Apartment holiday rentals in Winter Haven

5.0 out of 5 average rating, 44 reviews

A circular fire pit area is surrounded by multiple light gray Adirondack chairs on a stone patio. The fire pit is filled with glowing flames, creating a cozy atmosphere against a backdrop of a calm lake at dusk, with soft colors in the sky.

Flat in Winter Haven

Luxury by Legoland 104

Experience comfort and convenience in this stylish 2-bedroom, 2-bathroom apartment, located less than one mile from the LEGOLAND entrance. Situated in a brand-new 2024 luxury complex, this ground-floor unit offers a seamless blend of relaxation & entertainment, perfect for families and theme park enthusiasts. Amenities & Features: • Resort-style heated pool • State-of-the-art fitness center • Fire pits, BBQ grills, and picnic spaces • LEGOLAND-themed kids’ bedroom for a fun, immersive stay

4.98 out of 5 average rating, 181 reviews

A balcony view overlooks a serene lake, framed by lush palm trees and vibrant green foliage. Bright blue skies and scattered clouds add to the tranquil setting, while glimpses of the driveway and nearby structures can be seen in the distance.

Flat in Winter Haven

Florida Penthouse in luxurious mansion!

Stay in your own themed Florida apartment . Tropical, palm trees, beaches ,marine life, flamingos throughout this stunning apartment in a multimillion dollar home. After parking on gated driveway walk up to your own private entrance way to paradise. Keyless entrance. One flight up and your viewing gorgeous lake views second to none. Executive kitchen with everything you need to cook a 5 course meal. Outdoor balcony that will leave you amazed. Opulence, security, with Florida Style awaits you!

A comfortable living area features a light gray sofa with decorative pillows, complemented by a dark coffee table placed on a colorful area rug. Natural light fills the space through large windows with sheer curtains, and a potted plant adds a touch of greenery.

4.89 out of 5 average rating, 434 reviews

Cozy Downtown Hideaway with Butterfly Garden.

Escape to this charming and comfortable mother-in-law suite, a private duplex that shares only a wall with the main house, no shared entrance. Just blocks away, is Dobbins Park and the scenic beauty of Lake Hollingsworth for peaceful walks and stunning sunsets. Downtown: 2 miles Colleges: about 10-15 mins each Orlando & Tampa: ~45 mins each Gulf beaches: ~1 hour 10 mins Perfect for weekend getaways, family visits, business, or extended stays. Your peaceful home base in Lakeland awaits!

The bedroom features a large tufted bed with soft linens, complemented by a decorative bench at the foot. Industrial-style accents are visible in the exposed brick wall and ceiling beams, while natural light fills the space through floor-to-ceiling windows, framed by navy curtains.

4.95 out of 5 average rating, 103 reviews

Downtown Lkld-Urban Luxury Loft

Discover urban comfort in our Downtown Lakeland Studio Loft! This trendy third floor apartment accommodates 4 guests, boasting open industrial ceilings and historic brick walls that add a chic touch to the space. The floor to ceiling windows bring in gorgeous natural sunlight. Step outside and immerse yourself in the heart of the city, with cafes, shops, and attractions just a stroll away. Whether you're here for business or leisure, our loft offers the perfect blend of style and convenience!

4.99 out of 5 average rating, 137 reviews

Matty’s Citrus Connection

You are going to love this Citrus themed hideaway with its Old Florida feel that takes you back to simpler times. Rest and relax in this backyard paradise while enjoying all that Lakeland has to offer. Whether you choose a relaxing day enjoying the many local activities , take a day trip to a beautiful Florida-beach , or decide to visit one of Florida’s theme parks , this is the place to stay . We are centrally located and have quick access to Polk Pkwy , so your adventures are unlimited .

A bright workspace is showcased with large windows offering views of the lake. Two yellow armchairs sit beside a glass-top table. A desk with a lamp is positioned against the wall, with a potted plant adding a touch of greenery.

5.0 out of 5 average rating, 154 reviews

Romantic Lakefront – Feed Swans – Walkable Dining

Discover SWAN LAKE VACATIONS. Swan elegance meets city charm steps away. Highlights: • Lake Views • Downtown Stroll • King-sized bed • Modern Comfort • Full Kitchen • Semiprivate Patio • Between Tampa & Orlando Why Swan Lake Vacations? • Central Hub • Safety Assurance • Easy drive to beaches and Walt Disney World • Experienced Hosts Escape to Swan Lake Vacations—a place where swans grace the surroundings next to quaint downtown life. Book for a perfect blend of nature and urban comfort!

4.9 out of 5 average rating, 109 reviews

Aerial view of the pool area shows vibrant water slides winding through landscaped surroundings. Multiple swimming pools can be seen, complemented by palm trees and open spaces. Sun loungers are arranged around the pools, offering ample relaxation spots for guests.

Flat in Kissimmee

Apartment in Four Corners

Escape to this stylish 2-bedroom, 2-bathroom condo, perfect for families or friends seeking a memorable getaway. Enjoy spacious living area, complete with a comfortable sofa bed, and a fully-equipped kitchen. Relax in luxury with a king-size bed and en-suite bathroom. Access at NO ADDITIONAL cost to world-class pools, a lazy river, and a fitness center . Enjoy complimentary Wi-Fi and parking Located in the heart of Champions Gate, Aprox. 15 mins to Disney Parks & 30mins to Universal

5.0 out of 5 average rating, 48 reviews

A bright sleeping area features a wooden bed frame with a neutral-toned bedspread, accented by a decorative orange pillow. A green chair sits beside a nightstand with lamps. Wall art and a textured hanging piece add character, while natural light filters through the curtains.

Flat in Winter Haven

Cozy Boho Studio

Welcome to this cozy and stylish retreat! This is a separate private apartment attached to our home. It is cozy and very clean. This thoughtfully designed living space combines modern elegance with comfort, perfect for unwinding after a day of exploring. The space is ideal for relaxing or catching up on your favorite shows. The space has a warm couch/futon and everything you need to feel at home. Ideal for solo travelers or couples looking for a comfortable and stylish getaway.

A cozy living area features hardwood floors and large windows allowing natural light. The space includes a brown sofa and a wooden coffee table placed on a patterned rug. A small dining area with two chairs and a kitchen nook with appliances is visible in the background.

4.94 out of 5 average rating, 103 reviews

Eclectic On The Alley

1925 Historic Downstairs Garage Apartment in the highly desired Dixieland District, that has antiquing, restaurants, bakeries, coffee shops, and more...all within walking distance! Within a block from either side of the house is Reececliffe Diner and Patio 850, that's a restaurant and wine bar. It’s a lovely five minute walk to Lake Morton, home of the swans, from which our nickname “Swan City” hails. You can easily walk to downtown, which is a total of one mile from the house.

4.97 out of 5 average rating, 103 reviews

Flat in Davenport

Spacious 4 Bedroom Condo Resort Near Disney

Affordable condo located in a relaxing and safe Mediterranean style resort community near Orlando parks. Plenty of space for large families and or many friends! The community’s amenities include two heated pools, a jacuzzi, a splash pad, outdoor kitchen areas, and a fitness center. There are many restaurants and shops nearly within walking distance of the condo. You will save a lot of money on your family vacation by staying here compared to theme park hotels!

4.96 out of 5 average rating, 268 reviews

A wooden deck overlooks the calm waters of Lake Ariana, framed by greenery. A small table with two chairs is positioned to enjoy the view, while a potted plant adds a touch of nature to the space. Spanish moss drapes gracefully from nearby branches.

Flat in Auburndale

Ariana Place - Tree House Like Lakefront Views

An Upstairs Sumptuous Tree house (like) Apt on Lake Ariana Waterfront. Upper Outside Deck with chairs & table. Quiet and tranquil with Hi-Speed Wifi for Business Travelers, Smart Antenna TV and Incredible Views for Romantic Get-Aways. Located near Disney, Legoland & Busch Gardens in Central Florida. Luxurious Bedding, Full Kitchen with Coffee & Wine Bar. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly.

The spacious bedroom features a queen-sized bed dressed in neutral linens. Light filters through sheer curtains, illuminating a dresser and a television. A bedside lamp adds functionality, while decorative elements enhance the calming decor of the room.