Vacation rentals 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!

Adorable Agave Suite w/ private pool and entrance

Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your “shome” away from home. Upon entry of the the property you will find a private entrance, covered parking, private screened in pool and mature trees. Your guesthouse comes equipped with 1 cozy queen size bed, pull-out sofa bed, walk-in shower, kitchenette, smart tv, wifi and more. Looking to explore? We are centrally located to your nearest parks & Florida attractions. Close to fishing docks & bike trails.

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!

Gorgeous Gem in the Heart of Lakeland

LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

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

Roe Family Lake House (Lake Mcleod)

We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the kayaks we provide on site!

Legoland Lakehouse Canoe & Kayak Retreat

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

Private Poolside Villa

Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. The apartment is behind my personal home with no connecting doors. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Cute & Cozy in Winter Haven, Florida

The guesthouse Cute & Cozy is private yet adjacent to the main house (owner lives) and has its own entrance. Located in central Florida, between Orlando and Tampa; 3 miles from Legoland, 5-10 minute walk from shopping and restaurants on Cypress Gardens Blvd. The Cute & Cozy is also in a great location from Florida's amazing beaches, just under 2 hours east or west. Maybe an hour drive to Disney, SeaWorld and Universal (depends traffic)

4 a Tiny House w/ Bunk Bed in Quiet Marina Unit 14

Our cozy tiny house is perfect for when less is more :-). An intimate space for a long reflective weekend or a more affordable option for a few days with the kids at nearby Legoland. Offering a queen-size Murphy bed and two additional single-size bunk beds, the Cypress Inlet Tiny House can comfortably accommodate up to four people. Equipped with a mini-fridge, a microwave, and a Keurig duo (drip & pod) coffee maker.

Legoland Getaway 7 mins • Sleeps 7 • Elevator

Come relax with your family in this peaceful 2BR/2.5BA home, just 7 minutes from LEGOLAND®. Sleeps up to 7 guests, with pool access, board games, and arcade fun for all ages! Wheelchair accessible with elevator between floors. No parties, no smoking. Primary guest must be 25+ and present during stay; ID may be required.

Adorable 1 bed/1bath with office and free parking

This beautiful duplex is located in a Historic Bungalow built in the late 1920s, centrally located in Lakeland downtown. Nice park across the street for exercising or spending time with kids. Walgreens is one block away, and local bars, restaurants, antique stores, and lots of beautiful historic bungalows