Holiday rentals 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

Guest house in Winter Haven

4.95 out of 5 average rating, 202 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 !

27 Dec – 3 Jan

£83 per night

Guest favourite

Guest house in Cypress Gardens

4.83 out of 5 average rating, 12 reviews

2 Bdrm near Legoland guesthouse

Relax at this peaceful place to stay. 2 bedroom 1 bath with fully equipped kitchen with dining for 5. Living room with fiber optics internet - smart TV, charging devices. Private child safety fenced outside - picnic table, grill. Max 4 adults Gated property with a parking in front of the left garage door. Maximum 2 cars .8 miles from Legoland & 30 miles from Disney. Many local eating places within blocks & many national chains within a couple miles. 1 Outside camera of the 3152 front door

9–16 Sept

£115 per night

Guest favourite

Flat in Auburndale

4.96 out of 5 average rating, 212 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

13–20 Oct

£79 per night

Guest favourite

Guest house in Lake Hamilton

4.9 out of 5 average rating, 140 reviews

Luxury Cottage Near Legoland & Chain of Lakes

The Old Florida Cottage, in the quaint community of Lake Hamilton, just 5-miles from Legoland, less than an hour from Disney, and minutes away from the only public boat access to Lake Hamilton, is your perfect getaway! Enjoy a fully-equipped kitchen, a luxurious suite and modern bathroom, surrounded by Old Florida decor. We look forward to welcoming you to the cottage, with its own entrance and dedicated parking, located on a quiet street. Your home away from home!

21–28 Sept

£132 per night

Guest favourite

Guest house in Winter Haven

4.91 out of 5 average rating, 54 reviews

Comfy Guest House

Welcome to our inviting and family-friendly guest house, designed with your comfort and privacy in mind. Ideal for travellers visiting our wonderful city, our 1-bedroom retreat features a cozy queen bed and a full bathroom, ensuring a relaxing stay for up to 2 guest. The well-equipped kitchen area boasts a sink, refrigarator, microwave, cooking appliances, utensils, and a convenient pantry to store your items. Stay connected with our strong WiFi connection.

23–30 Jul

£93 per night

Guest favourite

Home in Winter Haven

4.94 out of 5 average rating, 141 reviews

Cozy Family Home Near Legoland

Relax with the fam after a fun day at LEGOLAND (4.1 miles) or Disney World (36 miles) in our cozy home complete with a well-stocked kitchen, fully-fenced backyard, and comfortable beds. Spend a day on the famous Chain of Lakes (24 canal-connected lakes), catch a free ski show on Lake Silver, wander downtown to shop, or toast a pint at Union Taproom. Winter Haven is centrally located between Tampa and Orlando with plenty of fun nearby for the whole family.

11–18 Nov

£133 per night

Guest favourite

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

21–28 Jul

£96 per night

Superhost

Cottage in Winter Haven

4.84 out of 5 average rating, 119 reviews

5 Ships Ahoy Bungalow Unit 17

Florida’s lakes and biggest attractions are calling you and your family to stay at this vacation rental in Winter Haven! From Legoland and Disney World to the famous Chain of Lakes and golf courses galore, this charming home in Cypress Inlet is minutes from it all. Take your boat out on Lake Eloise, through a private canal right outside the home, or take the kiddos to SeaWorld, a short drive away, before returning to this 2-bedroom 2-bath home.

15–22 Mar

£118 per night

Guest favourite

Guest suite in Winter Haven

4.86 out of 5 average rating, 73 reviews

Cute & Cozy Guesthouse in Winter Haven

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)

3–10 Mar

£79 per night

Guest favourite

Guest house in Auburndale

4.97 out of 5 average rating, 192 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. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

23–30 Jun

£81 per night

Guest favourite

Guest suite in Winter Haven

4.96 out of 5 average rating, 256 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. Fishing available on site. New dock just finished with plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door, horse paddocks and patio overlooking the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

26 Nov – 3 Dec

£103 per night

Superhost

Home in Winter Haven

4.86 out of 5 average rating, 110 reviews

The Flamingo

The Flamingo has been completely refreshed with paint, flooring, beds, furniture and many kitchen amenities. It is located 5 miles from Legoland, 30 miles to Disney World, near great restaurants, lakes, downtown Winter Haven and various shopping and attractions.

4–11 Mar

£98 per night