Waterfront holiday rentals in Cypress Gardens

4.98 out of 5 average rating, 199 reviews

The living area features a modern sectional sofa with colorful throw pillows in vibrant red and yellow. A matching ottoman sits in front, accompanied by stylish side tables with lamps. Bright blue walls create a lively backdrop, enhanced by a large abstract painting and adjacent dining space.

Villa in Lake Wales

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

Guest suite in Winter Haven

A comfortable bedroom features a spacious queen bed with decorative pillows and a textured blanket. A cozy seating area is positioned at the foot of the bed. A wooden barn door partially covers a window, while a TV is mounted on the wall above a stylish console table adorned with greenery.

4.9 out of 5 average rating, 200 reviews

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

The exterior of a spacious home is presented, featuring a blue façade and a welcoming entrance. Lush tropical foliage surrounds the property, which is highlighted by palm trees and manicured lawns. A vibrant sunset casts colorful hues in the sky, enhancing the serene atmosphere.

4.98 out of 5 average rating, 127 reviews

Spectacular Waterfront Home in Winter Haven

Enjoy a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. Featuring a chef's kitchen, 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest. We are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary!

Flat in South Lake Morton Historic District

A bright workspace is showcased with large windows offering views of the lake. Two yellow armchairs sit beside a glass-top table. A desk with a lamp is positioned against the wall, with a potted plant adding a touch of greenery.

5 out of 5 average rating, 100 reviews

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!

A serene lakeside view is observed, featuring gently swaying palm trees on the left and a wooden dock extending into the water. A boat is anchored at the dock, surrounded by lush greenery and a clear blue sky.

4.95 out of 5 average rating, 101 reviews

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.

A spacious living area features a striking mural of a serene lake scene, complemented by a cozy seating arrangement. Tropical-themed decor and unique ceiling fixtures add to the ambiance. Natural light filters in, highlighting the stone floor and creating a welcoming environment.

4.99 out of 5 average rating, 141 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 , 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.

4.95 out of 5 average rating, 243 reviews

A wooden deck overlooks the calm waters of Lake Ariana, framed by greenery. A small table with two chairs is positioned to enjoy the view, while a potted plant adds a touch of nature to the space. Spanish moss drapes gracefully from nearby branches.

Flat in Auburndale

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

4.99 out of 5 average rating, 281 reviews

A view of the blue lake house is presented with a well-manicured lawn leading up to it. The house is framed by mature trees, providing shade. A wooden walkway extends toward the entrance, while the serene lake is visible in the background.

Cottage in Eagle Lake

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!

Guest house in Winter Haven

A serene lakefront scene captures a sparkling pool surrounded by palm trees at sunset. The sky features vibrant hues of orange and purple, reflecting in the calm water. Two lounge chairs are positioned beside the pool, creating a peaceful retreat.

4.87 out of 5 average rating, 278 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 ****

An inviting swimming pool is surrounded by a spacious patio area, featuring lounge chairs and a shaded table with an umbrella. The serene view of Little Lake Otis and lush greenery is visible in the background under a partly cloudy sky.

4.92 out of 5 average rating, 191 reviews

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.

A charming lake home is showcased with a light-coloured façade and blue shutters. A welcoming entrance is flanked by decorative chairs, with well-maintained landscaping featuring green grass and flower beds enhancing the outdoor appeal.

4.97 out of 5 average rating, 105 reviews

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!

4.98 out of 5 average rating, 254 reviews

The quaint lakefront cottage is framed by large, leafy trees and draped with Spanish moss. A gravel entrance leads to a welcoming porch, featuring large screened windows. Lush greenery surrounds the property, creating a natural, serene setting.

Guest house in Lakeland

Modern lakeside retreat by SEU and FSC

This 1920’s 1 bedroom 1 bath lakefront historic cottage is separate from the main house with its own entrance, parking, front porch & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks, pedal boat, and fishing poles and tackle are provided for your enjoyment. Come unwind and enjoy the lake views from the hammock and private beach!

Popular amenities for waterfront rentals in Cypress Gardens

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

Aerial view of a resort-style pool area, featuring winding lazy river and colorful waterslides. Surrounding palm trees and lounge chairs enhance the tropical ambiance. The nearby lake provides a scenic backdrop, while various guests can be seen enjoying the water attractions.

4.79 out of 5 average rating, 100 reviews

Magical Holiday+Relax+FreeParking

A well-lit bedroom features a spacious bed with a white quilted cover and decorative pillows. A round mirror is mounted above a side table, complemented by wall art. The room is connected to another area visible through an open door.

4.93 out of 5 average rating, 216 reviews

Lovely one bedroom apartment.

4.88 out of 5 average rating, 164 reviews

A spacious bed with a burgundy coverlet is positioned beneath vibrant yellow walls. Accents include cushions in a mix of patterns. Soft nightstands with warm lamps flank the bed, while colorful artwork adorns the walls, adding character to the inviting space.

Flat in Orlando

Renovated Studio-Near INT'L Drive and Parks!

A large resort-style pool, shaped like a Mickey Mouse head, is surrounded by palm trees and lounge chairs. Guests are seen relaxing on sun loungers and enjoying the water, with umbrellas providing shade in certain areas. Additional smaller pools are visible nearby.

4.91 out of 5 average rating, 129 reviews

Amazing Apartment in Orlando - Kissimmee

The modern kitchen is equipped with stainless steel appliances, including a large refrigerator, microwave, and oven. A granite countertop offers ample workspace, complemented by sleek cabinets. Pendant lights hang above the island, and a dining area is visible in the background.

4.93 out of 5 average rating, 111 reviews

Serenity Lake: Spacious & comfy 3BR/2BA Apartment

The living area features a blue sectional sofa and a round coffee table centered on a patterned rug. A large television is positioned against a feature wall adorned with tropical-themed wallpaper. Bright curtains frame the sliding door, which leads to a balcony with a view.

4.85 out of 5 average rating, 91 reviews

Your Gateway to Adventure and Relaxation

4.96 out of 5 average rating, 111 reviews

Premium LakeView/MoanaRoom/Walk to StoreyClubHouse

A spacious balcony is equipped with woven seating and a glass-top table. Views of a tranquil waterway and lush greenery are visible, framed by modern railings. Soft clouds drift across the sky, enhancing the overall serene atmosphere of the outdoor space.

4.79 out of 5 average rating, 120 reviews

★BRAND NEW APT with LAKEVIEW - Close to Disney★

Waterfront house rentals

4.94 out of 5 average rating, 161 reviews

A spacious lawn is framed by large oak trees draped with Spanish moss. Comfortable lounge chairs are positioned facing the tranquil water, creating a serene outdoor space. The lake is visible in the background, enhancing the natural beauty of the setting.

Home in Auburndale

Lake Whistler Beach House with lakefront pool

4.98 out of 5 average rating, 106 reviews

A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.

Home in Kissimmee

Mickey's Lakefront Villa at Sunset Lakes

A cozy loft bedroom features a spacious bed with soft linens and decorative pillows. A Roku screen projector casts images onto the slanted ceiling. Light from recessed fixtures brightens the room, while minimalist decor includes two small plants and a white dresser against the wall.

4.96 out of 5 average rating, 45 reviews

Lake House by Legoland + Loft & Private Dock

4.8 out of 5 average rating, 114 reviews

A dining area features a wooden table surrounded by beige chairs and a bench. Two decorative blue vases are placed at the center. A stone fireplace serves as a backdrop, with a modern light fixture above. A mirror reflects the room's light blue walls.

Home in Lakeland

Spacious 3BR Home | Peaceful Stay Near I-4

A fire pit is centrally positioned on a stone surface, with flames dancing above decorative stones. Beyond the screen enclosure, lounge chairs are placed near a private pool, surrounded by lush greenery and a thatched-roof palapa, creating a relaxing outdoor setting.

4.92 out of 5 average rating, 39 reviews

Cozy Lakefront Home w/ Pool -7 mins from Legoland

4.99 out of 5 average rating, 149 reviews

An expansive outdoor pool deck is featured, surrounded by lounge seating and shaded areas. A giant outdoor chess set stands nearby, along with a view of the scenic forest and pond. A brightly decorated game area showcases themed decor and entertainment options.

Home in Four Corners

*Luxurious Paradise Mansion: Pool, Spa & Cinema

4.88 out of 5 average rating, 206 reviews

A cozy living area is highlighted by a decorative wall, a TV mounted above a light-colored cabinet, and a plush seating arrangement. A fire pit with glowing embers is visible, providing a warm ambiance. A game table with two chairs and a pool table is present, alongside a screened pool area showcasing a sunset view.

Home in Kissimmee

Waterfront retreat,KING Bed,Heated Pool & Fire Pit

4.99 out of 5 average rating, 148 reviews

A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.

Home in Kissimmee

Heated Pool 15 Minutes to Disney PS5 l Switch

Waterfront apartment rentals

An aerial view of the clubhouse area is displayed, featuring a large pool surrounded by lounge chairs. Palm trees provide greenery around the poolside, while guests can be seen enjoying the water. The architecture of the clubhouse complements the inviting outdoor space.

4.93 out of 5 average rating, 123 reviews

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

4.97 out of 5 average rating, 196 reviews

A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.

Apartment in Kissimmee

303_To Infinity & the Ocean Breeze Apartment

A balcony view showcases a round table and two chairs facing the expansive lake. The serene water reflects the clear blue sky, while the railing provides safety and openness to the picturesque landscape.

4.98 out of 5 average rating, 111 reviews

Disney Area Updated Lakefront Resort Condo 2 BATHS

A spacious living area features a comfortable sectional sofa facing a modern coffee table. Bar stool seating surrounds the kitchen island, with stainless steel appliances visible in the background. Soft lighting and a nautical-themed artwork enhance the room's welcoming ambiance.

4.87 out of 5 average rating, 281 reviews

Spacious 1King/2Bath w/stunning lake view

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

4.97 out of 5 average rating, 402 reviews

Waterfront Resort Condo near Disney and Universal

A bright living area features a cozy gray sofa paired with two stylish yellow chairs. A wooden coffee table sits atop a textured area rug, while large glass doors lead to a balcony that offers views of Lake Bryan.

4.95 out of 5 average rating, 110 reviews

Modern Lake view Condo 1 mile from Disney

4.91 out of 5 average rating, 150 reviews

A modern living room features a light-toned sofa facing a wall-mounted television displaying tranquil landscape imagery. Soft blue LED lighting enhances the space, while a stylish area rug with geometric patterns adds texture. A glimpse of the kitchen can be seen in the background.

Apartment in Kissimmee

Chic Disney Resort Condo • Pool Access Near Parks

The living area features a spacious gray sectional sofa and a wooden coffee table atop a round, textured rug. A large TV is mounted on a media console, and natural light flows through the floor-to-ceiling sliding doors leading to a balcony with lake views.