Holiday rentals with breakfast in Winter Haven

Find and book unique rentals with breakfast on Airbnb

Top-rated rentals with breakfast in Winter Haven

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

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Top guest favourite
The exterior of the single-family home features a manicured lawn with lush greenery and vibrant plants. A spacious driveway leads to a garage, while decorative landscaping enhances the inviting atmosphere of the front yard.
Home in Lakeshore
4.97 out of 5 average rating, 146 reviews

Clean Lakeland Home w/ Water Views & RV Parking!!!

This super clean, cute as a button Single Family Home provides ample parking with a huge fenced in backyard perfect for your short-term stay! You will find thoughtful touches throughout like USB Wall Outlets and complimentary bicycles! Conveniently located at the center of Lakeland, just minutes of a walk to Lakeland Regional Medical Center (Hospital) along with the newly constructed Carol Jenkins Women's Center. This home has it all and anxiously awaits your arrival to begin making memories!

Guest favourite
A spacious community pool is surrounded by lounge chairs and seating areas, offering a relaxing atmosphere. Lush greenery and trees can be seen in the background, while a clubhouse with large windows is visible to the right of the pool.
Apartment in Winter Haven
5 out of 5 average rating, 9 reviews

Condo on Lake Lulu

This upstairs condo is the perfect getaway, offering a spacious and comfortable stay with lakefront views of Lake Lulu on the Chain of Lakes. Featuring two bedrooms, each with its own attached ensuite master bathroom. The fully stocked kitchen includes everything needed for home cooking. Step outside to enjoy the screened-in balcony. Located in a community with a heated pool, this rental offers relaxation and resort-style amenities, making it ideal for extended stays. Only 3.7 miles to Legoland

Superhost
Two lounge chairs are positioned beside a heated pool, overlooking a serene lake. A pink flamingo pool float rests nearby. The outdoor area includes a large umbrella for shade, creating a peaceful space for relaxation.
Home in Kissimmee
4.85 out of 5 average rating, 115 reviews

Dreamy Waterside Villa | Heated Pool & Near Disney

Experience a quiet waterfront villa, this stunning property offers breathtaking views, luxurious amenities, and prime location for your getaway. Relax by the pool enjoying the unwind lake view, With spacious interiors, modern furnishings, and impeccable attention to detail. Whether you're seeking relaxation or adventure, is your perfect vacation home. Book your stay at our stunning home and create unforgettable memories with your loved ones. NO PARTIES/NO SMOKE $50 pet fee $35 pool heater fee

Guest favourite
Flat in Orlando
4.92 out of 5 average rating, 116 reviews

5 Minutes to Disney Free Shuttle King & queen bed

* FREE SHUTTLES * PREMIUM OUTLET MALL * EPIC * DISNEY * UNIVERSAL & SEA WORLD * FREE PARKING * NO RESORT FEE* Margarita Machine * Coffee Bar * Kitchen * Private Pool View Suite * 1 Bath * 1 KING BED 1 QUEEN * ADJUSTABLE BASE BEDS! Disney Springs 2 miles, Universal & Epic 6 miles * Heated Pool * Hot Tub * Gas BBQ Grills & Pizza Oven * OnSite Stroller Rental * Onsite Laundry * Ice Machines * Basketball * Game Room * Walk to Restaurant's & Shopping * Plush towels & Linens * MCO airport 20 Minutes

Top guest favourite
A collage of vibrant images showcases various amenities, including a secluded pool area, themed rooms, and a whimsical tunnel. A playful Trolls-themed section captures children's creativity, while a modern game room highlights entertainment options. An inviting outdoor space complements the overall family-friendly atmosphere.
Home in Championsgate Village
4.98 out of 5 average rating, 110 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!

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
4.88 out of 5 average rating, 24 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.

Superhost
A light-filled living area features a wall-mounted television displaying a vibrant scene. Two blue chairs are positioned around a wooden coffee table, which is topped with a small plant. Greenery adds a touch of nature, and a patterned rug enhances the space's comfort.
Home in Haines City
4.78 out of 5 average rating, 142 reviews

Highly Rated: Pool, Golf Views, Disney, Legoland

Welcome to your ultimate 3BR/2BA getaway—where every day feels like a highlight reel! 🏡💫 💦 Dive, splash, repeat in your private pool ⛳ Sip, savor & soak in those dreamy golf views 🎢 Disney, Universal & Legoland? Just minutes away! Perfect for family fun or golf-lover escapes, this stylish retreat brings modern vibes, a chef-ready kitchen 🍳, and oh-so-comfy chill zones 🛋️. ✨ Like a resort, but all yours! Book now & let the good times roll! 🌴🎉 🌟 Let the memories begin! 😎

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
4.96 out of 5 average rating, 25 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!

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, 154 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.

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
4.92 out of 5 average rating, 213 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!

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.
Guest house in Davenport
4.89 out of 5 average rating, 205 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.​

Guest favourite
An inviting sleeping area features a spacious bed adorned with decorative pillows and a quilt. A window allows natural light to fill the room, complemented by soft curtains. A ceiling fan circulates air, while a chair and mirror provide additional functional touches.
Guest house in Winter Haven
4.86 out of 5 average rating, 207 reviews

Brutus Way Cottage, a cosy hide away

Enjoy a quick get away at Brutus Way Cottage. It is located to the rear of Lili Haven Bed N Breakfast. On your picturesque drive around Lake Howard, with its walking trail, you will take a right onto a quaint curvy lane known as S. Lake Cannon Drive NW . Be my guest at the cottage surrounded by flowers ; the cottage is nestled in the trees to the back past the Iron gates. Use of the Laundry room available upon request.

Popular amenities for rentals with breakfast in Winter Haven

Quick stats about holiday rentals with breakfast included in Winter Haven

  • Total holiday rentals

    Explore 20 holiday rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven holiday rentals start at £44 per night before taxes and fees

  • Verified guest reviews

    Over 230 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Winter Haven holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Haven rentals

  • 5 Average rating

    Winter Haven stays are highly rated by guests – averaging 5 out of 5!

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