
Vacation rentals with lake access in Winter Haven
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Top-rated lake-access accommodations in Winter Haven
Guests agree: these lake-access accommodations are highly rated for location, cleanliness, and more.

Hidden 💎 Minimalist Design | Lego+Disney
Brand new, single family home with free parking. 4 Bed/2 Bath updated home with a large screened sun room. We made this home family-friendly because as parents ourselves, we know how nice that is! We even provided a baby crib. This home is light, breezy, comfortable, newly furnished and decorated; centered around a minimalistic vibe. Fully equipped, washer and dryer. Internet WiFi included. Close to Legoland (9 mi.), Disney (29 mi.), Golfing (6 mi.), and surrounded by beautiful lakes.

Lakefront, Dock, 2 Kayaks, near Bok & Legoland
** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

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!

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 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. 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.

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!

Breathtaking Home
New two story home with private pool, patio, barbecue area & game room. Surrounded by parks, gardens, tranquil lakes & walkways with breathtaking views. Resort amenities located right across the street with an amazing clubhouse (private owned), Bar & Grill restaurant, water park, arcade and gym (extra fee), soccer & football field, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

The Russell Lake House
This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

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.

Charming Lakeside Cottage
Escape to our cozy lakeside cottage, featuring a dock that’s perfect for watching sunrises, fishing, and launching your kayak. The property is on Lake Howard, which is part of the Winter Haven Chain of Lakes. Inside, you’ll find a fully equipped kitchen and comfortable living space for unwinding. Located just a short drive from the excitement of Legoland and Disney World, you can easily explore the area’s attractions while having a peaceful haven to return to.
Popular amenities for Winter Haven lake-access rentals
Lake-access house rentals

Clean Lakeland Home w/ Water Views & RV Parking!!!

Lake House by Legoland + Loft & Private Dock

Cozy Lakefront Home w/ Pool -7 mins from Legoland

Entire Vacation Home- Legoland

Hidden Gem - Hot Tub/ Fire pit/Hammock/Grill Area

Lakefront Getaway | Tiki Bar, Dock & Kayaks

Grammy's House on Lake Buckeye

Stylish Lakehome w.HUGE Pool/Arcade/Theater
Lake-access apartment rentals

King Bed Family Condo Orlando Disney Universal

Beach Heaven minutes from Disney

cozy house close to I4 monthly rental also

Top-Floor Lakeview Condo at Vista Cay Resort

2 bedrooms 2 baths near Disney Universal Seaworld

Oceanic Oasis Near Disney

2-Bedroom Renovated Lakeside Condo Near Disney

2B Condo Amazing Disney+Lake View from 2 Balconies
Lake-access cottage rentals

Lakefront Boho Cottage w/ Fire Pit | Still Waters

15min away from Disney- Family home and pool

Charming Lakefront Cottage Near Disney

3 - Lake Life House 1 bed/1bath - Unit 15

Cozy Historical Cottage

Cottage w/ Private Pool - Walk to Lake Wales!

Sunset Lake House

Entire house Close to Disney
When is the best time to visit Winter Haven?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $200 CAD | $208 CAD | $208 CAD | $179 CAD | $173 CAD | $169 CAD | $165 CAD | $160 CAD | $165 CAD | $171 CAD | $184 CAD | $190 CAD |
| Avg. temp | 16 °C | 18 °C | 20 °C | 22 °C | 25 °C | 27 °C | 28 °C | 28 °C | 27 °C | 24 °C | 20 °C | 17 °C |
Quick stats about vacation rentals with lake access in Winter Haven

Total vacation rentals
Explore 170 vacation rentals in Winter Haven

Nightly prices starting at
Winter Haven vacation rentals start at $28Â CAD per night before taxes and fees

Verified guest reviews
Over 7,380 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wifi availability
170 of Winter Haven vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winter Haven rentals

4.9 Average rating
Winter Haven stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with lake access Polk County
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- Rentals with lake access United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Raymond James Stadium
- Universal's Volcano Bay
- Busch Gardens Tampa Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Amalie Arena
- Tampa Convention Center
- Aquatica
- Disney's Hollywood Studios
- ICON Park





