Pet-friendly vacation rentals in Winter Haven

Charming, renovated 1917 Cottage

Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!

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.

Florida Oasis w/ Pool near LEGOLAND

We have added a modern twist to the design of this 1950's home with all the modern appliances and finishes. This home is nestled in-between 2 lakes among the Winter Haven Chain of Lakes! The backyard is a Florida Oasis of a great pool and pool deck with plenty of fun available with games for you and the kids, or just enjoy laying peacefully in the sun! 2.5 mile drive from Legoland 3.5 mile drive from Downtown Winter Haven with great restaurants and small town unique shops.

Hollingsworth Pool Home

This artistic, craftsman-style pool home is regally situated on a red brick street in Lakeland's beloved Lake Morton Historic District. Centrally located, with Lake Hollingsworth just 2 blocks away, the Hollingsworth House is also walking distance to Cob & Pen, Concord Coffee, and the trendy Dixieland neighborhood where you can shop at antique and boutique shops. The large pool is surrounded by 8 foot privacy fence and a fully-fenced in backyard. Free driveway parking.

Legoland Lakehouse w/Pool &New AC

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!

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!

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 10 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.

Winter Villa in Florida by the Lakes

Relax with your whole family at this peaceful haven which boasts a backyard view to golf course and pond and easy access to local boat docks and fishing. You can also get to Disney, Universal Studios and other Kissimmee attractions in minutes. The community offers a gated pool and quiet neighbors that make you feel welcomed.