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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.

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Townhouse in Kissimmee

4.83 out of 5 average rating, 168 reviews

NEW Vacation Home in Storey Lake Resort, Disney!!!

NEW & MODERN HOME with lake view. NEAR DISNEY! Located in the new Storey Lake condominium in Kissimmee, just minutes from the Walt Disney World and within walking distance to shopping, dining, and other local activities. Beautiful townhouse with 5 bedrooms and 4 bathrooms offers great comfort and modern decor with Smart 4k TVs in all bedrooms and living room, private pool, free Wi-Fi, dishwasher, washer and dryer, iron, ironing board, hair dryer and access to the fabulous Storey Lake Clubhouse

Cottage in Winter Haven

4.82 out of 5 average rating, 134 reviews

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!

Home in Winter Haven

4.99 out of 5 average rating, 113 reviews

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 loft , full kitchen and laundry and one full bathroom. The 1100 square foot space which offers 12 foot ceilings and unique interior design will leave you amazed. If your looking for more than a space to sleep but a place to vacation than this is It.

Home in Winter Haven

4.91 out of 5 average rating, 303 reviews

💎3/2💎SpeciouS☀Modern🎢4Miles-LEGOLAND🎢

WELCOME to our Lake Mariam Vacation Home (2), duplex on 3 acres of Lakefront property. We are a family own business & genuinely hope to tailor our properties to meet our Guest needs. We adhere to a 3 Core Property Standards that we expect; so, you'll always arrive to a home that is Safe, Clean and Guest Ready! This property is centrally located, 2 mi to dtwn Winter Haven and the Hospital & 4 mi to LEGOLAND & Peppa Pig. Orlando attractions (SeaWorld, Disney/Universal) are all w/in an hr. drive!

Villa in Lake Wales

4.98 out of 5 average rating, 190 reviews

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

Condo in Orlando

4.86 out of 5 average rating, 146 reviews

Welcome to this Blue Heron Beach Beauty.

Great condo location close to Disney. Recently updated. Shuttles to theme parks. Departure times from Resort: Epcot: 8:20am, 10:50am $10 per person round trip. Sea World: 9:30am, 11:05am, 12:00pm $10 per person round trip. Universal: 9:30am, 11:05am, 12:00 pm $12/PP/USD charge for the shuttle to Universal. SHUTTLE SERVICE IS SUBJECT TO CHANGES. Return times: Epcot: 6:20pm, 8:30pm, 10:30pm Sea World: 5:30pm, 6:30pm Universal: 7:15pm $12/PP/USD charge for the shuttle to Universal.

Rental unit in Clermont

4.82 out of 5 average rating, 247 reviews

Charming Lakefront Apt. Near Disney

Unique 1,100 sq. ft apartment located in South Clermont, less than 25 minutes to Downtown Orlando, Walt Disney World, and all Central Florida attractions. Lake Sawgrass is available for fishing, kayaking, boating, and other watersports activities. Our location is quiet and peaceful located in the countryside. We are located on the newly paved Schofield Road, with less than 1-mile of dirt road now on Cook Road. The unit is on well water, with water softening and filtration installed.

Home in Kissimmee

4.89 out of 5 average rating, 102 reviews

Peaceful Waterfront Retreat, Close to Everything!

Beautiful 4br peaceful lakefront home in safe, quiet community. Close to major shopping and restaurants! Just a short drive to the Turnpike and 417 highway, close to Disney, Seaworld, Medical City, Lake Nona and the VA Hospital. Comfortable space with smart TVs and central AC. Fully equipped kitchen. Split floor plan perfect for families and friends. The master bedroom faces the rear of the home, large windows allowing natural light to enter the home all while enjoying your waterview!

Home in Clermont

4.93 out of 5 average rating, 199 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow full disinfecting of the house.

Rental unit in Auburndale

4.95 out of 5 average rating, 223 reviews

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

Condo in Orlando

4.84 out of 5 average rating, 128 reviews

SALE! Pool, Lake Views, Disney Fireworks, SALE #5

A newly updated luxurious and spacious condo at Blue Heron Beach Resort for six overlooking beautiful 400+ acre lake Bryan! Guest will have access to first-class amenities available on property which is minutes away from all the Orlando fun and excitement. Gorgeous views from Disney fireworks to true nature along with water sports, several pools, nearby restaurants will complete your experience. Perfect stay for families and people traveling for vacation or work.

Condo in Kissimmee

4.98 out of 5 average rating, 110 reviews

Condo on the top floor with lake view near Disney!

I invite you to stay in this beautiful condominium where you can enjoy splendid views and enjoy the unique sunrises and sunsets of Florida on our balcony or prepare your favorite dish in our luxurious kitchen while your children relax in our Frozen themed room, the children will love it! We also enjoy a privileged location for Orlando’s main attractions, such as Disney, Universal, SeaWorld and Legoland, which is a few miles from our Resort

Vacation rentals for every style

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Popular amenities for Winter Haven waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Rental unit in Kissimmee

4.84 out of 5 average rating, 113 reviews

*LaKe ViEwS* NEW!Condo 3/2 10 min to DiSnEy*

Rental unit in Florida Center

4.9 out of 5 average rating, 144 reviews

18 - Near Universal and International Dr

Rental unit in Florida Center

4.86 out of 5 average rating, 101 reviews

BEST Views~2B2B~Universal~Disney

Rental unit in Kissimmee

4.8 out of 5 average rating, 129 reviews

3 Bd/2 Ba Sleeps 8! Storey Lake (3141-208)

Rental unit in Kissimmee

4.96 out of 5 average rating, 159 reviews

Lovely one bedroom apartment.

Rental unit in Kissimmee

4.96 out of 5 average rating, 136 reviews

WATER View 4BR/Elevator/DISNEY Area

Rental unit in Kissimmee

4.9 out of 5 average rating, 129 reviews

Luxury 2/2 Condo, close to Disney/Free Water Park

Rental unit in Orlando

4.92 out of 5 average rating, 145 reviews

Spacious + Lake View:3b2b w/KingBed,2mi to Disney!

Waterfront house rentals

Home in Davenport

4.89 out of 5 average rating, 110 reviews

Private Waterfront Pool Home - "Lily Pad Landing"

Home in Kissimmee

4.98 out of 5 average rating, 84 reviews

Waterfront 8Br5Ba Game Room/Pool/Spa/Office Space

Home in Lakeland

4.82 out of 5 average rating, 137 reviews

Florida Lake View With Private Pool And Fishing

Home in Kissimmee

4.89 out of 5 average rating, 113 reviews

9 bdrm w/pool |Close to Disney, EV charging

Home in Winter Haven

4.94 out of 5 average rating, 83 reviews

Lakefront Home on the Winter Haven Chain O’Lakes!

Home in Kissimmee

4.72 out of 5 average rating, 104 reviews

Watersedge of Indian Wells Private Pool & Spa

Home in Davenport

4.93 out of 5 average rating, 104 reviews

Beautiful Pool Home With Rear Conservation Views

Home in Kissimmee

4.88 out of 5 average rating, 122 reviews

Sunset Lakes 5 BDR Pool home close to Disney parks

Waterfront condo rentals

Condo in Kissimmee

4.93 out of 5 average rating, 129 reviews

Storey Lake Water Park Resort Condo next to Disney

Condo in Orlando

4.91 out of 5 average rating, 103 reviews

P12#Vista Cay/Lakeview/Newly Renovated/Walk OCCC

Condo in Orlando

4.97 out of 5 average rating, 324 reviews

Luxurious Waterfront Resort near Disney &Universal

Condo in Orlando

4.87 out of 5 average rating, 245 reviews

Spacious 1King/2Bath w/stunning lake view

Condo in Davenport

4.87 out of 5 average rating, 128 reviews

A Resort Getaway with many amenities

Condo in Orlando

4.91 out of 5 average rating, 106 reviews

2-bedroom condo w/ stunning lake and Disney views

Condo in Kissimmee

4.89 out of 5 average rating, 190 reviews

Marvelous apartment near Disney first floor

Condo in Davenport

4.94 out of 5 average rating, 143 reviews

Island Style at Bahama Bay - Minutes to Disney!

Quick stats about waterfront rentals in Winter Haven

Total rentals
80 properties
Nightly prices starting at
G$8,349 GYD before taxes and fees
Total number of reviews
5.1K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
30 properties have a pool

Destinations to explore