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Lakeside Cottage on Lake Howard (Chain of Lakes)

The Lakeside Cottage sits on Lake Howard, one of the most popular locations on "The Chain of Lakes" near downtown Winter Haven. A lovely view of the lake and easy access to fishing, water sports and dining makes it a perfect spot for summer or winter. 1 bedroom, 1 bath plus a pull out couch in a large living room, large kitchen, lots of parking and on-site laundry in a comfortable 1949 home with lots of vintage appeal. Lake access is across the street but the lakeview is right out front. Enjoy!

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!

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!

Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn

This delightful lake-life inspired cottage includes 2 bedrooms and 1 ½ baths, a fooseball table, and easily sleeps 7 guests comfortably. Located just 15 minutes from Legoland and 45 minutes from Tampa & Orlando, this home is perfect for both families and those traveling for work. In fact, this Home is centrally located to dining, shopping, and small town fare. Come stay and enjoy downtown entertainment within walking distance (0.5 miles), or a quick car drive to Legoland (5.2 miles).

Lakefront Home on the Winter Haven Chain O’Lakes!

Completely renovated 2 Bedroom, 1.5 bath home location on beautiful Lake Roy on the Winter Haven Chain O’Lakes. One bedroom on the lower level with a queen bed. Second story with king bed and twin bed. Full bath located upstairs). Comfortably sleeps 5. (Additional guests must be pre-approved). Free boat parking and boat rental available. House is connected to the main home with a private keyless touchpad for contactless entry. Pet friendly with prior approval and pet deposit.

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!

Modern lakeside retreat by SEU and FSC

This 1920’s 1 bedroom 1 bath lakefront historic cottage is separate from the main house with its own entrance, parking, screened front porch, fire pit dock & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks, stand up paddle board, 4 seater pedal boat, and fishing poles and tackle are provided for your enjoyment. Come unwind and enjoy the lake views from the hammock and private beach!

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.

Lake View, Game Room, 10 min Legoland

Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor games designed w/ family fun in mind! Only 3 min to charming downtown Winter Haven shopping & restaurants, 10 min to Legoland, 30 min to historic downtown Lakeland, & conveniently located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa). We can't wait for you to enjoy the beautiful lakes of Winter Haven at The Elby!

Cozy 2-bedroom guesthouse on the lake

Enjoy a relaxing getaway on the beautiful Lake Ariana. Two bedrooms with queen beds comfortably accommodating four adults. Fully equipped kitchen and full bathroom with tub. Laundry room with washer and dryer. Private parking with plenty of room for boat or jet skis. Private entry with hosts on premises. Camera at exterior door for security. The guesthouse is behind the main home. There is not a view of the lake from inside the guesthouse.

5 - Life's a Beach Retreat 1bed/1bath - Unit 13

The 1-bedroom, 1-bathroom home features a fully equipped kitchen and covered front porch, making it the perfect spot to reel in a relaxing getaway. A cozy one-bedroom unit on the property of Cypress Inlet. Less than 10 minutes from LegoLand and Peppa Pig theme park. The property is on a canal that leads to Lake Eloise and the WH Chain of Lakes, and has boat ramp access and docks available; this vacation rental is an angler's paradise!