Beginning of main content

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Featured Cottages in Winter Haven

$79
Lake Ida Beach Resort

Lake Ida Beach Resort

3.0 out of 5.0 2524 Lake Alfred Rd, Winter Haven, FL
5/5
(1 Reviews)
An outdoor pool, free self parking, and laundry facilities are featured at this cottage. WiFi in public areas is free. A terrace, a picnic area, and barbecue grills are also on offer.
 
$68
One Bedroom Studio Suite Cottage in Beautiful Country Setting

One Bedroom Studio Suite Cottage in Beautiful Country Setting

Plant City, FL
A garden is available at this cottage.
 
Get Rates
5 Star Private Apartment, Reunion Resort and Spa, Orlando Apartment 2781

5 Star Private Apartment, Reunion Resort and Spa, Orlando Apartment 2781

7516 Gathering Drive, Kissimmee, FL
A restaurant and a poolside bar are featured at this cottage. Free self parking, a terrace, and WiFi in public areas are also offered.
 
Get Rates
Private Cottage 10 Minutes To Disney And 15 To Universal! Resort Style!

Private Cottage 10 Minutes To Disney And 15 To Universal! Resort Style!

Kissimmee, FL
A fitness center is available at this cottage.
 
Get Rates
Family Villa Close to Lake, Near Disney - 6av390

Family Villa Close to Lake, Near Disney - 6av390

390 Miro Drive, Davenport, FL
This cottage features an outdoor pool and a fitness center. Families will appreciate the arcade/game room and picnic area. Enjoy the spa tub and perks like free self parking and free WiFi.
 
Get Rates
Solterra Resort - Brand NEW 5bed Pool Home #5st417

Solterra Resort - Brand NEW 5bed Pool Home #5st417

3.5 out of 5.0 5417 Misty Oak Circle, Davenport, FL
This cottage features an outdoor pool and a fitness center. Business travelers can take advantage of the free WiFi in public areas. Free self parking and a garden are also offered on site.
 
Get Rates
Regal Palms - Spacious 4bed Town House #4rp908

Regal Palms - Spacious 4bed Town House #4rp908

3.5 out of 5.0 3908 Calabria Avenue, Davenport, FL
This cottage features an outdoor pool and a fitness center. Business travelers can take advantage of the free WiFi in public areas. Enjoy the spa tub and perks like free self parking.
 
Get Rates
Hampton Lakes - Lovely 3bd/2ba Pool Home 3hl905

Hampton Lakes - Lovely 3bd/2ba Pool Home 3hl905

3.5 out of 5.0 905 Lockbreeze Drive, Davenport, FL
An outdoor pool is featured at this cottage, along with free self parking. WiFi in public areas is free. WiFi in public areas is also provided.
 
Get Rates
Greater Groves - 5 Bedrooms House w/pool-5202GG

Greater Groves - 5 Bedrooms House w/pool-5202GG

3.5 out of 5.0 1607 Nectarine Trail, Clermont, FL
An outdoor pool is featured at this cottage, along with free WiFi in public areas and barbecue grills.
 
$144
Lakeland s Luxury Cottage Retreat

Lakeland s Luxury Cottage Retreat

Lakeland, FL
A garden is available at this cottage.
 
Get Rates
Solterra Resort - Lovely 5bd/4ba Pool Home #5st429

Solterra Resort - Lovely 5bd/4ba Pool Home #5st429

3.5 out of 5.0 5429 Misty Oak Circle, Davenport, FL
This cottage features an outdoor pool and a fitness center. Business travelers can take advantage of the free WiFi in public areas. Free self parking and a garden are also offered on site.
 
Get Rates
Aviana Resort - Beautiful 4bd/3ba Villa - #4940

Aviana Resort - Beautiful 4bd/3ba Villa - #4940

3.5 out of 5.0 326 Paloma Drive, Davenport, FL
This cottage features an outdoor pool and a fitness center. Families will appreciate the arcade/game room and picnic area. Enjoy the spa tub and perks like free self parking and free WiFi.
 
Map

Winter Haven Cottages For Rent

Dreaming of a getaway that’s reminiscent of a fairytale? Travelocity doesn’t have magic wands or talking animals in our inventory—at least, none that we can find—but we do have holiday cottages in Winter Haven that will make you feel like you’ve stepped inside your vacation dreams.

The word “cottage” may make you think of whitewashed walls, flower print curtains, and sprawling views of rolling green hills—lucky for you, we do offer tons of country cottages that were furnished with a rustic feel in mind. Appreciate the vase of daffodils on your dining room table, and peek out the window onto the private patio that surrounds yours and other rustic cottages in the area.

These charming “home away from homes” have long been a beacon for those who love the outdoors, so pick a spot peppered with hiking trails and spend lazy afternoons meandering through the gorgeous scenery Winter Haven is known for. Snap some pictures while you’re at it—you’ll want to remember sunset over this waterfall for the rest of your life. When the sun goes down, cuddle up in front of a cheerful fire, or head into town to explore the shops, restaurants, and art galleries that have sprung up over the years. Ah, it’s nice to return to civilization every once in a while, isn’t it?

Whether you select cottages minutes away from the bustling city center, or coastal cottages that are footsteps from the sand and surf, you’ll find the accommodation you’re looking for here on Travelocity. Just because you’re booking a place that reminds you of a fairytale doesn’t mean you need a fairy godmother to find the best deal around! Just a gnome…

What is the price range for Cottages in Winter Haven?

We have up to a variety of Cottages available in Winter Haven, ranging from $68 to $161.

How many options are there for Cottages in Winter Haven?

Book your stay in Winter Haven Cottages through Travelocity today and choose from 34874 available options.

How cheap are Cottages in Winter Haven?

Travelers to Winter Haven can find Cottages priced as low as $68.

Top Trending Hotels in Winter Haven

See all 34,874 Properties in Winter Haven
Winter Haven Gardens Inn and Banquet Center $69
Winter Haven Gardens Inn and Banquet Center

Winter Haven Gardens Inn and Banquet Center

1150 3rd Street SW, Winter Haven, FL
     
    2.5 out of 5.0 Stars

    Situated in Winter Haven, this hotel is within 1 mi (2 km) of Indigo's Family Fun Center and Chain of Lakes Park. Lake Conine is 2.8 mi (4.6 km) away. Winter Haven Station is 16 minutes by foot.

    Howard Johnson by Wyndham Winter Haven FL $81
    Howard Johnson by Wyndham Winter Haven FL

    Howard Johnson by Wyndham Winter Haven FL

    1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
       
      2.0 out of 5.0 Stars

      Situated in the business district, this motel is within a 15-minute walk of Indigo's Family Fun Center and Chain of Lakes Park. Lake Conine is 2.9 mi (4.7 km) away. Winter Haven Station is 14 minutes by foot.

      Econo Lodge $71
      Econo Lodge

      Econo Lodge

      5665 Cypress Gardens Boulevard, Building b, Winter Haven, FL
         
        2.0 out of 5.0 Stars

        Situated in Winter Haven, this hotel is 0.4 mi (0.6 km) from Legoland Florida and within 6 mi (10 km) of Chain of Lakes Park and Indigo's Family Fun Center. Cypresswood Golf and Country Club and Eagle Ridge Mall are also within 9 mi (15 km).

        Courtyard by Marriott Winter Haven $161
        Courtyard by Marriott Winter Haven

        Courtyard by Marriott Winter Haven

        6225 Cypress Gardens Boulevard SE, Winter Haven, FL
           
          3.0 out of 5.0 Stars

          Situated in Winter Haven, this hotel is 0.8 mi (1.2 km) from Legoland Florida and within 6 mi (10 km) of Chain of Lakes Park and Indigo's Family Fun Center. Eagle Ridge Mall and Cypresswood Golf and Country Club are also within 9 mi (15 km).

          Popular Accommodation Searches

          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.