Best Accommodations in Winter-Haven

Groovy Funhouse Getaway - 4 bdrm near Legoland is a recently renovated vacation home in Winter Haven where guests can make the most of its outdoor swimming pool, garden, and barbecue facilities. This property offers access to a terrace, a pool table, free private parking, and free Wifi. Outdoor seating is also available at the vacation home. The air-conditioned vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and a hair dryer. Towels and bed linen are offered in the vacation home. This vacation home is allergy-free and non-smoking. For guests with children, Groovy Funhouse Getaway - 4 bdrm near Legoland offers kids pool and an indoor play area. Phosmico Railroad Station (Historical) is 7 miles from the accommodation, while Swanns Railroad Station (Historical) is 8.1 miles from the property. Tampa International Airport is 50 miles away.

Parking • Other • Child Friendly • Ocean View • Fireplace/Heating • Pool • Security/Safety • Oceanfront • Air Conditioner • Guest Services • View • Internet

Close to theme parks, outlet shopping, and more, this welcoming vacation home brings it all within reach. Jump into your car and make short work of the 14-minute drive to LEGOLAND® Florida or the 7-minute drive to Sertoma Park (and enjoy the property's convenient onsite parking in the meantime).

After you return, unwind in the outdoor entertainment area or sip a drink in the garden, and don't forget about the outdoor furniture. As for the great indoors, you can come inside and enjoy the free WiFi and digital TV.

Premium bedding, a charcoal grill, air conditioning, and blackout drapes/curtains are featured at this 1-bedroom rental. Bathroom amenities include free toiletries, towels, and toilet paper. And there's access to laundry facilities, so you can even pack a bit lighter.

Toiletries • Laundry • Balcony/Terrace • Child Friendly • Internet • Entertainment • Sports/Activities • Air Conditioner • Barbecue/Outdoor Cooking • Other • Parking • Bedding/Linens

Lakeside Lofts at Lake Martha offers accommodations in Winter Haven, 4.5 miles from Legoland Florida and 10 miles from Phosmico Railroad Station (Historical). The air-conditioned accommodation is 3.1 miles from Swanns Railroad Station (Historical). There's a sun terrace and guests can use free Wifi and free private parking. Featuring a patio and lake views, the spacious villa includes 4 bedrooms, a living room, flat-screen TV, an equipped kitchen, and 2 bathrooms with a bath and a shower. Towels and bed linen are offered in the villa. There's also a seating area and a fireplace. Carters Railroad Station is 11 miles from the villa, while Conshul Railroad Station is 11 miles from the property. Orlando International Airport is 47 miles away.

- "The best in the area!" - "Class and Comfort, High Quality, Great Location, Very Clean, Family Friendly !!!!" - "Great place close to legoland, would stay again" - "Great view with a cozy vibe" - "Would stay again and recommend staying.. close to Legoland for our stay" - "Great value and location for Legoland" - "Overall, great stay and worth it."

1 bedroom, 1.5 bath In-law Guest Suite with private entrance in safe, quiet neighborhood in the Cypress Gardens area of Winter Haven, only 1.2 miles from Legoland. Although attached to main house, this in-law unit is totally separate from it and includes a king bed, bunk beds, sofa sleeper, and kitchenette with fridge, microwave, air fryer, Instapot, and induction cooktop for light cooking. Full bath is attached to main living area and bedroom has private half bath. Separate desk with MFC printer. 2 TVs include popular streaming services. Sleeps up to 5. Parking space reserved for guests in driveway. Private screened patio too! **If you are booking this through Expedia, note that your check-in instructions will come from VRBO, not Expedia, a few days before your stay begins.**

- "So clean and cute! Lots of nice little details and the king-size bed was super comfortable. Having an extra half bath means my partner could shower while I was getting ready too. Even though we shared walls with the main house, it was quiet and felt very private. " - "It was the perfect place to crash after spending the day visiting my dad. Easy to access the main roads. The bed was super comfy and we streamed some TV in the evenings. "

Stylish-N-Private 1BR Retreat 2 Miles to LegoLand offers accommodations in Winter Haven, 11 miles from Phosmico Railroad Station (Historical) and 12 miles from Conshul Railroad Station. With free private parking, the property is 1.9 miles from Legoland Florida and 7.1 miles from Swanns Railroad Station (Historical). Dearborn Railroad Station is 13 miles from the vacation home and Tanco Railroad Station is 14 miles away. The accommodation is non-smoking. Carters Railroad Station is 16 miles from the vacation home, while Elmer Railroad Station is 18 miles away. Lakeland Linder International Airport is 22 miles from the property.

- "The hosts were amazing very attentive and even answered at 11:30 pm" - "Very spacious and clean place." - "Great location. Would definitely stay again." - "Bring an air mattress and fan"

Nestled within the heart of Winter Haven, Chain of Lakes Cottage offers an enchanting retreat that celebrates the beauty of the interconnected chain of lakes in the region. This elegantly designed cottage is a haven for those seeking tranquility, stunning views, and a touch of luxury.

Travel to local attractions:
- 5 minutes to Winter Haven Hospital
- 7 minutes to AdventHealth Fieldhouse
- 9 minutes to Diamondplex Softball Complex
- 15 minutes to Lake Myrtle Sports Park
- 15 minutes to Legoland
- 30 minutes to Sun N Fun Aerospace Expo
- 30 minutes to Lakeland Regional Medical Center
- 35 minutes to Bok Tower
- 45 minutes to Magic Kingdom/EPCOT/Animal Kingdom
- 60 minutes to Orlando International Airport
- 60 minutes to Tampa International Airport

This elegantly designed cottage is a haven for those seeking tranquility with a touch of luxury. Offering a family-friendly environment, the Cottage is complemented with pet-friendly features; fenced in yard, ample space and lush landscaping for privacy.

Property offers guests all the amenities needed to enjoy their stay.
- Fully stocked kitchen for cooking and baking
- Onsite washer and dryer
- Oversized bedrooms with king beds
- Fenced backyard for kid and pet enjoyment
- Lush landscaping for privacy
- Quiet neighborhood

- "Everything was spotless, fresh,bright and cheerful. Perfect yard for dog ! "

Hook, Line and Leisure Lakefront Gem with Porch! is located in Winter Haven, just 9.4 miles from Carters Railroad Station and 11 miles from Phosmico Railroad Station (Historical). The air-conditioned accommodation is 5.9 miles from Legoland Florida. Free Wifi is available throughout the property and Swanns Railroad Station (Historical) is 1.5 miles away. Offering a patio and lake views, the spacious vacation home includes 3 bedrooms, 2 living rooms, cable flat-screen TV, an equipped kitchen, and 3 bathrooms with a bath and a shower. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Elmer Railroad Station is 11 miles from the vacation home, while Allied Railroad Station is 11 miles from the property. Orlando International Airport is 45 miles away.

- "A great stay in a beautiful home. Perfect place for a family of 4 or 5. Everyone had enough room to be very comfortabl" - "It was a great home very peaceful" - "Beautiful and spacious home to relax in and enjoy family time." - "There was not enough time to enjoy this spectacular home." - "Very clean home with ample space for a large family." - "Nice house, wishing for a better location and better AC."

Private Guest House wt Pool Close to Legoland! Only 3 miles from Legoland, 30 miles from Disney, and 2 miles from Chain of Lakes Boat Access (Lake Summit).

Enjoy a family friendly vacation at our guest house! Self check in with private entrance. The property is a duplex style house. The property has a tenant on one side of the house (separate entrance). Tenant does NOT use outdoor amenities. Amenities are for guests only. There are NO shared spaces.

- "Accurate pictures and descriptions of the property! Super cute and cozy little place. Would be perfect for summer time getaways! Conveniently located close to everything you need but the privacy and Peacefulness of being out of the city. Will definitely stay here again if available when come back to the area. "

Winter Haven Home with Pool Near Legoland! offers accommodations in Winter Haven, 2.8 miles from Legoland Florida and 5.3 miles from Swanns Railroad Station (Historical). This vacation home features air-conditioned accommodations with a patio and free Wifi. Dearborn Railroad Station is 11 miles away and Tanco Railroad Station is 13 miles from the vacation home. Featuring a terrace and garden views, the spacious vacation home includes 3 bedrooms, 2 living rooms, flat-screen TV, an equipped kitchen, and 2 bathrooms with a shower. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Guests can enjoy the outdoor swimming pool and garden at the vacation home. Phosmico Railroad Station (Historical) is 8.8 miles from Winter Haven Home with Pool Near Legoland!, while Conshul Railroad Station is 10 miles from the property. Orlando International Airport is 48 miles away.

Fireplace/Heating • Pet Friendly • Security/Safety • Balcony/Terrace • Guest Services • Child Friendly • Other • Internet • View • Pool • Accessibility • Parking

Super comfortable!
Modern clean fully functioning. centrally located in Winter Haven. 1/2 mile to downtown, less than 4 miles to Legoland. every shopping need and many great dining choices all within a mile of the house.

Your own driveway, patio, private studio, and bath.

Your own driveway, private patio, and private entry. This Studio apt. is on the right side of a duplex. We live in the other half of the duplex but your side is totally private, with its own central heat & air.

You alone will have access to your patio, unit, and bathroom.

Nice quiet safe friendly neighborhood close to everything.

Self-check in after 3 pm. You will use the code given for the lock keypad.
We have taken pleasure in making sure the home we provide has the listed amenities available, is clean, and is well maintained. Although we do a thorough professional clean between each guest stay, we kindly ask that before leaving, you clean and put away any dishes or kitchenware used and any dirty towels in the hamper. Also, please report any malfunctioning appliances or issues to us right away. The house is very comfortable, and we hope you love it as much as we do. We want to emphasize that there is to be absolutely NO SMOKING in the home. Also, cooking with strong-smelling spices or deep frying is prohibited. Guests have done this in the past and it has taken nearly three days to remove the strong odors from the house, even with our professional cleaning. If the home is found to have a pungent smell from cooking or smoking following your stay, we will need to impose a $300 fine. If it is found that you have more guests staying the night than has been booked, you may be requested to leave the property without a refund.

- "Cool little place, love the outdoor private patio.Very close to everything downtown"

Spacious 4-bedroom 2-bath Abode is located in Winter Haven, just 7.7 miles from Legoland Florida and 7.9 miles from Phosmico Railroad Station (Historical). The air-conditioned accommodation is 7.1 miles from Swanns Railroad Station (Historical), and guests can benefit from on-site private parking and complimentary Wifi. Carters Railroad Station is 10 miles from the vacation home and Elmer Railroad Station is 12 miles away. Offering a patio, this vacation home also features a cable flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a bath and a hair dryer. The property has an outdoor dining area. Guests can relax in the garden at the property. Conshul Railroad Station is 9.2 miles from the vacation home, while Dearborn Railroad Station is 10 miles from the property. Orlando International Airport is 50 miles away.

- "Family vacation/ proposal" - "We were in town to take my son to Lego Land and it was a perfect spot." - "Good Deal For Two Families" - "Enjoyed the stay" - "It was okay, but I won’t return." - "Good place to stay for our softball tourney; great host."

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a garden.

Internet • Child Friendly • Balcony/Terrace • Other

Getaway Clubhouse is located in Winter Haven, just 4.3 miles from Legoland Florida and 8.7 miles from Phosmico Railroad Station (Historical). This vacation home offers accommodations with a balcony. Free Wifi is available throughout the property and Swanns Railroad Station (Historical) is 3.5 miles away. The air-conditioned vacation home consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a kettle, and 3 bathrooms with a bath and a hair dryer. A TV is featured. The accommodation is non-smoking. Guests can also relax in the garden. Conshul Railroad Station is 10 miles from the vacation home, while Carters Railroad Station is 11 miles away. Lakeland Linder International Airport is 19 miles from the property.

- "Very nice place. Clean and close to Legoland."

This is a unique 2 story antique building that has been completely renovated into 4 small apartments. This property was designed with the porpoise of offering our guest an oasis of peace, tranquility; geared towards meditation and relaxation. Though we are located only few minutes from restaurants, stores, hospitals, universities and much more, once you turn into our street, you will notice the quiet and serine atmosphere of the neighborhood.

- "Had everything we needed, small but very nice and clean." - "This was my second stay with Gladys, and other than one small hiccup, it was just perfect. The door code didn't work upon arrival, but it was quickly remedied, and Jullianna even came out to check on me. I plan on staying here every time I come to visit." - "The property was very clean and well maintained. The host responded promptly to questions. The overall stay was great. The only drawback was the listing was misleading as far as a washer/dryer. There was one on the property, but you had to schedule ahead to use it and there was an additional fee. Otherwise great place!!!"

BlockHaven near Legoland, Disney is a recently renovated vacation home in Winter Haven where guests can make the most of the garden and barbecue facilities. This property offers access to a patio, a pool table, free private parking, and free Wifi. Dearborn Railroad Station is 7.4 miles from the vacation home and Legoland Florida is 8.6 miles away. Providing a terrace and garden views, the spacious vacation home includes 3 bedrooms, a living room, satellite flat-screen TV, an equipped kitchen, and 1 bathroom with a bath. Guests can take in the ambience of the surroundings from an outdoor dining area. The vacation home offers bed linen, towels, and laundry service. An indoor play area is also available for guests at the vacation home. Phosmico Railroad Station (Historical) is 5.1 miles from BlockHaven near Legoland, Disney, while Conshul Railroad Station is 6.4 miles away. Lakeland Linder International Airport is 15 miles from the property.

- "100% recommended"

This studio is located minutes from Downtown Winter Haven, one of Florida's oldest towns. The small downtown is packed with lots of unique delightful places where you can eat and drink. It’s also a perfect place just to walk around and have a relaxing evening. Its a place you must experience at night!

- "Love it!" - "Location is near food, gas, and antique shops. The town closes at 6pm. Very clean has everything u need. Loved the shower! No weird smells or loud partygoers." - "I spent four days here and I were would return. The room was as described and very clean" - "fun 😻" - "We had a nice stay - everything we needed, was provided." - "Great honey place to stay while in town for work." - "I definitely can not wait to return to this property✨loved all the small details and thoughtfulness! Incredible time! The only little thing that I can mention is the door keypad, in the middle of the night 2-3 times it made a clicking noise, not sure how come. The bed made it easy to fall back asleep though 😴"

Lanai and Pool Elegant Villa in Winter Haven! offers accommodations in Winter Haven, 3.3 miles from Swanns Railroad Station (Historical) and 6.4 miles from Legoland Florida. This beachfront property offers access to a balcony and free Wifi. Carters Railroad Station is 8.5 miles away and Phosmico Railroad Station (Historical) is 10 miles from the villa. Offering a terrace and lake views, the spacious villa includes 4 bedrooms, 3 living rooms, cable flat-screen TV, an equipped kitchen, and 5 bathrooms with a bath and a shower. Towels and bed linen are offered in the villa. The property has an outdoor dining area. Guests can enjoy the outdoor swimming pool and garden at the villa. Elmer Railroad Station is 10 miles from Lanai and Pool Elegant Villa in Winter Haven!, while Allied Railroad Station is 10 miles from the property. Lakeland Linder International Airport is 19 miles away.

- "Extraordinary weekend in a luxurious home. The owner Tom is very hospitable and cares deeply about his guest" - "Nice cosy house for a couple of days stay" - "Loved it!"

Welcome to Sunrise on Lake Idylwild

Your perfect lakeside getaway awaits on the beautiful Chain of Lakes in Winter Haven, Florida!



This thoughtfully designed and tastefully decorated lakefront home offers something special for everyone in your group—whether you're planning a family vacation, a relaxing retreat, or a mix of both. Situated on scenic Lake Idylwild, this home features a private dock and connects to 18 other lakes in the chain, opening up endless opportunities for water adventures.



Bring your boat or jet skis—there’s a public boat ramp just under a mile away at Lake Cannon Public Park. We also provide two kayaks—including one specially outfitted for fishing. From the dock, you can explore the lakes, fish, visit waterfront restaurants and bars, or even boat directly to Legoland for the iconic Cypress Gardens ski show. Need a boat rental? We’re happy to offer recommendations.



Inside, the home feels like a coastal model home, featuring:



3 bedrooms, study & 2 full baths



A beautifully updated primary suite with king bed, en suite bath & walk-in shower



A queen guest room across from the second full bathroom



A family-friendly bedroom with two twin beds, changing table & Futon



A dedicated study with a queen Murphy bed that doubles as a desk when bed not in use & storage cabinet



The gourmet kitchen is fully equipped for preparing meals at home, and the spacious dining table seats 10 under a handcrafted, charming light fixture. Outside, enjoy a BBQ with the propane grill, or unwind with a drink on the dock as boats pass by.



The enclosed Florida sunroom brings the fun indoors with:



Pool table



Foosball



Outdoor-style lounge seating



Tiki bar



Vizio Smart TV for entertainment



Outdoor Amenities Include:



Private dock with seating for 2



Great fishing and boating opportunities right from the backyard



2 Kayaks for guest use & life jackets



Jungle gym for children with swings, slide & climbing wall



Indoor Amenities:



Free Wi-Fi



62” Vizio Smart TV in the living room



Smart TVs in all bedrooms (no cable)



Coffee bar with Keurig & drip coffee maker



Fully stocked kitchen with dishes, cookware, toaster, microwave



Washer & dryer



Iron & ironing board



Linens & towels provided



Nearby Attractions:



8 minutes to Downtown Winter Haven



7.5 miles to Legoland



About an hour’s drive to Disney World, Universal, SeaWorld, and Busch Gardens



Safety & Security:



Remote keyless entry with deadbolt



Smoke detectors & fire extinguisher



NOTE: Please be advised: For your safety and security, exterior video surveillance (driveway & front porch) and exterior video on the boat are in use. Tampering is prohibited.

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Book your stay today with confidence! We are iTrip - Lakes of Central Florida; a professional short-term rental property management company in central Florida. We have hosted over 3000 great stays with an average guest review score of 4.9 out of 5!



Extended Stays - Any reservation exceeding 30 nights will be required to pay an additional cleaning fee each month that the stay extends. Cleaning will be coordinated with the management team. The additional cost will be added to your reservation after confirmation.

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- "Fantastic property, quiet and great location for Legoland and bass fishing on the lakes which was our main aim. Also not too far from other theme parks and golf courses. Everything well set up in the house for our arrival and the grand kids loved the games room!!" - "Amazing stay !!!" - "We really enjoyed our stay at this lake house. It was a great location and we used it as a staging area to move our son into FSC dorms. Close to grocery shopping and some decent restaurants. My son was able to catch a fair amount of bass right from the dock. Oh and the AC unit in the sun room was a game changer since it was so hot outside. Will likely stay here again when we come to visit our son."

Historic home lake access, near parks and venues is a recently renovated vacation home in Winter Haven where guests can make the most of its garden and terrace. With garden views, this accommodation offers a patio. The vacation home provides rooms with air conditioning, free private parking, and free Wifi. The vacation home provides guests with a balcony, lake views, a seating area, cable flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, and a private bathroom with bath and a hair dryer. A microwave, a toaster, and fridge are also provided, as well as a coffee machine. At the vacation home, all units come with bed linen and towels. Guests can make the most of the warm weather with the property's barbecue facilities. The vacation home has a picnic area where you can spend the day outdoors. Swanns Railroad Station (Historical) is 2.2 miles from Historic home lake access, near parks and venues, while Legoland Florida is 5.4 miles away. Orlando International Airport is 45 miles from the property.

Air Conditioner • Parking • View • Fireplace/Heating • Guest Services • Balcony/Terrace • Other • Sports/Activities • Smoking • Security/Safety • Barbecue/Outdoor Cooking • Internet

Waterfront Patio | Sunset Views | Voted 3rd Best Staycation in Winter Haven | ~1 Mi to Legoland

Situated on an idyllic peninsula surrounded by the waters of Lake Eloise on the Winter Haven Chain of 14 lakes, this 1-bath studio vacation rental offers a dreamy waterfront getaway! With an updated interior, outdoor kitchen, and fire pit with sunset views, the cottage is perfect for a staycation, for couples to celebrate special occasions, or for those who enjoy boating, birdwatching, and fishing.

-- THE PROPERTY --

SLEEPING ARRANGEMENTS
- Studio: 1 queen bed, 1 queen sleeper sofa

INDOOR LIVING
- Smart TV, books/board games
- Dining table
- Dedicated office space

OUTDOOR LIVING
- Covered deck
- Indoor/outdoor bar w/ seating
- Hot tub, fire pit
- Lounge area
- Covered patio w/ Blackstone grill & sink

KITCHEN
- Refrigerator, microwave, dishwasher, stove/oven
- Coffee/latte/cappuccino maker, toaster, blender, slow cooker
- Cooking basics, dishware/flatware

GENERAL
- Free WiFi
- Washer & dryer
- Central A/C & heating, ceiling fans
- Linens & towels, trash bags & paper towels
- Hair dryer, iron/board

FAQ
- Homeowner on-site (separate unit)
- No fence before water

ACCESSIBILITY
- Single-story studio, 1 step required to enter

PARKING
- Shared driveway (3 vehicles)
- RV/trailer parking available on-site

-- THE LOCATION --

- Centrally located near many popular Florida attractions
- On-site access to Winter Haven Chain of Lakes - 16 connected lakes via navigable canals
- 4 miles to Lake Bess Golf Club, 5 miles to Lake Ashton Golf Club, 10 miles to Willowbrook Golf Course
- 6 miles to Downtown Winter Haven
- 31 miles to Walt Disney World, 43 miles to Universal Studios, 54 miles to Busch Gardens
- 50 miles to Orlando International Airport, 60 miles to Tampa International Airport

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking or vaping of any kind
- No pets allowed
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in

ADDITIONAL INFORMATION
- This single-story unit requires 1 exterior step to access
- The homeowner lives on-site, in a completely separate unit, and may be present during your stay
- The home does not have a fence before the water and may not be suitable for young children
- If you are flying, we suggest flying into Tampa International Airport as the roads and traffic in Orlando are very heavy

- "The home is as advertised. Everything was clean and the host was very helpful. The view of the lake is wonderful. Would definitely stay here again if needed." - "It was peaceful and felt like I was still at home with how comforting our host was. This was my favorite rental property I’ve ever experienced " - "We found a little piece of paradise on the shores of lake Eloise. Surrounded by old cypress trees, the cottage sits tucked away on its own little peninsula which lends to a feeling of seclusion and privacy while still in the middle of everything that is central Florida. Very clean and well furnished. Friendly and helpful hosts. The sunsets over the lake were amazing. We loved everything about this place and we will definitely be back!"