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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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Cottage in Winter Haven

4.81 out of 5 average rating, 118 reviews

9 Just Beachin' Cabin 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!

Oct 25 – Nov 1

G$27,243 GYD per night

Villa in Lake Wales

4.99 out of 5 average rating, 179 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

Nov 6 – 13

G$31,984 GYD per night

Apartment in Winter Haven

4.99 out of 5 average rating, 137 reviews

STAR WARS Galaxy WORLD near LEGO land/Disney World

In a land far far away here it is Star Wars Galaxy world apartment. 6 months in the making. If you love Star Wars you will be amazed and thrilled. Two balconies included one overlooking lake and one looking over Garys world museum. Play a game of pool .. Full kitchen with washer dryer included. All the modern technology included laptop. Blue tooth. Charging stations and wireless charging. All Star Wars movies,music, Xbox available. 13 minutes from Legoland,45 min. Disney and universal studios

May 4 – 11

G$28,990 GYD per night

Farm stay in Lakeland

4.95 out of 5 average rating, 112 reviews

The Barn at Crews Lake Ranch, near Tampa & Disney

Situated on a 240-acre working ranch with a private lake, this 1-bed, 1-bath modern farmhouse sleeps 4 and offers fishing and nature walks! The 725 sq. ft. cottage-style home includes an open floor plan with full kitchen, washer/dryer and two 250 sq. ft. porches, perfect for coffee or a glass of wine. The home boasts a relaxed, cozy atmosphere in a rustic setting. This private ranch estate will create a memorable stay for your Central Florida getaway. Pets welcome for a small fee!

Feb 15 – 22

G$34,363 GYD per night

Apartment in Auburndale

4.95 out of 5 average rating, 214 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

Jun 3 – 10

G$17,648 GYD per night

Cottage in Eagle Lake

4.99 out of 5 average rating, 223 reviews

Central FL Lake House, Sleeps 5, Close to Legoland

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!

Jan 17 – 24

G$50,885 GYD per night

Guesthouse in Winter Haven

4.87 out of 5 average rating, 232 reviews

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 ****

Aug 14 – 21

G$14,944 GYD per night

Condo in Davenport

4.84 out of 5 average rating, 140 reviews

Full Service Gated Resort, Close to Disney & MCO!

Minutes to Theme Parks, Full-Service Resort, Room for the Whole Family, Pools & More! WKLY & MTHLY DISCOUNTS! This 3-bedroom villa at Bahama Bay Resort & Spa is ideal for family or group vacations. Comfortable queen beds are standard in the main bedroom and first guest bedroom, while the second guest bedroom features two twin beds. The villa features two full bathrooms. All resort amenities are free and available to guests. 24/7 guard gate and front desk service.

Sep 8 – 15

G$24,353 GYD per night

Home in Winter Haven

4.9 out of 5 average rating, 154 reviews

Hidden Haven Lakehouse Pool by Legoland

Relax in style in this 96 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.

Aug 28 – Sep 4

G$39,374 GYD per night

Guest suite in Winter Haven

4.91 out of 5 average rating, 140 reviews

2 Bedroom Winter Haven Guest Suite

Private lock-off unit. Only shared between your party. 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

Sep 26 – Oct 3

G$21,165 GYD per night

Cabin in Davenport

4.92 out of 5 average rating, 170 reviews

$89! Cozy Cabin- Disney 20 Miles Away!

Book with us now and receive access to all of these amenities✨: •Lightning Fast Internet •Covered Patio •Safe Gated Location •Keypad Entry Door •Comfortable Queen Sized Bed •Cable TV (Adjustable) •Modernized Brand New Full Bathroom •Nearby All Major Attractions, Theme Parks, and Malls •Outdoor Dining Area •Kitchen, Fridge/Freezer, & Breakfast Nook •Complimentary Coffee & Breakfast •Cooking Equipment •And Much More! Book with us now!

Jun 6 – 13

G$22,170 GYD per night

Home in Auburndale

4.94 out of 5 average rating, 146 reviews

Lake Whistler Beach House with lakefront pool

The Lake house is a resort with Paddle boards/Kayaks at no cost to our guests. Enjoy the entire yard and non-public lake with a private beach which offers you fishing and water sports (jet skis are additional). The main house has a pool table,air hockey and live darts! Also there is a BBQ, 4 TV's, cable, internet, movie library and washer/dryer, Pool and pool Jacuzzi. Small fenced back yard for pets (pet fee required).

Apr 23 – 30

G$80,347 GYD per night

Vacation rentals for every style

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Unique stays

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Popular amenities for Winter Haven waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Kissimmee

4.95 out of 5 average rating, 134 reviews

Lovely one bedroom apartment.

Sep 21 – 28

G$18,706 GYD per night

Apartment in Kissimmee

4.83 out of 5 average rating, 116 reviews

Spacious Apartment near Disney

Jul 21 – 28

G$27,787 GYD per night

Apartment in Orlando

4.9 out of 5 average rating, 133 reviews

1804-Near Universal and International Dr

Oct 14 – 21

G$30,247 GYD per night

Apartment in Kissimmee

4.98 out of 5 average rating, 146 reviews

Modern Apartment with lake view Close to Disney

Nov 2 – 9

G$43,454 GYD per night

Apartment in Kissimmee

4.99 out of 5 average rating, 146 reviews

2 BR Condo in Resort, just 10 min from Disney_303

Jul 12 – 19

G$47,564 GYD per night

Apartment in Kissimmee

4.93 out of 5 average rating, 121 reviews

BRANDNEW 2BR - LakeView STOREYLAKE - NEARDISNEY

Sep 24 – Oct 1

G$37,274 GYD per night

Apartment in Kissimmee

4.9 out of 5 average rating, 111 reviews

Luxury Apt at Storey Lake, close to Disney World

Sep 10 – 17

G$36,052 GYD per night

Apartment in Kissimmee

4.87 out of 5 average rating, 102 reviews

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

Jul 4 – 11

G$48,762 GYD per night

Waterfront house rentals

Home in Clermont

4.93 out of 5 average rating, 187 reviews

Lake Front Home with private Dock on Lake Louisa

Apr 16 – 23

G$35,850 GYD per night

Home in Lakeland

4.82 out of 5 average rating, 130 reviews

Florida Lake View With Private Pool And Fishing

Aug 28 – Sep 4

G$48,751 GYD per night

Home in Kissimmee

4.84 out of 5 average rating, 205 reviews

3 bedroom Villa in Kissimmee

Jun 28 – Jul 5

G$30,860 GYD per night

Home in Lakeland

4.92 out of 5 average rating, 143 reviews

Family Lake House Get Away With a Pool!

Nov 11 – 18

G$92,578 GYD per night

Home in Winter Haven

4.95 out of 5 average rating, 82 reviews

3/2 House w Heated Pool 5mins to Legoland

Jul 29 – Aug 5

G$37,029 GYD per night

Home in Winter Haven

5.0 out of 5 average rating, 11 reviews

Cozy Lakefront Home w/ Pool -7 mins from Legoland

Dec 13 – 20

G$42,551 GYD per night

Home in Lakeland

4.96 out of 5 average rating, 80 reviews

Cozy Lake House Retreat - Amazing Views !

Nov 7 – 14

G$30,108 GYD per night

Home in Winter Haven

5.0 out of 5 average rating, 16 reviews

Cozy on the Canal near Legoland

Oct 8 – 15

G$45,423 GYD per night

Waterfront condo rentals

Condo in Davenport

4.94 out of 5 average rating, 135 reviews

Island Style at Bahama Bay - Minutes to Disney!

Sep 4 – 11

G$24,191 GYD per night

Condo in Orlando

4.87 out of 5 average rating, 167 reviews

Beautiful Lakeview ★ 1 Mile to Disney ★ 1BDR/2BA

May 21 – 28

G$21,741 GYD per night

Condo in Kissimmee

4.94 out of 5 average rating, 109 reviews

Cheery 2BR Condo w/zero entry pool near Disney

Oct 11 – 18

G$20,086 GYD per night

Condo in Orlando

4.89 out of 5 average rating, 327 reviews

FantasticView, 1 BR/2BA, 1 MILE TO DISNEY-Sleeps 6

Nov 9 – 16

G$28,513 GYD per night

Condo in Kissimmee

4.98 out of 5 average rating, 289 reviews

Gorgeous❤️ Pool & Lake View Condo near Disney Parks

Aug 30 – Sep 6

G$26,968 GYD per night

Condo in Kissimmee

4.96 out of 5 average rating, 154 reviews

Welcome to our Son Shine condo ....

Mar 25 – Apr 1

G$28,927 GYD per night

Condo in Orlando

4.88 out of 5 average rating, 109 reviews

UPSCALE townhouse minutes to all attractions

Jun 24 – Jul 1

G$23,570 GYD per night

Condo in Orlando

4.97 out of 5 average rating, 296 reviews

Luxurious Waterfront Resort near Disney &Universal

Sep 24 – Oct 1

G$36,195 GYD per night

Quick stats about waterfront rentals in Winter Haven

Total rentals
70 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
4.8K reviews
Nightly prices starting at
G$8,363 GYD before taxes and fees

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