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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Lakeland - Winter Haven cottages

House (3 Bedrooms) | Interior

Explore & Relax: Chic & Cozy Retreat in Lakeland!

Explore & Relax: Chic & Cozy Retreat in Lakeland!
3.0 star property
Lakeland
10.0 out of 10, Exceptional, (1 review)
"We had a great time. The house was beautiful. Decor was beautiful and bedding comforting. I sleep so good. The house was family friendly and plenty of rooms. "
United States
Debra
Explore & Relax: Chic & Cozy Retreat in Lakeland!
Porch

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (193 reviews)
"Was probably once a great time place. Owner was nice. Night time neighborhood is a bit noisy guess it's just how people act now no respect for property."
United States
wade
The price is €76
includes taxes & fees
9 Jun - 10 Jun
Lake Ida Beach Resort
House (4 Bedrooms) | Interior

Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
Family Resort Home w Pool, BBQ & Game Room
Interior

This old Florida feeling getaway is 420 friendly and a great place to just relax

This old Florida feeling getaway is 420 friendly and a great place to just relax
Avon Park
7.4 out of 10, Good, (3 reviews)
"We loved our stay at Kellie’s farm, the property is big and has a big pond or little lake at the back, the scenery looks like you’re somewhere in the wild side of Montana and feels like a grizzly bear can come out of the trees at any moment! Haha but it’s very safe, nothing to worry about. The farm has chickens, pigs, a calf, dogs, etc. if you love animals you will love this place for sure! We would definitely come back and we 100% recommend this place."
United States
Steve M.
This old Florida feeling getaway is 420 friendly and a great place to just relax
Exterior

The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland

The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland
East Lake Morton
The price is €74
includes taxes & fees
16 Jun - 17 Jun
The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland
House (3 Bedrooms) | Interior

Oasis Near Disney w Golf View, Family&pet Friendly

Oasis Near Disney w Golf View, Family&pet Friendly
3.0 star property
Reunion
The price is €321
includes taxes & fees
29 May - 30 May
Oasis Near Disney w Golf View, Family&pet Friendly
Exterior

Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (2 reviews)
"Stay was amazing. Host was very friendly and very easy to communicate with. 10/10 recommend"
United States
Joseph B.
The price is €177
includes taxes & fees
31 May - 1 Jun
Charming Historic Cottage with Cozy Porch and Garden Retreat
Exterior

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
8.8 out of 10, Excellent, (5 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is €241
includes taxes & fees
31 May - 1 Jun
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Exterior

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is €168
includes taxes & fees
31 May - 1 Jun
Perfect Place for a Perfect Vacation
Smart TV, books

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is €182
includes taxes & fees
3 Jun - 4 Jun
Family-Friendly Cottage Near Orlando’s Top Attractions
Interior

Luxe Davenport Duplex w/ Private Pool & Spa

Luxe Davenport Duplex w/ Private Pool & Spa
3.0 star property
Loma Linda
The price is €506
includes taxes & fees
10 Jun - 11 Jun
Luxe Davenport Duplex w/ Private Pool & Spa
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (7 reviews)
"Nice, Cute little place"
United States
Brenda N.
The price is €153
includes taxes & fees
5 Jun - 6 Jun
Tiny house close to Disney KISSIMMEE
House (3 Bedrooms) | Interior

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is €234
includes taxes & fees
2 Jun - 3 Jun
Upstay: Bright Family-friendly Retreat With Patio
Exterior

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is €257
includes taxes & fees
10 Jun - 11 Jun
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Dining

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
The price is €192
includes taxes & fees
13 Jun - 14 Jun
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
House (3 Bedrooms) | Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
Serenity - Family & Pet Friendly, Amazing Location
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (10 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is €239
includes taxes & fees
8 Jun - 9 Jun
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Davenport
5.0 out of 10, (2 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is €138
includes taxes & fees
29 May - 30 May
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Interior

1674 Moon Valley DR, Davenport, 6bed

1674 Moon Valley DR, Davenport, 6bed
2.0 star property
Champions Gate
1674 Moon Valley DR, Davenport, 6bed
House (3 Bedrooms) | Front of property

Orlando Theme Park Basecamp: Family Home w/ Patio

Orlando Theme Park Basecamp: Family Home w/ Patio
3.0 star property
Davenport
The price is €313
includes taxes & fees
29 May - 30 May
Orlando Theme Park Basecamp: Family Home w/ Patio
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Lakeland - Winter Haven Hotel Reviews

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent
"We loved the hotel! The rooms were super clean, and the kitchen had everything needed if you want to cook. We really enjoyed the H2O water park, and the shuttle service to the park was very efficient. Staff super friendly! We will definitely be coming back to this hotel!"
Heidy Hernandez 2-night trip
Posted 9 hours ago
Embassy Suites By Hilton Orlando Sunset Walk

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
226
Accommodation
33 Cottages
Lowest Price
€74
Highest Price
€468

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between €74 and €468 per night. These properties offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Lakeland - Winter Haven?
Choose from 33 cottages in Lakeland - Winter Haven. Whether you're travelling with the whole family, as a twosome or with a group of besties, Expedia can help you secure your perfect fit.
Why book your cottage in Lakeland - Winter Haven with Expedia?
Reserving a cottage in Lakeland - Winter Haven is as simple as entering your travel dates and choosing an ideal place for outdoor relaxation and recreation. From chic retreats to inexpensive properties and cottages that offer conveniences like a kitchen, Expedia has something for all traveller styles. As for irresistible deals? We've got you covered!
How can I find cheap cottages in Lakeland - Winter Haven?
Expedia can help you locate cheap cottages in Lakeland - Winter Haven. To reserve your perfect stay in just a few clicks, use our convenient filter tool to refine your search results by amenities, budget and star rating.
What is there to do in Lakeland - Winter Haven near my cottage?
One of the best travel accessories for your Lakeland - Winter Haven adventure is an awesome itinerary! Polk Museum of Art, RP Funding Centre and Publix Field at Joker Marchant Stadium are among the leading sights if you're off to Lakeland. Winter Haven also lures travellers with its wonderful attractions, such as Indigo's Family Fun Centre. Eager to add to your to-do list? Drop by Chain of Lakes Park and Theatre Winter Haven too.

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