Apartment holiday rentals in Winter Haven

4.95 out of 5 average rating, 19 reviews

Serene, Lakefront home with large screened porch!

Cozy meets calm at this quaint lakefront home. Come relax under the large covered back porch with ample seating and watch the sun rise and set. We are located on the Chain of Lakes in Winter Haven, where the waterfront view welcomes you to Florida living. We invite you to bring your kayaks, boats and jet skis. With a washer and dryer on property, and sleeping accommodations for up to 7, you have enough space for the entire family. Please note the Jacuzzi is out of service until October 2026.

An outdoor fire pit is surrounded by several wooden Adirondack chairs on a patio. The flames flicker brightly, reflecting in the water beyond, which is visible under a soft sunset glow. A serene landscape is framed by a black railing.

4.97 out of 5 average rating, 38 reviews

Luxury by Legoland 106

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

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.

4.98 out of 5 average rating, 175 reviews

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, 422 reviews

Cozy Hideaway W/ Big Yard and Wildflower 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!

Superhost

A spacious swimming pool is surrounded by palm trees and landscaped gardens. Lounge chairs line the poolside, offering a place to relax. The resort's clubhouse is visible in the background, showcasing a welcoming design with large windows.

Apartment in Davenport

4.87 out of 5 average rating, 299 reviews

Recently Award Winning Renovated 2+2 Near Disney

Tuscana Resort Orlando, is beautifully landscaped with lush planting and a private woodland. Tuscana Resorts has received the Certificate of Excellence from TripAdvisor for 5 years running! Located 10 minutes from Disney World and overlooking the world famous champions gate golf course, this resort is equipped all the amenities to ensure an enjoyable stay; a large swimming pool complex with separate kiddie pool, hot tub, 30 seat cinema, fitness center, bbq areas, picnic tables, free wifi.

4.99 out of 5 average rating, 121 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 out of 5 average rating, 140 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!

4.94 out of 5 average rating, 16 reviews

Cozy 1BR Duplex Near Legoland® | Sleeps 4

Enjoy a comfortable stay in this cozy 1-bedroom, 1-bath duplex unit near LEGOLAND® Florida. Perfect for couples, or friends, this private unit sleeps up to 4 and offers a smart layout with a fully equipped kitchen, fast Wi-Fi, and easy self check-in. Located in a quiet central located Winter Haven neighborhood with free on-site parking, it’s a great home base for theme park visits or exploring local dining and shops. Clean, compact, and thoughtfully stocked for a stress-free stay.

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, 101 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.

A modern kitchen area is depicted, featuring a black refrigerator and a microwave mounted above it. Dark wood cabinetry provides ample storage, and a silver kitchen sink is positioned next to a coffee maker. A decorative plant adds a touch of greenery to the countertop.

4.83 out of 5 average rating, 139 reviews

❤️ Brand New Modern Studio Perfect for Long Stays

This modern and private modern studio has space for three people, located in one of the best areas of Lakeland, less than 1 mile from Lake Hollingsworth, close to downtown Lakeland and major universities. Close to Disney World and 1 hour from Clear Water Beach. It is a central but quiet neighborhood, close to Publix supermarket, restaurants, gas station and laundry. Without a doubt, a cozy space !!! Don’t hesitate to ask if you have any questions.

4.96 out of 5 average rating, 262 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.

Apartment 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.