts you desire.

Winter Haven vacation rentals

Top-rated vacation rentals in Winter Haven

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Winter Haven vacation rentals

Stay near Winter Haven's top sights

Other great vacation rentals in Winter Haven

Home in Lake Alfred

Home in Winter Haven

Home in Winter Haven

Home in Haines City

Home in Lakeland

Home in Auburndale

Home in Winter Haven

Home in Winter Haven

Other great vacation rentals in Winter Haven

Villa in Lake Wales

Guesthouse in Lake Hamilton

Cottage in Davenport

Loft in Auburndale

Guesthouse in Winter Haven

Guest suite in Winter Haven

Tiny home in Winter Haven

Guesthouse in Auburndale

Quick stats about vacation rentals in Winter Haven

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Winter Haven?

Are there vacation rentals with a dedicated workspace in Winter Haven?

Are there pet-friendly vacation rentals in Winter Haven?

Are there Winter Haven vacation rentals on Airbnb with pools?

How much does it cost to stay in apartment rentals in Winter Haven?

What are the most popular amenities for House Rentals in Winter Haven?

Are there family-friendly vacation rentals in Winter Haven?

Do house rentals in Winter Haven have a bbq area?

Do cottage rentals in Winter Haven have wifi?

Do house rentals in Winter Haven have a gym?

Destinations to explore