Apartment vacation rentals in Winter Haven

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

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!

Cute Upstairs Apartment 2BR/1BA Near Downtown.

This upstairs apartment features two bedrooms plus a pullout sofa in the living area, comfortably sleeping up to 6 guests. Tucked away in a quiet setting yet just one mile from downtown Winter Haven, it offers the perfect balance of peace and convenience. Enjoy ample parking for multiple vehicles, a full-size kitchen, and a comfortable living area with plenty of space to relax without feeling crowded. Located on the second floor, the apartment provides added privacy for a comfortable stay.

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 .

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!

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.

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. One Complimentary Bottle of Cabernet per Stay. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Cozy 2B/1 Downtown Hideaway

This cozy mother in law suite is a duplex that shares a wall with the main house but not an entrance. You will be blocks away from a neighborhood playground as well as beautiful Lake Hollingsworth. Being in the heart of Lakeland, you are never far from entertainment or nature. It's almost equally distant from Orlando and Tampa at about a 45-minute drive and the beach being about an hour and 20 minutes away. All that downtown has to offer is just 2 miles away.

Serenity Studio is steps from Lake Hollingsworth

Relax and unwind at Serenity Studio. This stylish space is located steps from Lake Hollingsworth in a quiet established neighborhood. Your privacy is Paramount. The studio is fully equipped with a kitchenette, washer/dryer, smart TV with high speed internet and cable connected. This is the perfect spot for a getaway!! You will leave well rested and refreshed. Welcome to Serenity Studio! This is a Pet Friendly Studio with additional pet fees.

Hidden Ruby Apartment

Your family will be close to everything when you stay at this centrally-located place. Within walking distance to restaurants, major grocery stores, parks, and much more. Midway between major cities of Orlando and Tampa for the urban seekers. Reserved guest parking, front porch sitting area, washer and dryer, work station, and a children-safe environment. This apartment was designed to accommodate all of your needs.

The Cozy Escape

Escape to our cozy 1 bed, 1 bath apartment, perfectly nestled adjacent to the main house yet completely private. Whether you're seeking a romantic couples' retreat, a productive work trip, or some well-deserved "me time," this spot has it all! After an exciting day out, unwind in our comfortable space, relax & recharge. With assigned parking, you can come & go with ease!