
Waterfront vacation rentals in Winter Haven
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Winter Haven
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

6 - Just Beachin' Cabin 2bed/2bath - Unit 10
Experience the tranquility of the Sunshine State from this quaint-yet-modern vacation rental home, complete with 2 bedrooms, 2 bathrooms, a private deck, and modern interior finishes. You’ll enjoy direct access to a boat launch and the Chain of Lakes, a fishing and boating paradise complete with 24 canal-connected lakes! Spend your days out on the water, make incredible memories with your family at LEGOLAND Florida, or opt to visit the theme parks in Orlando - from this home, you can do it all!

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

2 Bedroom Winter Haven Guest Suite
Private lock-off unit. Only shared between your party. Attached to main home , no shared spaces inside. 1st bedroom -Queen bed and sitting area bathroom attached. 2nd bedroom- two twin sized beds Kitchen and living room included and not shared outside of your party. 3 minutes from Winter Haven hospital. Self check in and out. 20 minutes from Legoland. 45 minutes from Disney and Universal This is an older florida neighborhood with a diverse and working class vibe. Located on Lake Maude

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!

Ground Floor Oasis you will never forget
Private large 3-bed ground floor Villa with a king-size bed in the master bedroom and ensuite. Includes free parking out front. Full kitchen with breakfast bar, 2 full baths, living and dining areas, and 2x balcony. Full Wifi, TVs in all rooms. Full accommodations include a gym, restaurants, and bar areas, 4 large heated pools with a beach, and multiple hot tubs—minutes from Disney, restaurants, and more. In-suite laundry and house cleaning are available—24-hour security, gated property.

Sand Lake Villa Townhouse by Universal & Disney
Chic Boho-Modern 2BR Lakeside Townhome! Unwind with loved ones & explore the best of Dr. Phillips—steps from Orlando’s top dining on Restaurant Row, plus I-Drive, Disney, Universal, SeaWorld, Whole Foods, Trader Joe’s, Publix, Target & Walmart all within 6 miles! Features a Queen bed on the first floor & 2 Queen beds upstairs. Sip your morning coffee by the peaceful lake before your adventure begins. Perfect for family vacations or work trips—we’d love to host your next Orlando stay!

Beautiful Lake House Boating Fishing near Legoland
Welcome to The Executive Lake House ten minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers two bedrooms, a , full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is ( not) included at this price point. If wanting an additional charge of 20 dollars per night Will be charged. Let me know at booking.

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!

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 Lakeside Splash 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!
Popular amenities for Winter Haven waterfront rentals
Waterfront apartment rentals

*Value Stay* Private and Cozy Waterfront 1b1b Apt

Magical Holiday+Relax+FreeParking

Lovely one bedroom apartment.

WATER View 4BR/Elevator/DISNEY Area

Renovated Studio-Near INT'L Drive and Parks!

Spacious Modern Penthouse

Amazing Apartment in Orlando - Kissimmee

★BRAND NEW APT with LAKEVIEW - Close to Disney★
Waterfront house rentals

Lakeside Bungalow - Winter Haven Chain-of- Lakes

Lakefront 4 Bed 3 Bath Private Home Free Spa Heat

3 bedroom Villa in Kissimmee

Private Ranch Style Home on Lake

Beautiful Pool Home With Rear Conservation Views

Southern Dunes Lakeview Poolhome

"Cozy Retreat with something for everyone"

Private lake front retreat!
Waterfront condo rentals

Welcome to our Son Shine condo ....

Location,Location 3bd 2bth near parks conv.ct/Int.

Chic Disney Resort Condo • Pool Access Near Parks

Themed Resort Condo-Pool | Spa | Beach | 1st Floor

Poolside 3Br~Windsor Hills~Waterpark~2mi to Disney

[Lake View, Modern Decor, 1 Mile to Disney!]

Island Style at Bahama Bay - Minutes to Disney!

Lakefront Resort Condo near Disney and Universal
When is the best time to visit Winter Haven?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 126 | € 142 | € 145 | € 141 | € 124 | € 116 | € 116 | € 121 | € 116 | € 131 | € 131 | € 129 |
| 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 waterfront rentals in Winter Haven

Total vacation rentals
Explore 90 vacation rentals in Winter Haven

Nightly prices starting at
Winter Haven vacation rentals start at € 34 per night before taxes and fees

Verified guest reviews
Over 6,240 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
90 of Winter Haven vacation rentals include wi-fi 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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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- Disney Springs
- SeaWorld Orlando
- Disney's Animal Kingdom Theme Park
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Old Town Kissimmee
- Raymond James Stadium
- Walt Disney World Resort Golf
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Aquatica
- Amalie Arena
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ZooTampa at Lowry Park




