Vacation rentals in Cypress Gardens

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Top-rated vacation rentals in Cypress Gardens

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Guest favorite

Guesthouse 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 !

Dec 16 – 23

$64 per night

Superhost

Cottage in Winter Haven

4.8 out of 5 average rating, 117 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!

Jan 1 – 8

$116 per night

Guest favorite

Guesthouse 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

Jun 18 – 25

$110 per night

Guest favorite

Apartment 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

Jun 13 – 20

$74 per night

Superhost

Guesthouse in Winter Haven

4.87 out of 5 average rating, 231 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 ****

Dec 9 – 16

$73 per night

Guest favorite

Guesthouse in Winter Haven

4.84 out of 5 average rating, 144 reviews

Adorable 1 bedroom Guesthouse near Lego Land

This is a beautiful and private place offers a queen size bed, newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! We are located less than 8.6 miles from Legoland & under 6.2 miles from the Lake Myrtle Sports complex. Winter Haven is halfway between Orlando and Tampa. Around 29 miles to Disney World, Universal and Sea World. Around 38 miles to Bush Gardens, Dali museum, Aquarium and much more!

Jun 23 – 30

$75 per night

Guest favorite

Guesthouse 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!

Aug 12 – 19

$118 per night

Guest favorite

Guesthouse 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.

Aug 26 – Sep 2

$84 per night

Guest favorite

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.

Aug 13 – 20

$112 per night

Guest favorite

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

Dec 2 – 9

$88 per night

Guest favorite

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)

Jul 23 – 30

$100 per night

Superhost

Home in Winter Haven

4.87 out of 5 average rating, 109 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.

Nov 20 – 27

$85 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cypress Gardens vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Cypress Gardens's top sights

LEGOLAND Florida Water Park104 locals recommend

Azteca D' Oro8 locals recommend

Cypress Lanes6 locals recommend

Harry's Old Place17 locals recommend

Publix Super Market at Winter Haven Square6 locals recommend

Beef 'O' Brady's6 locals recommend

Other great vacation rentals in Cypress Gardens

Guest favorite

Home in Winter Haven

5.0 out of 5 average rating, 44 reviews

Glass Haven: Serene Getaway 7 min from Legoland!

Feb 28 – Mar 7

$139 per night

Guest favorite

Home in Winter Haven

4.97 out of 5 average rating, 62 reviews

The Dalt Retreat

Jul 24 – 31

$110 per night

Guest favorite

Home in Eagle Lake

4.87 out of 5 average rating, 15 reviews

Quaint Cottage. 6 mi to Legoland. Pet friendly!

Jul 13 – 20

$93 per night

Guest favorite

Home in Winter Haven

4.89 out of 5 average rating, 36 reviews

Newly remodeled House 3BR/2BA

Feb 19 – 26

$91 per night

Guest favorite

Guest suite in Winter Haven

4.86 out of 5 average rating, 73 reviews

Cute & Cozy Guesthouse in Winter Haven

Jun 3 – 10

$70 per night

Guest favorite

Home in Winter Haven

5.0 out of 5 average rating, 10 reviews

Cozy Lakefront Home w/ Pool -7 mins from Legoland

Sep 23 – 30

$132 per night

Guest favorite

Home in Winter Haven

4.99 out of 5 average rating, 93 reviews

Beautiful Lake House Boating Fishing near Legoland

Jun 17 – 24

$103 per night

Guest favorite

Home in Winter Haven

4.98 out of 5 average rating, 42 reviews

The Family Friendly Fun House

Oct 14 – 21

$153 per night

Show all

Quick stats about vacation rentals in Cypress Gardens

Total rentals
90 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
5.3K reviews
Nightly prices starting at
$30 before taxes and fees

Frequently Asked Questions

Do house rentals in Cypress Gardens have a kitchen?
Absolutely! We offer over 50 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 House Rentals in Cypress Gardens?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with free parking, over 60 homes with air conditioning, over 60 homes with wifi, over 50 homes with a kitchen, 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 30 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 60 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 $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Vacation rentals in Cypress Gardens

Top-rated vacation rentals in Cypress Gardens

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Cypress Gardens vacation rentals

Stay near Cypress Gardens's top sights

Other great vacation rentals in Cypress Gardens

Home in Winter Haven

Home in Winter Haven

Home in Eagle Lake

Home in Winter Haven

Guest suite in Winter Haven

Home in Winter Haven

Home in Winter Haven

Home in Winter Haven

Quick stats about vacation rentals in Cypress Gardens

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Cypress Gardens have a kitchen?

Do house rentals in Cypress Gardens have free parking?

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

Do house rentals in Cypress Gardens have air conditioning?

Are there Cypress Gardens vacation rentals on Airbnb with pools?

Are there family-friendly vacation rentals in Cypress Gardens?

Are there pet-friendly vacation rentals in Cypress Gardens?

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

Do house rentals in Cypress Gardens have wifi?

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

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