Winter Haven vacation rentals

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Top-rated vacation rentals in Winter Haven

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

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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 !

Jan 18 – 25

G$15,578 GYD per night

Guest favorite

Villa in Lake Wales

4.99 out of 5 average rating, 179 reviews

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

Aug 1 – 8

G$31,890 GYD per night

Guest favorite

Guesthouse in Winter Haven

4.87 out of 5 average rating, 144 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

May 30 – Jun 6

G$15,565 GYD per night

Guest favorite

Apartment in Auburndale

4.95 out of 5 average rating, 215 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

May 31 – Jun 7

G$17,596 GYD per night

Superhost

Guesthouse in Winter Haven

4.87 out of 5 average rating, 233 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 8 – 15

G$17,484 GYD per night

Guest favorite

Guesthouse in Winter Haven

4.84 out of 5 average rating, 147 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!

Jul 31 – Aug 7

G$18,267 GYD per night

Guest favorite

Home in Lake Alfred

5.0 out of 5 average rating, 133 reviews

LA Loft, Upstairs private studio

We are so excited to open our loft for guests. Located conveniently between Tampa and Orlando, you get to experience the best of both worlds in Central Florida. Our home is in a quiet, lakeside neighborhood where guests will have the benefit of a separate entrance to the private and spacious upstairs suite. Our loft is designed to comfortably fit one or two people for the perfect getaway. Come and enjoy the best southern hospitality Central Florida has to offer!

Sep 25 – Oct 2

G$18,410 GYD per night

Guest favorite

Home in Winter Haven

4.96 out of 5 average rating, 270 reviews

Spacious 3 Bed, 2 Bath Home Near Legoland

A gem in the Heart of Winter Haven. This brand new 3 bedroom, 2 bathroom home is fresh, clean and ready for guests. You'll have the entire house to yourself with keyless entry and a private fenced backyard. Walking distance to shopping and restaurants. Take a bike ride or short drive (about 1 mile) downtown to visit Four Purls Yarn Shop, Grove Roots Brewery or fantastic local eateries like Union Taproom, Thai Haven or Arabella's. 4 miles from Legoland.

Jun 27 – Jul 4

G$30,197 GYD per night

Guest favorite

Guest suite in Winter Haven

4.91 out of 5 average rating, 141 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

Aug 19 – 26

G$21,103 GYD per night

Guest favorite

Loft in Auburndale

4.93 out of 5 average rating, 138 reviews

2 Bedroom Apartment near Legoland and Disney

This Private Studio features kitchenette with dining are private bath, private entrance with spectacular lake views over Lake Ariana. This upstairs unique space has private entrance, spectacular lake views from your private Main Studio bedroom with large Balcony. The Kitchenette with dining table is located in between of the 2 Bedrooms. The second Bedroom is only 10'x10' with a Queen and Wardrobe

Aug 7 – 14

G$23,440 GYD per night

Guest favorite

Guesthouse in Auburndale

4.97 out of 5 average rating, 194 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.

Aug 2 – 9

G$15,355 GYD per night

Guest favorite

Guest suite in Winter Haven

4.96 out of 5 average rating, 259 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)

Mar 7 – 14

G$23,790 GYD 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

Superhost

Home in Winter Haven

4.86 out of 5 average rating, 110 reviews

The Flamingo

Oct 5 – 12

G$20,302 GYD per night

Guest favorite

Home in Winter Haven

4.9 out of 5 average rating, 154 reviews

Hidden Haven Lakehouse Pool by Legoland

Sep 25 – Oct 2

G$38,861 GYD per night

Guest favorite

Home in Auburndale

4.95 out of 5 average rating, 137 reviews

three bedroom family house, near legoland

Jun 18 – 25

G$24,454 GYD per night

Guest favorite

Home in Winter Haven

4.98 out of 5 average rating, 99 reviews

Spectacular Waterfront Home in Winter Haven

Jun 24 – Jul 1

G$155,976 GYD per night

Guest favorite

Home in Lakeland

4.96 out of 5 average rating, 116 reviews

Cute, Historic District Home - GREAT LOCATION

Aug 19 – 26

G$27,012 GYD per night

Superhost

Home in Winter Haven

4.89 out of 5 average rating, 261 reviews

The Old Haven - An Enduring Piece of Nostalgia

Jul 24 – 31

G$31,432 GYD per night

Guest favorite

Home in Lakeland

4.9 out of 5 average rating, 381 reviews

Charming guest house

Apr 25 – May 2

G$21,537 GYD 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

Nov 23 – 30

G$27,163 GYD per night

Show all

Other great vacation rentals in Winter Haven

Guest favorite

Guesthouse in Lake Alfred

4.95 out of 5 average rating, 120 reviews

Adorable Agave Suite w/ private pool and entrance

Sep 6 – 13

G$18,573 GYD per night

Guest favorite

Guesthouse in Lake Hamilton

4.9 out of 5 average rating, 146 reviews

Luxury Cottage Near Legoland & Chain of Lakes

Sep 22 – 29

G$28,320 GYD per night

Guest favorite

Cottage in Eagle Lake

4.99 out of 5 average rating, 225 reviews

Central FL Lake House, Sleeps 5, Close to Legoland

Jul 22 – 29

G$38,502 GYD per night

Superhost

Cottage in Winter Haven

4.84 out of 5 average rating, 121 reviews

5 Ships Ahoy Bungalow Unit 17

Nov 15 – 22

G$24,594 GYD per night

Guest favorite

Tiny home in Babson Park

4.91 out of 5 average rating, 294 reviews

Lil cedar tiny home, on crooked lake

Jun 11 – 18

G$22,186 GYD per night

Guest favorite

Cabin in Davenport

4.92 out of 5 average rating, 170 reviews

$89! Cozy Cabin- Disney 20 Miles Away!

Jul 26 – Aug 2

G$22,105 GYD per night

Guest favorite

Cottage in Davenport

4.92 out of 5 average rating, 130 reviews

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

Jul 19 – 26

G$19,726 GYD per night

Guest favorite

Bungalow in Lakeland

4.99 out of 5 average rating, 100 reviews

Charming Bungalow with Front Porch

Oct 10 – 17

G$21,981 GYD 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 Downtown Winter Haven, over 250 vacation rentals in Florence Villa, and over 250 vacation rentals in Eagle Lake.
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 private suite rentals in Winter Haven?
Experience the best of Winter Haven with our private suite rentals, starting at about $40 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 80 homes with self check-in, over 50 homes with a bbq area, over 260 homes with wifi, over 20 homes with a gym, 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 guesthouse rentals in Winter Haven have wifi?
Absolutely! We offer over 20 guesthouse 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 Winter Haven

Home in Winter Haven

Home in Auburndale

Home in Winter Haven

Home in Lakeland

Home in Winter Haven

Home in Lakeland

Home in Haines City

Other great vacation rentals in Winter Haven

Guesthouse in Lake Alfred

Guesthouse in Lake Hamilton

Cottage in Eagle Lake

Cottage in Winter Haven

Tiny home in Babson Park

Cabin in Davenport

Cottage in Davenport

Bungalow in Lakeland

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 private suite 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 guesthouse rentals in Winter Haven have wifi?

Do house rentals in Winter Haven have a gym?

Destinations to explore