Holiday houses in Cypress Gardens

5 out of 5 average rating, 38 reviews

An aerial view showcases a spacious yard bordering a peaceful canal, leading to a large lake. The well-maintained property features lush greenery and a swimming pool, inviting relaxation. The surrounding homes reflect a tranquil community atmosphere, enhancing the serene waterfront setting.

Home in Auburndale

Little Castle on the canal on lake Arietta

Serenity and Beauty in the wonderful canal front house sitting on nearly 1 acre lot hidden in a secluded cul-de-sac. Enjoy the pool, volleyball on the yard, kayaking, paddle board on the canal that leads to a big lake. Well landscaped yard. Enter the front door, you'll greeted by high vaulted ceiling great room. Total 2300 sqft with 3 bedrooms and 2 full bath. Two indoor dining areas. Open floor one story layout, with wood and tile floor throughout, there is no carpet. Immaculately clean.

Home in Downtown Winter Haven

A well-lit living room features a comfortable gray sofa and a light pink chair. A round coffee table is centered on a soft rug, while a contemporary TV stand holds a flat-screen television. Large windows provide natural light, and a door leads outside.

4.9 out of 5 average rating, 161 reviews

3/2 Great Family Home Near Legoland

Enjoy easy access to Legoland (4 mi) & charming Downtown (1 mi) from this centrally-located home. Designed to make you feel right at home during your family getaway, the whole home is private to you. We are pet friendly! Featuring a kitchen ready to make a home meal, a fully fenced private back yard, keyless entry, & free, ample parking for multiple cars and a trailer. Street parking is also allowed. Locally owned & operated. We are excited to share our city and provide exceptional service

4.97 out of 5 average rating, 108 reviews

Adult-Only Getaway w/ Mermaid Pool | 18+, Private

🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

The outdoor pool area features a heated saltwater swimming pool with colorful floats, including a swan and a duck. The patio is paved with light-colored tiles and is surrounded by comfortable seating and decorative lighting, reflecting a welcoming space for relaxation and fun.

5 out of 5 average rating, 76 reviews

Waterfront Heated Pool Putting Green Dock Legoland

Sunset Haven is a luxurious, contemporary 3,581-square-foot lakefront retreat set on nearly one acre along the shores of beautiful Lake Summit, part of Winter Haven’s famous Chain of Lakes. From the moment you step inside, your eye is drawn through the home to sweeping lake views beyond the pool deck, where breathtaking sunsets can be enjoyed almost every evening. Thoughtfully designed, this exceptional residence offers an impressive array of amenities for a truly unforgettable stay.

An aerial view captures the expansive backyard featuring a large, fenced saltwater pool surrounded by a sunbathing area. The well-maintained lawn leads to the upgraded lakefront home, showcasing its brick exterior and covered patio, with trees and neighboring properties visible in the background.

4.98 out of 5 average rating, 99 reviews

Family Friendly Lake House W/ Pool Near Legoland

At this spacious, upgraded lakefront home, with a sandy beach and private dock, spend your days fishing, floating, and boating through the lake. Back at the house, the brand-new saltwater pool has a sun shelf, color-changing lights, and jets the kids will love! Relax on the expansive covered patio while you grill and grab drinks from the mini-fridge, or take a break to enjoy the 900 sqft game room with a pool table, foosball, basketball, darts, and arcade games. 10 min from Legoland!

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, 109 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. This is a mother-in-law suite that is connected to the main home. 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. Dog welcome with prior approval and pet fee. Boat parking at dock. Boat rental available at Central Florida Water Sports. Private entry with keyless touchpad.

Superhost

4.75 out of 5 average rating, 48 reviews

Casa Inman – 3BR Luxury Stay Minutes from Legoland

Welcome to Casa Inman, your elegant Winter Haven retreat just minutes from LEGOLAND Florida. This modern 4-bedroom, 2-bath home with a private office offers comfort, space, and style for up to 10 guests. Enjoy the open-concept living area, fully equipped kitchen, and private patio. Located near Lake Hamilton, golf courses, and downtown restaurants, Casa Inman combines convenience and tranquility. Our team provides attentive service to make your stay exceptional.

Guesthouse in Winter Haven

A wooden dock extends over the calm waters of Lake Howard, bordered by lush grass on either side. A sign indicating 'Private Property' stands at the dock's entrance, while the clear blue sky is dotted with fluffy white clouds in the background.

5 out of 5 average rating, 97 reviews

Charming Lakeside Cottage

Escape to our cozy lakeside cottage, featuring a dock that’s perfect for watching sunrises, fishing, and launching your kayak. The property is on Lake Howard, which is part of the Winter Haven Chain of Lakes. Inside, you’ll find a fully equipped kitchen and comfortable living space for unwinding. Located just a short drive from the excitement of Legoland and Disney World, you can easily explore the area’s attractions while having a peaceful haven to return to.

4.94 out of 5 average rating, 18 reviews

A serene waterfront view captures a vibrant sunset reflected on the lake's surface. Silhouetted palm fronds frame the scene, while a wooden dock extends into the water, creating a peaceful atmosphere for relaxation and contemplation.

Home in Eagle Lake

30 minutes to Disney and Universal Studios

Conveniently located between Orlando and Tampa Bay, Vanderlake provides the perfect getaway for a relaxing weekend with the family. Egrets, sand cranes and ducks make their way through our yard everyday, so enjoy the view of wildlife and aquatic life that love to swim by. A spacious kitchen, paddle boards, an outdoor lanai with a grill and an open concept living space is calling your name! Come stay a while and relax with us! We would love to have you!

4.92 out of 5 average rating, 63 reviews

A cozy living area is presented, featuring a dark sectional sofa complemented by a throw blanket and decorative pillows. Two round coffee tables with wooden tops provide additional surface space. Soft gray tiles cover the floor, while light-filtering window treatments adorn the windows.

Home in Lake Wales

Lake Wales House by DVH.

Visit Lake wales and stay with us. 🎃LEGOLAND 🎃BOK TOWER GARDENS 🎃JumpFlorida skydiving 🎃Central Florida Adventure Park - Authentic Dude 🎃Ranch Experience 🎃LAKE KISSIMMEE STATE PARK 🎃ALLIGATOR COVE TOURS 🎃Lake Wales Country Club 🎃FLORIDA'S NATURAL GROWERS GROVE HOUSE 🎃Bella Cosa 🎃Sugar Barn 🎃TMC GUIDE SERVICE 🎃Auburndale Motor Speedway 🎃Wallaby Ranch 🎃Lake Wales bowling 🎃Port 27 Live your best vacaction in Lake Wales Florida.

Cottage in Cypress Gardens

The entrance features wooden steps leading up to a covered porch, flanked by tropical foliage. Two chairs are positioned on the porch, offering a place to relax. The home’s exterior is painted in soft green, complemented by light-colored trim.

4.84 out of 5 average rating, 158 reviews

5 - Life's a Beach Retreat 1bed/1bath - Unit 13

The 1-bedroom, 1-bathroom home features a fully equipped kitchen and covered front porch, making it the perfect spot to reel in a relaxing getaway. A cozy one-bedroom unit on the property of Cypress Inlet. Less than 10 minutes from LegoLand and Peppa Pig theme park. The property is on a canal that leads to Lake Eloise and the WH Chain of Lakes, and has boat ramp access and docks available; this vacation rental is an angler's paradise!

A spacious living area is presented with a sectional sofa, a wooden coffee table, and a wall-mounted television. Large windows allow natural light and views of the outdoor patio. The room features light-colored walls and art pieces that add a modern touch.

4.95 out of 5 average rating, 152 reviews

Legoland Getaway 7 mins • Sleeps 7 • Elevator

Come relax with your family in this peaceful 2BR/2.5BA home, just 7 minutes from LEGOLAND®. Sleeps up to 7 guests, with pool access, board games, and arcade fun for all ages! Wheelchair accessible with elevator between floors. No parties, no smoking. Primary guest must be 25+ and present during stay; ID may be required.

Popular amenities for Cypress Gardens holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Cypress Gardens

4.93 out of 5 average rating, 30 reviews

The saltwater heated pool is enclosed within a screen patio, surrounded by a well-maintained white fence. Comfortable cushioned seating is visible nearby, along with potted plants adding a touch of greenery. Clear blue skies enhance the peaceful atmosphere of the outdoor space.

Home in Highland City

Relax in Heated Saltwater Pool w/ Screened Lanai

5 out of 5 average rating, 12 reviews

Cottage in Auburndale

Lakefront Boho Cottage w/ Fire Pit | Still Waters

The two-story lakehouse features light-colored exterior walls with blue shutters and a welcoming front door. Lush greenery surrounds the entrance, complemented by flower beds. The driveway leads to a spacious front yard, creating an inviting atmosphere in a tranquil neighborhood.

4.93 out of 5 average rating, 27 reviews

1937 family lakehouse kids and pet friendly

4.93 out of 5 average rating, 44 reviews

An enclosed swimming pool area is surrounded by a spacious screen enclosure, providing a clear view of lush greenery and a privacy fence in the background. Sunlight streams in, creating a bright and inviting atmosphere, while potted plants add touches of color around the pool's edge.

Home in Auburndale

Florida Oasis

A serene view of a private pool, framed by a screened enclosure, reflects the warm glow of the sunset. The water glistens under the soft light, with lush palm trees providing a tropical backdrop. The expansive lake is visible beyond the pool area.

5 out of 5 average rating, 30 reviews

Private Pool, Beach & Dock on the Chain of Lakes

4.95 out of 5 average rating, 21 reviews

An inviting pool area is surrounded by a screened enclosure, featuring a clear blue pool with gentle water features. Lush palm trees and vibrant foliage create a serene atmosphere. Comfortable lounge chairs are positioned nearby, offering a perfect spot for relaxation.

Home in Lakeland

Lakeland Retreat (Beaches, golf, Disney, Legoland)

5 out of 5 average rating, 143 reviews

A view of the property entrance reveals a wooden deck leading to a separate entrance. Lush green grass and trees surround the area, creating a serene outdoor setting. A neighboring screened porch is visible in the background, enhancing the tranquil atmosphere of the location.

Home in Lake Alfred

LA Loft, Upstairs private studio

A spacious living area features a comfortable sofa facing a dining table for four. Two bedrooms showcase cozy bedding, including a striped patterned bed and a floral patterned duvet cover. Light blue walls create a fresh atmosphere, complemented by ceiling fans and large windows.