Cottage holiday rentals in Winter Haven

An aerial view of the pool area features two pools surrounded by lush greenery and palm trees. The shallow pool has a unique shape with lounging areas, while the larger pool offers numerous sunbed arrangements. Gazebos are visible near the water's edge.

4.96 out of 5 average rating, 206 reviews

Magical Family Escape | Disney | Epic Universe

Welcome to our 2/2 PET FRIENDLY villa just 8 minutes to Disney! Nearby you will find Lake Buena Vista Outlets, Universal Studios, Disney Springs, Old Town, restaurants and more! Stay includes: Disney Costumes Wi-Fi Washer/Dryer Free Parking Access to shuttle to Disney 4 pools including kids area/Calypso Cay Pools withTiki Bar 24 HR Gym, Volleyball/Basketball Court Mini Putt Putt Kids items available upon request. Strollers, etc. Small Pet Fee added for fur friends with complimentary pet food.

4.93 out of 5 average rating, 341 reviews

Entire Cottage for 4 Near Disney - Bitty Bliss

Welcome to Bitty Bliss, your cozy Tiny Cottage escape! Located just 20 minutes from Disney and Universal, with shopping and restaurants only 5 minutes away, it's perfect for relaxation and adventure. Enjoy fantastic amenities like pickleball, mini golf, a new gym, and a rec room—all smoke-free pet-free, and hassle-free with no resort or parking fees! Sleep comfy in the one-bedroom queen bed or the super cozy sleeper sofa, accommodating up to four guests. Charm, comfort, and fun all in one place

4.97 out of 5 average rating, 151 reviews

An inviting living area features a comfortable tufted chaise lounge and a cozy recliner. A flat-screen TV is mounted above a classic fireplace, surrounded by soft curtains that frame bright windows. The floor showcases warm wooden tones, contributing to a homely ambiance.

Cottage in Lake Wales

Charming, renovated 1917 Cottage

Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!

4.85 out of 5 average rating, 233 reviews

A charming cottage exterior is showcased, featuring a combination of white siding and brick accents. Lush greenery surrounds the entrance, while a stone wall and gate provide access. Large front windows invite natural light, offering a welcoming view of the home.

Cottage in Polk City

Cozy Historical Cottage

This lovely cottage of 1,000 sqft of living space, two bedrooms, one bath, dining room. Enjoy the view from the patio overlooking the backyard or relax in the Florida room on a traditional swing. The Van Fleet Trail and Freedom Park are just a few yards away. Popular attractions like Fantasy of Flight, Dinosaur World, Lego Land, and Disney are nearby. The Lakeland Mall is 10 minutes away movies & restaurants. Just a short walk away you'll find two family restaurants. Book your stay today!

An open living space showcases a comfortable sofa and a TV facing the kitchen area, which features modern appliances. Bright yellow curtains complement the neutral decor. A dining table with chairs and a small vase of flowers is visible, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 185 reviews

Modern Cottage Near Disney World | Top Rated

Our cozy, modern vacation cottage is tucked away in a quiet, private community just 4 miles from Walt Disney World and close to everything Orlando has to offer. Highly rated by past guests, (nearly 200 five star reviews) it’s known for its cleanliness, comfort, and thoughtful details. The cottage features a queen bedroom, comfortable living area, full bath, and a fully stocked kitchen with new appliances—an inviting, reliable home base to enjoy the magic and sunshine of Central Florida.

A charming two-story cottage is set within a vibrant neighborhood, featuring a pastel green exterior and a welcoming balcony. Lush palm trees line the front, while well-maintained landscape provides an inviting approach to the entrance. Additional colorful homes can be seen in the background.

4.98 out of 5 average rating, 168 reviews

Margaritaville cottage minutes from Disney

Gorgeous 2 bedroom/2bath cottage located in gated Margaritaville Resort just 6 miles from the Magic Kingdom. This immaculate cottage sleeps six people and has everything you will need to enjoy your vacation. Sunset Walk is an easy 10 minute stroll with plenty of shopping and unique restaurants to choose from. Orlando's newest waterpark, Island H2O Live, is right next to Sunset Walk to enjoy on a hot day. It's time to waste away in Margaritaville, and come enjoy a little "Peace of Paradise".

An outdoor patio features a glass-top table surrounded by six black mesh chairs. A small wooden shed is visible in the background, while a stone pathway leads through the well-maintained yard, enclosed by a wooden fence and dotted with greenery.

4.8 out of 5 average rating, 218 reviews

Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn

This delightful lake-life inspired cottage includes 2 bedrooms and 1 ½ baths, a fooseball table, and easily sleeps 7 guests comfortably. Located just 15 minutes from Legoland and 45 minutes from Tampa & Orlando, this home is perfect for both families and those traveling for work. In fact, this Home is centrally located to dining, shopping, and small town fare. Come stay and enjoy downtown entertainment within walking distance (0.5 miles), or a quick car drive to Legoland (5.2 miles).

4.9 out of 5 average rating, 129 reviews

A cozy living area features two leather sofas positioned around a wooden coffee table with a glass top. In the background, a well-equipped kitchen with wooden cabinetry is visible. Natural light fills the space, enhancing the warm tones of the decor.

Cottage in Lake Wales

The "Little ‘Toa" Ideal for short & long stays!

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

A living area features a light-colored sofa with accent pillows, complemented by a circular coffee table. A patterned rug in shades of red and beige adds warmth. Natural light enters through two windows with yellow curtains, and a front door is prominently displayed.

4.97 out of 5 average rating, 136 reviews

Cozy Orlando Area Cottage - 4 Miles to Disney

With Disney, popular attractions, restaurants, shops, and famous southern sunshine just minutes from your doorstep, we welcome guests to our cozy cottage for your vacation getaway. Our 1 bedroom, 1 bath cottage boasts modern amenities and entertainment options to help you relax during your stay. The cottage is located in a quiet, gated, resort community. Community amenities include an outdoor pool, hot tub, mini golf, game room, fitness center, planned activities, and tennis court.

A charming white cottage is framed by a well-kept lawn, with a brick chimney visible on one side. Lush green shrubs and trees provide shade around the property, and a pathway leads to the entrance, suggesting easy access to the home.

4.99 out of 5 average rating, 113 reviews

Classic Cottage in country setting

Relax with the family in this peaceful setting. Short drive to the parks, shopping, restaurants. 10 minutes from Interstate 4. Walmart and Posner Park Shopping Center nearby. Patio area with fire pit and gas grill and lawn chairs. 2 car carport parking on premise. 2 bedroom w/HDTV's, 2 bath, fully furnished kitchen, dishwasher, breakfast nook, dining room, living room w/HDTV. Washer/dryer. Fully fenced 3/4 acre yard with plenty of room for kids to play. Self check in with keypad.

4.99 out of 5 average rating, 287 reviews

A view of the blue lake house is presented with a well-manicured lawn leading up to it. The house is framed by mature trees, providing shade. A wooden walkway extends toward the entrance, while the serene lake is visible in the background.

Cottage in Eagle Lake

Roe Family Lake House (Lake Mcleod)

We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the kayaks we provide on site!

A round table is placed beneath a colorful, multi-striped umbrella, providing shade. Two chairs with patterned cushions are arranged around the table. A green hose is visible on the side of the tiny home, enhancing the outdoor space.

4.83 out of 5 average rating, 109 reviews

*Tiny Home - New Year Special! resort fees waved!

Private tiny home just for you! Centrally located 1/2 mile from Florida's Turnpike, and 20-25 minutes from Epic Universe, Disney, SeaWorld, Universal, and the Orlando International Airport! The tiny home sleeps two comfortably, but has two twin air mattresses for extra guests. The tiny home is located in a friendly, quiet community with a swimming pool, rec room, fitness center, playground, putting green, shuffleboard and pickle ball court. We look forward hosting you!!

Popular amenities for cottage rentals in Winter Haven

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A cozy living area features a light-colored sofa with coordinating cushions, positioned beside large windows that allow natural light to flood in. A colorful area rug depicting Mickey Mouse adds playfulness, while a glass coffee table sits in front. An open kitchen area is visible in the background.

4.95 out of 5 average rating, 22 reviews

Mickey's Hideaway Cottage - 5 miles from Disney!

A single-story park model home is shown, featuring a stone-accented exterior. A large tree provides shade, while a shed stands nearby. The driveway is paved, and bright greenery surrounds the property, contributing to a welcoming environment.

4.74 out of 5 average rating, 155 reviews

Sherwood Forest Vacation Home Near Disney

4.93 out of 5 average rating, 43 reviews

A charming resort cottage is presented, framed by lush green palms and well-maintained landscaping. The cottage features a covered porch with seating, set against a backdrop of a gray exterior and a metal roof. A tiki hut can be seen to the side, enhancing the tropical feel.

Cottage in Polk City

Paradise Cottage & Tiki Hut at Bay Lake Resort

A spacious deck is furnished with comfortable seating, including two armchairs and a glass-top table. The serene view overlooks a tranquil body of water surrounded by lush greenery and trees, creating a peaceful outdoor gathering space.

4.63 out of 5 average rating, 174 reviews

Sunset Lake House

A red sofa with decorative cushions is positioned against a wall of large windows, allowing natural light to fill the space. A small dining table and various indoor plants are visible, enhancing the cozy atmosphere of the living area.

4.9 out of 5 average rating, 39 reviews

Sherwood - Disney Get'A'Way

4.84 out of 5 average rating, 19 reviews

Cozy Tiny Home Getaway minutes from Disney

A bright, airy living area is showcased with large windows covered by sheer curtains. A cozy sectional couch is paired with a circular table, accented by a patterned rug. Decorative plants and vibrant yellow textiles add warmth to the space, creating a comfortable atmosphere.

4.84 out of 5 average rating, 299 reviews

Private Cottage. Only 5 miles from Disney.

4.82 out of 5 average rating, 105 reviews

Chic Cottage near Disney - Lots of Amenities!

Pet-friendly cottage rentals

A charming blue cottage is depicted, showcasing a combination of large windows and decorative greenery. The entrance is framed by a small garden, with a stone border and a variety of plants, creating an inviting outdoor space. A covered porch area is also visible.

4.88 out of 5 average rating, 225 reviews

Cozy Private Cottage 5 miles from Disney!

A vibrant yellow cottage is framed by tropical landscaping, featuring palm trees and lush green plants. Bright blue accents complement the exterior, which is highlighted by large windows and an inviting porch area. A well-maintained pathway leads to the front door, enhancing the welcoming feel.

4.97 out of 5 average rating, 58 reviews

2BD Cottage in Margaritaville w Playground in back

The exterior view showcases two cottages side by side, featuring porches with railings. The light yellow cottage has steps leading to its entrance. Lush greenery and a paved driveway enhance the surroundings, while a serene body of water can be seen in the background.

4.86 out of 5 average rating, 7 reviews

Charming Cottage #1

4.94 out of 5 average rating, 95 reviews

A charming two-story cottage is depicted, featuring light blue siding and vibrant blue shutters. The entrance is framed by palm trees and lush greenery. A concrete pathway leads to the front door, providing a welcoming entryway to the home.

Cottage in Four Corners

2BD Cottage in Margaritaville Resort near Disney

A hot tub is situated on a patio with a view of a lake at sunset. The vibrant sky features hues of orange, pink, and purple, while a railing surrounds the space, enhancing the scenic atmosphere. The tranquil water reflects the colors of the sky.

4.99 out of 5 average rating, 90 reviews

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

A spacious living room features a comfortable sofa and reclining armchair, complemented by a wooden coffee table. A large television is positioned on a dark wood cabinet. Glass doors lead to an outdoor deck, allowing natural light to fill the space.

4.85 out of 5 average rating, 125 reviews

7 - Country Cottage 2bed/1bath - Unit 9

4.61 out of 5 average rating, 67 reviews

Entire house Close to Disney

The entrance features wooden steps leading up to a covered porch, flanked by tropical foliage. Two chairs are positioned on the porch, offering a place to relax. The home’s exterior is painted in soft green, complemented by light-colored trim.

4.85 out of 5 average rating, 149 reviews

5 - Life's a Beach Retreat 1bed/1bath - Unit 13

Private cottage rentals

The exterior of the cottage is surrounded by lush greenery and decorative plants. A covered porch provides outdoor seating, while the building's light-colored siding complements the blue sky and scattered clouds above.

4.7 out of 5 average rating, 44 reviews

The Cozy Porch

Cottage in Auburndale

New place to stay

Peaceful Boho Lakefront Cottage | Still Waters

A modern vacation rental home is highlighted, featuring a charming exterior with a covered porch and white railings. Lush greenery surrounds the property, and two palm trees are visible, providing a tropical touch. A gravel pathway leads towards the entrance, creating an inviting approach.

4.81 out of 5 average rating, 161 reviews

6 - Just Beachin' Cabin 2bed/2bath - Unit 10

Cottage in Lakeland

Lakeland Cottage w/ Pool Access + Screened Porch!

The cottage exterior is characterized by light-colored siding and charming architectural features. Lush greenery lines the front, with palm trees and colorful plants providing a tropical backdrop. A paved walkway leads to the entrance, while ample parking space is visible in front of the home.

Cottage in Four Corners

4.66 out of 5 average rating, 29 reviews

5 Bed Cottage Close to Disney Parks

A comfortable living area features a dark blue sofa with matching accent pillows, paired with a coordinating ottoman. A green armchair is positioned nearby, and a small side table stands beside it. Natural light pours in through a window, illuminating the warm wood flooring.

4.74 out of 5 average rating, 142 reviews

Entire HAPPY HOME Near Disney and Universal Parks

A modern living area features a wooden accent wall, complemented by a round coffee table with flower arrangement. A flat-screen TV is mounted above and a dining area with a table and chairs is visible in the adjoining space.

4.72 out of 5 average rating, 36 reviews

Cozy Home in Davenport

The exterior of the cottage features a light blue facade, complemented by a white door and multiple windows. A screened-in sunroom extends from the front, providing a bright and airy space. Potted plants decorate the entryway, enhancing the cottage's welcoming appearance.