Cottage vacation rentals in Winter Haven

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, 178 reviews

Modern Vacation Cottage near Walt Disney World

Our cozy, modern vacation cottage is nestled in a quiet, private community just 4 miles from Walt Disney World and convenient to all the fun that Orlando has to offer. The cottage features 1 bedroom with a high-quality queen bed, a living room, a full bathroom, and a fully-stocked kitchen with a new dishwasher, refrigerator, microwave, and oven. Centrally located to all of the Orlando attractions, our cottage is a very comfortable and special place to enjoy all of the magic and sunshine of FL!

4.97 out of 5 average rating, 148 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!

A cozy living area showcases a rattan sofa adorned with patterned cushions. The walls are decorated with unique artwork, native artifacts, and framed pictures. Lush tropical accents and colorful lighting fixtures create a vibrant yet tranquil atmosphere. Natural light filters through decorative window panes.

4.99 out of 5 average rating, 176 reviews

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

4.85 out of 5 average rating, 227 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!

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, 164 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, 217 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, 127 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 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, 282 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!

4.91 out of 5 average rating, 176 reviews

Cottage in Lakeland

Historic 2BR Cottage w/ Fenced in Yard Near FSC

📍The Cottage — The neighborhood is laden with beautiful paved brick roads and is very peaceful. You'll be 4 minutes walking distance to Florida Southern College. Downtown Lakeland & Lake Hollingsworth are both less than 2 miles away. What you'll love: → The proximity to all of Lakeland → Onsite washer & dryer → 50” or larger Smart TVs for streaming → Dog friendly accommodation → Fully fenced in backyard → Patio with Pellet Grill and hammocks (grill pellets not provided)

A sleeping area is equipped with a spacious bed adorned with navy and white accents. Neutral wall colors complement decorative framed wall art. A bedside table and lamp are positioned beside the bed, with a welcoming pillow displayed prominently. The entry to a well-lit kitchen is visible in the background.

4.92 out of 5 average rating, 420 reviews

Bungalow cottage close to Disney Universal, for 4!

A full cottage for 4! The perfect place. Located just 20 minutes from Disney and Universal. Shopping and Restaurants are less than 5 minutes from the cottages. All new furnishings, fresh linens, fresh paint! Privately owned. This cottage is our favorite!!! We also just updated the A/C. Check our unit. We also have three other cottages on property, the Bitty Belle, Bitty Bliss, and the Bitty Blossom. All cottages are within 70 yards of each other.

Superhost

A spacious bedroom is displayed, featuring a cozy bed adorned with neutral-toned bedding and green accents. Sliding wooden barn doors provide a modern touch, while natural light filters through partially curtained windows, highlighting the room's inviting atmosphere.

4.92 out of 5 average rating, 203 reviews

$69! Cozy Cottage + Outdoor Fun -Close to Disney!

Book with us now and receive access to all of these amenities✨: •Lightning Fast Internet ⚡️ •Outdoor Movie Theater 🎥 •Ping Ping Table/Pool Table 🏓🎱 •Complimentary Coffee & Breakfast ☕️ •Safe Gated Location •Large Enclosed Covered Patio •Comfortable Queen Sized Bed •Cable TV (Adjustable) •Modernized Brand New Full Bathroom •Nearby All Major Attractions •Outdoor Dining Area •Kitchen, Fridge/Freezer, & Breakfast Nook •And Much More! Book with us now!

Popular amenities for Winter Haven cottage rentals

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.

5 out of 5 average rating, 15 reviews

Mickey's Hideaway Cottage - 5 miles from Disney!

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.

4.91 out of 5 average rating, 220 reviews

Cozy Private Cottage 5 miles from Disney!

Superhost

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, 152 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

4.8 out of 5 average rating, 15 reviews

Cozy Tiny Home Getaway minutes from Disney

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, 201 reviews

Magical Family Escape | Disney | Epic Universe

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.

4.78 out of 5 average rating, 124 reviews

Cozy Cottage 5mins From Disney Parks!

4.86 out of 5 average rating, 57 reviews

5 miles from Disney & Universal!

Pet-friendly cottage rentals

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

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.

4.67 out of 5 average rating, 162 reviews

Flexible Early Check ins / Late Check outs*

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.

4.83 out of 5 average rating, 292 reviews

Private Cottage. Only 5 miles from 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, 87 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.

4.84 out of 5 average rating, 121 reviews

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

A modern kitchen is presented, featuring sleek white cabinetry and granite countertops. An island with bar seating is adorned with greenery. Natural light filters through window blinds, illuminating stainless steel appliances and open shelving. A coffee maker is positioned on the counter.

4.61 out of 5 average rating, 62 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, 142 reviews

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

A charming blue cottage presents a welcoming facade, featuring colorful floral decorations. A spacious driveway allows for parking, while a screened porch extends along one side. Lush greenery adorns the landscape, enhancing the property's inviting curb appeal.

4.9 out of 5 average rating, 10 reviews

This must be the place

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.

4.68 out of 5 average rating, 41 reviews

The Cozy Porch

Superhost

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.

4.82 out of 5 average rating, 158 reviews

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

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

4.64 out of 5 average rating, 28 reviews

5 Bed Cottage Close to Disney Parks

4.96 out of 5 average rating, 107 reviews

Cottage of Charms

The cottage's exterior features a charming facade with a blue awning over the front door and flower pots positioned at the entrance. A spacious driveway offers parking space. In the background, the covered patio is illuminated, showcasing an outdoor dining area for gatherings.

Cottage in Lake Hollingsworth

5 out of 5 average rating, 38 reviews

Comfortable Lakeland Cottage Retreat

The exterior of a charming single-story home features a welcoming front porch with wooden steps. Large windows allow natural light to fill the interior. Surrounding greenery includes shrubs and small plants, contributing to a pleasant outdoor space under a partly cloudy sky.

4.85 out of 5 average rating, 146 reviews

2 - Ships Ahoy Bungalow 2 bed/2 bath - Unit 17

A welcoming porch area features two white rocking chairs adorned with red cushions, positioned around a small round table. A colorful rug lies beneath, while natural light illuminates the space, providing a calm setting for relaxation.

4.95 out of 5 average rating, 496 reviews

Entire cottage for 5, close to Disney, Universal!

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.