Vacation rentals with a firepit in Winter Haven

Adult-Only Getaway w/ Mermaid Pool | 18+, Private

🔒⛓️🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

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, Historic District Home - GREAT LOCATION

Enjoy a stylish experience at this centrally-located place 5 mins from downtown Lakeland, 8 mins from I-4, 40 mins from Tampa and Orlando (Disney World/Universal), 1 hour from several beaches including Clearwater. 🐕 Pet friendly but you MUST include your pets in the reservation Nearby places of interest: - Downtown Lakeland - Southeastern University and Florida Southern College - RP Funding Center - Lakeland Linder International Airport - Polk Theatre - Circle B Nature Reserve - and more!

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. The dock has plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door. Please note there is no barrier around pool and all children (anyone under age of 18)must be supervised at all times. Guests must swim at their own risk. You may see horses in the paddocks. The pool deck overlooks the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

Magical Pool Villa-close to Disney Game/movie Room

The magic starts the moment you walk through the door—and the memories will last a lifetime! ✨ Our themed vacation home features Mickey Mouse, Toy Story, Frozen, Star Wars and Minion rooms with motion-activated songs, UV artwork, and LED lighting. Enjoy a private pool with color-changing lights, BBQ area, sun loungers, and a fun-filled game room with air hockey and arcade games. Designed to delight kids and adults alike with immersive sights, sounds, and magical details throughout the home!

Bamboo Bus -Sauna/Pool/Fire pit/Grill

Bamboo Bus is a unique, romantic and tranquil spa like getaway, perfect for relaxing with your significant other, family or friends. Enjoy the pool, unwind in the barrel sauna, grill your favorite meals and gather around the fire pit for s’mores under the stars. Located less than a mile from Lake Pierce, bring your kayaks and explore nearby lakes and state parks. Just 20 mins to LEGOLAND and 50 mins to Disney, it’s the perfect peaceful escape with easy access to Central Florida attractions.

Extra large home! Bring Your Boat & all the Toys!

Bring your boat, skis, fishin’ pole, or any other water toys! We supply ping pong, corn hole, bicycles and other toys! Directly across from Lake Howard boat ramp and 10 minutes from LegoLand! Enjoy this spacious, well-equipped 2300 sf home that has everything you need to enjoy your stay in Winter Haven, aka Chain of Lakes City, a quaint downtown with free parking-- and just a skip away from Disney and Universal. This getaway is an above-average accommodation both in style and comfort!

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

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).

Classic Cottage in country setting

Relax with the family in this peaceful setting. Short drive to the parks, shopping, restaurants. 10 minutes from Interstate 4. Walmart and Posner Park Shopping Center nearby. Patio area with fire pit and gas grill and lawn chairs. 2 car carport parking on premise. 2 bedroom w/HDTV's, 2 bath, fully furnished kitchen, dishwasher, breakfast nook, dining room, living room w/HDTV. Washer/dryer. Fully fenced 3/4 acre yard with plenty of room for kids to play. Self check in with keypad.

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. This is a mother-in-law suite that is connected to the main home. 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. Dog welcome with prior approval and pet fee. Boat parking at dock. Boat rental available at Central Florida Water Sports. Private entry with keyless touchpad.

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.

2 - Ships Ahoy Bungalow 2 bed/2 bath - Unit 17

Florida’s lakes and biggest attractions are calling you and your family to stay at this vacation rental in Winter Haven! From Legoland and Disney World to the famous Chain of Lakes and golf courses galore, this charming home in Cypress Inlet is minutes from it all. Take your boat out on Lake Eloise, through a private canal right outside the home, or take the kiddos to SeaWorld, a short drive away, before returning to this 2-bedroom 2-bath home.