Holiday rentals with breakfast in Winter Haven

Find and book unique Holiday Accommodation with Breakfast on Airbnb

Quick stats about holiday rentals with breakfast included in Winter Haven

Total holiday rentals
Explore 10 holiday rentals in Winter Haven
Nightly prices starting at
Winter Haven holiday rentals start at $85 AUD per night before taxes and fees
Verified guest reviews
Over 20 verified reviews to help you choose
Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 of Winter Haven holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Haven rentals
4.9 Average rating
Winter Haven stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated Holiday Accommodation with Breakfast in Winter Haven

Guests agree: These breakfast rentals are highly rated for location, cleanliness and more.

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Superhost

Home in Clermont

5.0 out of 5 average rating, 5 reviews

Game room + pool home near Orlando's top parks

Step into this fun-filled Orlando area pool home - perfect for families & groups chasing theme parks, resort-style outdoor fun & loads of in-home entertainment! 🛏 Sleeps 10 | 4 bedrooms | 5 beds | 2 baths 🏊 Private pool & spa (heating for a fee) + fireplace & BBQ grill 🎮 Game room w/ arcade, pool table, ping pong & Smart TV 🎢 19 mins to Disney, 26 mins to Universal, 10 mins to Island H2O 👨‍👩‍👧 Family-ready w/ pack 'n play, high chair & themed rooms 🐾 Pets welcome (approval required)

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Top Guest favourite

Home in Plant City

5.0 out of 5 average rating, 52 reviews

Farmhouse Oasis w Treehouse, Spa, Pool & Arcade i4

Adventure Farmhouse w/ Pool, Game Room & Treehouse – Near Tampa & Lakeland Welcome to your ultimate getaway—a stunning navy blue farmhouse set on over an acre of private land, just minutes from both Tampa and Lakeland. This isn’t just a home—it’s a full-scale adventure retreat designed for families, friends, and unforgettable memories. Relax under oak trees, dive into the huge pool, grill on the deck, or enjoy movies in the treehouse theater—this unique retreat has something for everyone!

ValueFamilyNearby

Top Guest favourite

Home in Davenport

4.98 out of 5 average rating, 125 reviews

Disney Magic Awaits- Featured in WDW Magazine!

Welcome to Your Custom-Crafted Dream Vacation! Our uniquely designed home offers an extraordinary experience for your family’s ultimate getaway. Thoughtfully curated, it creates a serene retreat while your kids enjoy themed rooms, play areas, and activities. We’ve brought Disney magic to your doorstep, ensuring cherished family memories. With personalized touches and exclusive amenities, our home delivers a vacation like no other—proudly featured in WDW Magazine! See the magic in photos!

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Guest favourite

A wooden house is situated beside a deep water canal, with lush greenery surrounding the property. A dock is visible at the water's edge, alongside a small area for outdoor seating. The structure features an upper deck and is complemented by a neatly landscaped yard.

Guest suite in Haines City

4.92 out of 5 average rating, 112 reviews

1 BR 1BA Lake Apt. Boat slip, Deck, Pets, Laundry

Come wake up to birds singing, looking out your windows to a nice deep water canal view. The canal leads to Lake Hatchineha (great fishing). TVs in every room. Fully loaded kitchen; private entrance. There is a porch, laundry and deck area shared with one other apt. Free laundry . We are 45 min from MCO(airport) 45 min from Disney and 15 minutes to Legoland. Bok Towers is a unique park that is 18 miles away. Star gazing and bicycling or fishing. Port 27 is 20 min with fun food and drinks

ValueFamilyTV

Superhost

Dome in Davenport

4.88 out of 5 average rating, 41 reviews

Modern Domes | Pool | Hot Tub Private Retreat!

Reserve your stay with us now and take advantage of the following amenities: Newly Built- Our facilities are completely new Climate Control- Enjoy cold AC/heat with fans and full insulation for comfort Complete Privacy Pool with pool toys and floats Hot Tub High-Speed WiFi Coffee Bar Hammock for Two Entertainment- TV with Netflix, Hulu, etc. Private Outdoor Shower- Enjoy a hot shower in a secluded setting. Private Fire Pit Variety of Games Secure Location- Gated area with keypad entry

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Superhost

A serene outdoor space features a small pond with a fountain, enclosed by a white lattice. Two white chairs and a table are positioned beside a potted flower arrangement, creating an inviting spot for relaxation amidst the greenery.

Guest suite in Winter Haven

4.9 out of 5 average rating, 31 reviews

Cozy Family Vacation Villa

An Airbnb for the family. Loaded with lots of extras and goodies to make your stay comfortable and convenient. Every cable channel possible including all the premiums. The house comes to life at night with mood lighting in the yard and villa. Private self check in and parking w free laundry facilities on the property. Designed with families in mind offering something for everyone. Family parties and events welcome. Lots of parking. Ask about complimentary chef services for my guests.

LocationFamilyKitchen

Superhost

Townhouse in Kissimmee

4.75 out of 5 average rating, 115 reviews

Incredible 4 BD home w/ Pool&BBQ - near Disney!

Welcome to our enchanting home for 8! Discover a perfect blend of comfort and charm in this expansive retreat. Our prime location places you just minutes away from the magic of Disney, the thrills of Universal Studios, a wide array of exclusive dining options, outlet shopping, and much more! Escape to your own private pool and grill area for quality family time. This beautiful property offers everything you need to unwind. *Themed Breakfast service is optional at an additional fee.

FamilyLocationLong stay

Top Guest favourite

A cozy living space features rustic sliding barn doors that open to reveal a stylish sleeping area. A queen-sized bed is neatly arranged with soft bedding, while ample natural light enters through large windows, illuminating the wooden ceiling and floor.

Cabin in Davenport

4.98 out of 5 average rating, 59 reviews

Relax Away Retreat | Cozy Cabin

Book with us now and receive access to all of these amenities: •Lightning Fast Internet •Mini Golf & Plenty of Games •Private Fire Pit •Private Swinging Bench •Covered Patio •Safe Gated Location •Keypad Entry Door •Comfortable Queen Sized Bed •TV (Adjustable) •Modernized Brand New Full Bathroom •Outdoor Dining Area •Kitchen, Fridge/Freezer, & Breakfast Nook •Complimentary Coffee & Breakfast •Cooking Equipment •Nearby All Major Attractions •And Much More! Book with us now!

ValueLocationQuiet

Top Guest favourite

A vibrant game room features arcade machines themed around racing and superheroes. Adjacent, an outdoor space showcases a heated pool and hot tub, complemented by a fully equipped kitchen. The playful bedrooms are designed for immersive adventures inspired by Toy Story and Marvel.

Home in Davenport

4.99 out of 5 average rating, 176 reviews

Spectacular! Disney/Universal Themed Home

Welcome to a truly unforgettable, one-of-a-kind Luxury themed home!! Inside, discover a custom-built pool table made from real car parts, two professional Mario Kart arcade machines, and 14 strategically placed TVs—guaranteeing nonstop entertainment in every room. Step outside into your private oasis, complete with a fully equipped summer kitchen, immersive surround sound, and outdoor TVs perfectly positioned so you can enjoy your favorite movies from the hot tub or pool.

LocationValueCondition

Top Guest favourite

A charming villa exterior is displayed, featuring a spacious driveway and a manicured lawn. Palm trees frame the entrance, adding a tropical touch. The home is painted in warm tones, with large windows that enhance natural light. A serene sunset sky fills the background with subtle hues.

Home in Davenport

4.98 out of 5 average rating, 46 reviews

5BR Disney Pool Villa | Game Room | Sleeps 16

✨ Magical 5BR Disney Villa with themed rooms: 🏰 Mickey Master Suite, ❄️ Frozen Princess room, ⚡ Harry Potter Wizard room, ⚓ Nautical room & luxurious Adult Master! 🎮 Two awesome games rooms feature pool table, table tennis, air hockey, big-screen gaming & Pac-Man arcade! 🏊‍♀️ Stunning private swimming pool & relaxing outdoor area for ultimate fun! 🎢 Just minutes from Disney World & Universal Studios - your perfect magical family holiday awaits! Book now! 🌟

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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.

Cottage in Davenport

4.93 out of 5 average rating, 227 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!

FamilyLocationPets

Superhost

A bright living space features a comfortable sofa and a vintage trunk as a coffee table. This area includes a dining table set for four and a compact kitchen with bar seating. Natural light fills the room through large windows, highlighting colorful wall art.

Guesthouse in Davenport

4.88 out of 5 average rating, 218 reviews

Winsome Farm Guest House

*Rest, *Relax, *Refresh, *Renew Here! Business travel? Vacationing? Escape the hectic pace but be nearby to all Central Florida amusements, restaurants, shopping, theater. Mid-way between east and west coast beaches. Large screened back porch overlooks nature conservancy. Farm to table fresh vegetables and fruits in seasonal garden right out your door and daily fresh eggs, should you choose to cook in fully outfitted kitchen or electric grill outside.

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