
Waterfront holiday 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!

Waterfront Resort Condo near Disney &Universal
Located minutes from Disney World and Universal Studios you are right in the middle of all the action with Disney Springs, Islands of Adventure ,Sea World, Magic Kingdom,Epcot,two major outlet malls, and many other attractions .This resort style condo features a balcony overlooking beautiful Lake Bryan ,a beautiful pool that offers a full Tiki bar and food menu.Concierge services for Park tickets available. Free parking ,24hr security. Free HBO & Netflix . No deposit required and no extra fees.

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

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 (extra fee), arcade, gym, volleyball court, soccer & football fields, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

Top 1% Stay – Cozy Lakefront with Hand-Fed Swans
In the Heart of Lakeland, FL... on the Banks of Lake Morton! Nestled between the Historic District and beautiful South Lake Morton Historic District... (or as we like to call it, "Swan Lake") this property is located in easy walking distance to: Restaurants & Shopping Lakeland Public Library The Polk Museum of Art Historic Downtown Lakeland Lake Hollingsworth Florida Southern College Lake Mirror Hollis Gardens AND of course... Lake Morton Take it easy at this unique and tranquil getaway.

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.

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 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!
Popular amenities for waterfront rentals in Winter Haven
Waterfront apartment rentals

Magical Holiday+Relax+FreeParking

A Lake View Top Floor Condo! Sparkling & Modern

Lovely one bedroom apartment.

Renovated Studio-Near INT'L Drive and Parks!

Amazing Apartment in Orlando - Kissimmee

Brooks Edge - 1 BR/ 1 Bath with Home Office

Convenient and Close to All

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

Lake Whistler Beach House with lakefront pool

Mickey's Lakefront Villa at Sunset Lakes

Lakefront 4 Bed 3 Bath Private Home Free Spa Heat

3 bedroom Villa in Kissimmee

Beautiful Pool Home With Rear Conservation Views

Waterfront retreat,KING Bed,Heated Pool & Fire Pit

1157 5BD Dream Home Decoration - Champions Gate

"Cozy Retreat with something for everyone"
Waterfront apartment rentals

3161-305 Resort Lake View Disney Universal Orlando

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

303_To Infinity & the Ocean Breeze Apartment

Modern Lake view Condo 1 mile from Disney

Chic Disney Resort Condo • Pool Access Near Parks

A Resort Getaway with many amenities

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

Island Style at Bahama Bay - Minutes 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 | £111 | £126 | £128 | £125 | £110 | £103 | £103 | £107 | £103 | £116 | £116 | £114 |
| 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 holiday rentals
Explore 90 holiday rentals in Winter Haven

Nightly prices starting at
Winter Haven holiday rentals start at £30 per night before taxes and fees

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

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
90 of Winter Haven holiday 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!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Saint Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Rentals with a hot tub Winter Haven
- Apartment rentals Winter Haven
- Villa rentals Winter Haven
- Private suite rentals Winter Haven
- Hotel rooms Winter Haven
- Guest house rentals Winter Haven
- Fitness-friendly rentals Winter Haven
- Cottage rentals Winter Haven
- Rentals with lake access Winter Haven
- Flat rentals Winter Haven
- Pet-friendly rentals Winter Haven
- Rentals with pools Winter Haven
- Rentals with a washing machine and dryer Winter Haven
- Family-friendly rentals Winter Haven
- House rentals Winter Haven
- Cabin rentals Winter Haven
- Rentals with a fireplace Winter Haven
- Rentals with a firepit Winter Haven
- Rentals with a patio Winter Haven
- Rentals with a kayak Winter Haven
- Rentals with breakfast Winter Haven
- Rentals with outdoor seating Winter Haven
- Waterfront rentals Polk County
- Waterfront rentals Florida
- Waterfront rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Walt Disney World Resort Golf
- 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




