Waterfront holiday rentals in Osceola County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Osceola County

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

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Top guest favourite

Apartment in Kissimmee

4.95 out of 5 average rating, 187 reviews

3161-305 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Top guest favourite

The exterior of the barn showcases a rustic wooden facade beneath a metal roof. A porch with seating options invites relaxation, while the neatly maintained yard features green grass and landscaping. A driveway leads to a side garage, enhancing the property's charm and accessibility.

Barn in St. Cloud

4.97 out of 5 average rating, 167 reviews

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

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, 103 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

Top guest favourite

The living area features a modern sectional sofa with colorful throw pillows in vibrant red and yellow. A matching ottoman sits in front, accompanied by stylish side tables with lamps. Bright blue walls create a lively backdrop, enhanced by a large abstract painting and adjacent dining space.

Villa in Lake Wales

4.98 out of 5 average rating, 200 reviews

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

Top guest favourite

Home in Lake Wales

4.98 out of 5 average rating, 105 reviews

Fishing Lakefront Paradise w/ Boat Slip & Parking!

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

Superhost

A screened-in pool area is illuminated by string lights, offering a serene view of the lake at sunrise. The inviting pool features floating noodles, and the surrounding space is bordered by greenery, enhancing the tranquil atmosphere.

Home in Kissimmee

4.88 out of 5 average rating, 208 reviews

Disney & Universal Retreat| Heated Pool | Fire Pit

Sit back and relax in this stylish home with all the amenities you need for a fun family getaway. This home has a spacious layout with 3 bedrooms and 2 baths. We have thought of everything so you don't have to-toiletries,washer/dryer, and wifi. Enjoy your morning coffee in the screened in pool area with a beautiful sunrise and lake view or sip a glass of wine while floating in the pool. Just minutes to Theme Parks and major highways, this is the dream home you have been waiting for!

Top guest favourite

A modern apartment features a spacious bedroom with themed decor, showcasing vibrant wall art and a cozy sleeping area. An open kitchen adorned with sleek cabinetry and a dining space with four chairs is highlighted. A decorative living space includes a friendly mural, adding a playful touch.

Apartment in Kissimmee

4.94 out of 5 average rating, 171 reviews

302_10 Pixie Dust Paradise - 10 min from Disney

A Magical Stay for the Whole Family! Welcome to your family's happy place near Disney! Our 3-bedroom apartment is cozy, kid-friendly, and fully stocked with everything you need to feel right at home. Whether you're starting your day with excitement or coming back from the parks with tired little feet, this is the perfect place to relax and recharge. And guess what? The waterpark is FREE and super fun—a splash-tastic way to end your day with big laughs and happy memories!

Top guest favourite

An outdoor view shows a private pool, where a person is enjoying the water with a serene water view beyond. Inside, an illusion room presents colorful decorations and a lively atmosphere. A cozy bedroom showcases a spacious bed adorned with soft linens. A game room is visible, featuring engaging entertainment options.

Home in Kissimmee

4.99 out of 5 average rating, 141 reviews

[20% OFF] Illusion Home •Waterfront Private Pool

❤ Illusion room with character outfits ❤ Private pool with water view ❤ 15 min to Disney ❤ 25 min to Universal, SeaWorld, Convention Center, 2 min to Walmart ❤ Game room with board games & kids toys ❤ 100" movie theater screen ❤ Free Netflix ❤ Fully equipped kitchen ❤ Sleeps 12 ppl ❤ 2 king beds, 2 cribs, 1 Queen memory foam sofa bed, 6 twins ❤ Newly renovated home ❤ Fully stocked home ❤ Alice in Wonderland®-themed home ‼️ No parties, No smoking, 4 dogs max $75/pet

Top guest favourite

An expansive outdoor pool deck is featured, surrounded by lounge seating and shaded areas. A giant outdoor chess set stands nearby, along with a view of the scenic forest and pond. A brightly decorated game area showcases themed decor and entertainment options.

Home in Four Corners

4.99 out of 5 average rating, 151 reviews

*Luxurious Paradise Mansion: Pool, Spa & Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT in the stunning 3.5 square mile Reunion Resort. You will have your own private pool, spa, movie theater - game room, 3 master suites, 3 incredible themed bedrooms (MARVEL, FROZEN II, NASA) for kids or adults, the latest Xbox Series X game station, a 2500 ft2 pool deck overlooking a beautiful forest and pond, fire pit, & billiards table, minutes to Disney.

Top guest favourite

The image displays a resort landscape featuring various pastel-colored buildings surrounding a large pool area. A view of the tranquil lake is visible, with numerous palm trees and lounge chairs positioned near the water. The highlighted apartment is located on the second floor of one building.

Apartment in Kissimmee

4.97 out of 5 average rating, 398 reviews

Gorgeous❤️ Pool & Lake View Condo near Disney Parks

Welcome to Runaway Beach Club — your peaceful escape just minutes from the magic! With airy high ceilings and Key West-style decor, you’ll feel at home the moment you walk in. Whether you’re visiting theme parks or just want to relax, this cozy retreat is tucked away from the chaos but close to everything. Perfect for couples, small families, or business travelers. Book your stay and unwind in your own private slice of paradise!

Top guest favourite

The collage showcases various areas of the lakeside home. Highlights include a private patio dining set, a resort-style pool, a comfortable living space with a dining table, and vibrant bedrooms featuring bunk beds and colorful decor. The picturesque lake view complements the outdoor spaces.

Townhouse in Kissimmee

4.99 out of 5 average rating, 131 reviews

Lake View - 5 Miles to Disney!

This family friendly lakeside home is just five miles from your favorite theme parks and surrounded by a multitude of dining options, retail shopping, grocery stores and entertainment right outside the resort. This smart home offers high-speed internet/wifi and endless entertainment is just a voice command away. This home is located within the popular gated Encantada resort (staffed by security personnel 24 hours a day).

Guest favourite

Flat in Kissimmee

4.83 out of 5 average rating, 160 reviews

Spacious Apartment near Disney

Welcome to our cozy and inviting apartment in the heart of The Loop, Kissimmee! Ideally located for both convenience and comfort, this charming space is perfect for couples, solo travelers, business professionals, and those looking for extended stays. Whether you're here for a magical Disney vacation, a work trip, or a romantic escape, our apartment offers the perfect home away from home for all your adventures.