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Holiday houses in Cypress Gardens

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Top-rated holiday rentals in Cypress Gardens

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A private backyard area is surrounded by lush greenery and tropical plants. A stone patio features a dining set with a canopy overhead. Soft seating is placed nearby, inviting relaxation in a tranquil setting.
Guesthouse in Winter Haven
4.94 out of 5 average rating, 223 reviews

The Paradise Hide Away

This is a beautiful and private place newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! Talk to me if you need different check in/out times? Dogs are allowed with permission. There is a $200 fully refundable pet security deposit to cover any damages that may occur since Airbnb doesn’t cover damages caused by pets plus a non refundable pet fee of $50 per pet for every 1-7 day period and must be paid before checking in !

Top Guest favourite
A balcony view overlooks a serene lake, framed by lush palm trees and vibrant green foliage. Bright blue skies and scattered clouds add to the tranquil setting, while glimpses of the driveway and nearby structures can be seen in the distance.
Apartment in Winter Haven
4.98 out of 5 average rating, 162 reviews

Florida Penthouse in luxurious mansion!

Stay in your own themed Florida apartment . Tropical, palm trees, beaches ,marine life, flamingos throughout this stunning apartment in a multimillion dollar home. After parking on gated driveway walk up to your own private entrance way to paradise. Keyless entrance. One flight up and your viewing gorgeous lake views second to none. Executive kitchen with everything you need to cook a 5 course meal. Outdoor balcony that will leave you amazed. Opulence, security, with Florida Style awaits you!

Top Guest favourite
Home in Winter Haven
5 out of 5 average rating, 21 reviews

Cozy one bedroom home in Winter Haven

Unwind in Winter Haven at this delightful cozy and peaceful home that is centrally located . The space features one bedroom, King size bed ,full bathroom with all the amenities you need. Home Is two minutes to downtown Winter Haven, Walking distance to Lake Howard, five minutes to Winter-Haven Hospital, and advent health Fieldhouse , 10 minutes to Legoland and peppa pig park.We are forty-five minutes to Disney World, Universal Studios, adventure, Island, and Busch Gardens.

Top Guest favourite
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.
Home in Winter Haven
4.95 out of 5 average rating, 103 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.

Top Guest favourite
Guesthouse in South Lake Morton Historic District
4.89 out of 5 average rating, 129 reviews

Studio apt in Historic area of Lakeland

This second story studio is on our homes property. It has a Queen bed, bathroom and kitchen. It is nestled in the historic area of Lakeland, one block in from The "Frank Lloyd Wright" designed Florida Southern college, tours are available! Our Cobblestone streets take you to our neighborhood restaurants, the art museum, library, Hollis garden, we are between two lakes-Hollingsworth it has a great walking/running path, and Lake Morton a bird paradise. All within walking distance.

Top Guest favourite
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.
Apartment in Auburndale
4.96 out of 5 average rating, 248 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

Top Guest favourite
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
4.99 out of 5 average rating, 287 reviews

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!

Top Guest favourite
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.
Home in Winter Haven
4.91 out of 5 average rating, 199 reviews

Legoland Lakehouse Canoe & Kayak 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.

Top Guest favourite
A serene pool area is enclosed by a protective screen, featuring a clear swimming pool surrounded by a tiled patio. A comfortable seating area is visible in the background, with a stylish egg chair. Lush greenery enhances the tranquil setting.
Guesthouse in Auburndale
4.97 out of 5 average rating, 245 reviews

Private Poolside Villa

Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. The apartment is behind my personal home with no connecting doors. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Top Guest favourite
A comfortable living space features a large sectional couch adorned with decorative pillows. A mirror and wall art enhance the ambiance. Natural light enters through the front door, and a dining table is situated nearby. A ceiling fan provides a refreshing atmosphere.
Guest suite in Winter Haven
4.89 out of 5 average rating, 110 reviews

Cute & Cozy in Winter Haven, Florida

The guesthouse Cute & Cozy is private yet adjacent to the main house (owner lives) and has its own entrance. Located in central Florida, between Orlando and Tampa; 3 miles from Legoland, 5-10 minute walk from shopping and restaurants on Cypress Gardens Blvd. The Cute & Cozy is also in a great location from Florida's amazing beaches, just under 2 hours east or west. Maybe an hour drive to Disney, SeaWorld and Universal (depends traffic)

Top Guest favourite
A private backyard features a clean in-ground pool surrounded by a paved patio. Two lounge chairs are positioned beside the pool, and a dining set with four chairs sits nearby. Lush greenery and a white privacy fence enhance the serene outdoor setting.
Home in Winter Haven
4.98 out of 5 average rating, 126 reviews

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 10 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.

Guest favourite
The exterior of the tiny house is showcased, featuring a welcoming front porch with steps leading up. Landscaping includes vibrant tropical plants and a stone pathway. The structure is set against a clear blue sky, highlighting the charming design and inviting ambiance.
Tiny home in Winter Haven
4.89 out of 5 average rating, 146 reviews

4 a Tiny House w/ Bunk Bed in Quiet Marina Unit 14

Our cozy tiny house is perfect for when less is more :-). An intimate space for a long reflective weekend or a more affordable option for a few days with the kids at nearby Legoland. Offering a queen-size Murphy bed and two additional single-size bunk beds, the Cypress Inlet Tiny House can comfortably accommodate up to four people. Equipped with a mini-fridge, a microwave, and a Keurig duo (drip & pod) coffee maker.

Popular amenities for Cypress Gardens holiday rentals

When is the best time to visit Cypress Gardens?

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Frequently Asked Questions

  • Do house rentals in Cypress Gardens have a kitchen?

    Absolutely! We offer over 60 house rentals with a kitchen in Cypress Gardens. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cypress Gardens have free parking?

    Absolutely! We offer over 60 house rentals with free parking in Cypress Gardens. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Hotel Rentals in Cypress Gardens?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Cypress Gardens have air conditioning?

    Absolutely! We offer over 60 house rentals with air conditioning in Cypress Gardens. Enjoy a tailored experience with all the comforts you desire.

  • Are there Cypress Gardens vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Cypress Gardens, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Cypress Gardens?

    Cypress Gardens has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Cypress Gardens?

    Four-legged friends are welcome in Cypress Gardens. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Cypress Gardens?

    Yes! Work meets play with ease at over 60 vacation rentals in Cypress Gardens featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Cypress Gardens have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Cypress Gardens. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Cypress Gardens?

    Experience the best of Cypress Gardens with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about holiday rentals in Cypress Gardens

  • Total holiday rentals

    Explore 120 holiday rentals in Cypress Gardens

  • Nightly prices starting at

    Cypress Gardens holiday rentals start at $29 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Cypress Gardens holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Cypress Gardens rentals

  • 4.7 Average rating

    Cypress Gardens stays receive an average rating of 4.7 out of 5 from guests

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