Holiday rentals with breakfast in Winter Haven

5 out of 5 average rating, 20 reviews

The exterior of a rustic cabin is adorned with warm string lights, creating a welcoming ambiance. A porch with steps leads up to the entrance, flanked by lush greenery. The wooden structure features a lighted wheel decoration and bright windows, giving it a charming appearance at dusk.

Cabin in Kissimmee

Authentic Disney Fort Wilderness Cabin near WDW-2

Authentic Fort Wilderness family cabin from Walt Disney World upgraded with extra classic Disney style. Welcome to our family vacation home in Kissimmee next to Celebration. 9 min. to WDW arch 18 min. to Magic Kingdom (no I-4 traffic) Sea World & Universal also nearby Beaches 1 hr. drive Shop, dining & bus service to WDW all walking distance Accommodates a large family: Full bathroom Full kitchen Queen bed 2 bunk beds Pull out double bed sofa Fold up cot All Disney quality Not Disney affiliated

4.95 out of 5 average rating, 151 reviews

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

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!

4.85 out of 5 average rating, 123 reviews

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

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

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.

4.98 out of 5 average rating, 114 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!

4.92 out of 5 average rating, 24 reviews

Dome in Davenport

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

Guest suite in Winter Haven

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.

4.88 out of 5 average rating, 25 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.

4.97 out of 5 average rating, 39 reviews

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

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!

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.

4.98 out of 5 average rating, 41 reviews

5BR Villa |2 Game Rooms |Heated Pool| 10 min Parks

✨ LUXURY 5BR DISNEY VILLA | Sleeps 16 | 10min to Parks! 🏰 🎪 THEMED ROOMS: Mickey Master, Frozen Princess, Harry Potter & Nautical 🎮 TWO GAME ROOMS: Pool table, air hockey, ping-pong, Pac-Man arcade & gaming console 🏊‍♀️ PRIVATE HEATED POOL with screened lanai & tropical landscaping ✨ Smart TVs | High-speed WiFi | Gourmet kitchen | Free parking 📍 10min to Disney | 15min to Universal | 5min to restaurants Perfect for families & groups! Book your magical vacation!⭐️⭐️⭐️⭐️⭐️

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.

4.99 out of 5 average rating, 161 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.

4.9 out of 5 average rating, 131 reviews

6 BD Insta-Worthy home - pool/cine/BBQ near Disney

Welcome to your dream getaway home for 18! Your family will embark on an incredible vacation in this extraordinary residence. Offer an incredible experience for your kids as they choose to sleep in the Star Wars, Nemo, or Mickey bedrooms, where each room offers a realm of imagination! Elevate your stay with extraordinary movie nights in our incredible theater or indulge a friendly competition in the game room! *Themed Breakfast service is optional at an additional fee.

4.92 out of 5 average rating, 216 reviews

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

$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!

5 out of 5 average rating, 5 reviews

Townhouse in Davenport

THE EPIC OASIS • Game Room • Pool • Near Disney

Welcome to The Epic Oasis, your modern family retreat just minutes from Disney! This beautifully designed home offers the perfect blend of comfort, fun, and style — featuring a full game room, themed bedrooms, and access to a resort-style pool, mini golf, water park, and more. Whether you’re here for the parks, the amenities, or a relaxing getaway, this home has everything you need for an unforgettable stay.

Popular amenities for rentals with breakfast in Winter Haven

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with breakfast

4.77 out of 5 average rating, 43 reviews

An outdoor space featuring a private tub surrounded by a patio area with two chairs. Inside, a bunk bed with blue bedding is complemented by wall decor. A dining area is seen with a round table set for six, while a cozy living room is furnished with a spacious couch and a TV.

Home in Kissimmee

Minutes to Disney/Universal w/private tub(not hot)

5 out of 5 average rating, 3 reviews

3Ks Sweet Escape – A Cozy Slice of Paradise

A private pool area is enclosed by a screened lanai, featuring a clear blue pool complemented by several lounge chairs arranged nearby. Lush greenery is visible outside the enclosure, creating a serene environment. A basketball hoop can be seen beside the pool.

4.82 out of 5 average rating, 28 reviews

Lovely villa/Ideal for long stay/txt for discounts

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

4.76 out of 5 average rating, 145 reviews

Highly Rated: Pool, Golf Views, Disney, Legoland

A private swimming pool is showcased within a screened enclosure, surrounded by a spacious patio. Sun loungers are positioned nearby, inviting relaxation. Lush greenery and palm trees create a serene backdrop, enhancing the outdoor ambiance of the property.

4.83 out of 5 average rating, 60 reviews

Modern Family Pool Home 14 Miles From Disney

The collage features four images: a vast water park with slides and swimming areas, a gaming room with a starry ceiling and minimalist decor, a recreational space with sports equipment, and a private pool surrounded by a spacious patio and lush landscaping.

Home in Four Corners

5 out of 5 average rating, 4 reviews

Star War Room & Game Room + Waterpark Access

Home in Sunridge Woods

4.73 out of 5 average rating, 41 reviews

Sunnyside at Sunridge

The exterior of the villa features a charming entrance with a distinctive arched doorway, adorned with a terracotta roof. Lush palm trees frame the entrance, and a smooth driveway leads to a spacious garage on the right.

4.71 out of 5 average rating, 107 reviews

7 Bdrs, 14 beds, 7 baths heated pool & near Disney

Apartment rentals with breakfast

A spacious bedroom features a large bed with neutral bedding and a decorative wall art piece. A wooden dresser is positioned against the wall, and a television sits atop it. Natural light enters through a large window, complemented by sheer curtains. A bench is placed at the foot of the bed.

4.67 out of 5 average rating, 63 reviews

2BR. Condo-Resort, 2min. from Disney World!!- 72

5 out of 5 average rating, 6 reviews

NO Resort Fees 10 mins to Disney! FREE Breakfast!

4.5 out of 5 average rating, 6 reviews

A crystal-clear pool is surrounded by lush palm trees and a spacious deck with lounge chairs. The pool area is bathed in sunlight, featuring a gentle slope into the water and adjacent clubhouse with shaded areas for relaxation.

Flat in Kissimmee

15 Mins or less from Universal/Disney/Convention

A colorful water park features dual waterslides alongside a large swimming pool. A spacious deck with lounge chairs is visible, and shaded area beneath a thatched roof provides seating. Lush palm trees and landscaped gardens complete the tropical ambiance, enhancing the resort experience.

4.5 out of 5 average rating, 4 reviews

2 bedroom villa resort near disney world

A panoramic view captures the resort's stunning architecture surrounding a serene lake. Colorful buildings reflect warm hues under a clear sky, while a fountain in the lake adds a tranquil charm to the picturesque landscape.

5 out of 5 average rating, 5 reviews

Bonnet Creek Resort

The entrance to WorldQuest Resort is visible, featuring a decorative sign against a backdrop of lush greenery and palm trees. A circular driveway leads into the resort, under a clear blue sky dotted with fluffy clouds.

4 out of 5 average rating, 4 reviews

Disney Condo w/Great Views- 70

A modern kitchen is featured with dark cabinetry and a spacious granite countertop. Stainless steel appliances, including an oven and microwave, are present. Two barstools with colorful upholstery are situated at the countertop, providing a cozy dining area.

Flat in Kissimmee

Family fun in spacious 1BR Vacation Village

A spacious living area features a light-colored sofa with decorative pillows, two armchairs, and a coffee table. Large windows allow natural light to fill the room, offering views of the surroundings. A console cabinet and contemporary art pieces complement the modern aesthetic.

Flat in Williamsburg

Marriott's Grande Vista

Other holiday rentals with breakfast

4.86 out of 5 average rating, 29 reviews

The exterior of a two-story home is shown, featuring a light-colored façade with large windows. A vehicle is parked in the driveway, and green shrubs and a magnolia tree are visible in the well-maintained yard. Clear blue skies provide a bright backdrop.

Villa in Kissimmee

3 Miles from Disney 5/5 Pool home-free pool heat

An aerial view captures the resort's pool area surrounded by lush palm trees and landscaped gardens. A serene lake reflects the buildings and surrounding greenery. The distinct architecture of the villas is visible in the background, providing a harmonious blend with the natural landscape.

5 out of 5 average rating, 13 reviews

Disney Area Resort Without Disney Prices!

A comfortable living area features a gray sectional sofa accompanied by decorative pillows. A wooden coffee table and a small decorative piece are positioned in front. Natural light enters through a large window, with a view of greenery visible beyond the sheer curtains.

Bungalow in Davenport

4.84 out of 5 average rating, 37 reviews

Disney Vacation Home 20 mins away from Parks !

A refreshing cocktail garnished with fruit and an umbrella rests beside a bowl of strawberries near the edge of a private screened pool. Brightly colored beach toys float in the water, creating a cheerful atmosphere.

Villa in Davenport

4.75 out of 5 average rating, 24 reviews

*Last Minute deal!40% off Villa w/Pool near Disney

A modern townhome exterior is presented with a two-car garage and a charming entryway. Lush landscaping surrounds the property, featuring a verdant tree and flowering plants. The sky showcases a blend of warm pink and purple hues as the sun sets, creating a serene backdrop.

Townhouse in Championsgate Village

4.74 out of 5 average rating, 47 reviews

Cozy Townhome Fast Wifi Pools+Jacuzzi Near Disney

A cozy bedroom is presented with a spacious bed featuring a wooden headboard. Soft linens in shades of blue and grey are arranged neatly. A small bedside table with a lamp and a stack of neatly folded towels adds to the inviting atmosphere, complemented by natural light from the window.

Bungalow in Lakeland

4.75 out of 5 average rating, 102 reviews

N. Lakeland - Updated - 2 Bedroom House! ☆☆☆☆☆

4.83 out of 5 average rating, 320 reviews

A peaceful outdoor deck area features two orange wire chairs with soft black cushions positioned around a round table. A small potted flower arrangement adds a touch of color, creating an inviting space for relaxation surrounded by bamboo accents.

Farm stay in Kissimmee

Container home -near Disney WIFI Bamboo Farm