Some info is shown in its original language. Translate
Airbnb your place

Pet-friendly holiday rentals in Cypress Gardens

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in Cypress Gardens

  • Total holiday rentals

    Explore 30 holiday rentals in Cypress Gardens

  • Nightly prices starting at

    Cypress Gardens holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Cypress Gardens holiday rentals include Wi-Fi access

  • Popular amenities for guests

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

  • 4.8 Average rating

    Cypress Gardens stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated pet-friendly home rentals in Cypress Gardens

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Superhost
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.
Home in Winter Haven

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

PetsOutdoor spacesAccuracy

4.9 out of 5 average rating, 183 reviews
Guest favourite
Home in Lake Wales

Sunshine on the Lake | Boat Slip+Lakefront Fishing

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

PetsOutdoor spacesValue

4.93 out of 5 average rating, 138 reviews
Top Guest favourite
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.
Home in Winter Haven

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!

Outdoor spacesPetsQuiet

4.98 out of 5 average rating, 138 reviews
Guest favourite
Three thoroughbred horses graze peacefully on a lush green pasture. The area is surrounded by tall trees, providing shade and a natural backdrop. A glimpse of a trailer can be seen in the background, indicating the farm's working environment.
Guest suite in Winter Haven

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. The dock has plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door. Please note there is no barrier around pool and all children (anyone under age of 18)must be supervised at all times. Guests must swim at their own risk. You may see horses in the paddocks. The pool deck overlooks the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

Outdoor spacesWalkabilitySleep quality

4.95 out of 5 average rating, 314 reviews
Guest favourite
An aerial view of a single-story home is presented, showcasing a well-maintained lawn and driveway. The surrounding neighborhood features a mix of greenery and residential structures, contributing to a welcoming suburban atmosphere.
Home in Winter Haven

Extra large home! Bring Your Boat & all the Toys!

Bring your boat, skis, fishin’ pole, or any other water toys! We supply ping pong, corn hole, bicycles and other toys! Directly across from Lake Howard boat ramp and 10 minutes from LegoLand! Enjoy this spacious, well-equipped 2300 sf home that has everything you need to enjoy your stay in Winter Haven, aka Chain of Lakes City, a quaint downtown with free parking-- and just a skip away from Disney and Universal. This getaway is an above-average accommodation both in style and comfort!

WalkabilityOutdoor spacesBackyard

4.95 out of 5 average rating, 101 reviews
Guest favourite
A large outdoor space features a private pool surrounded by loungers in blue and a shaded dining area. A patio table with chairs is placed in the foreground, while a safety fence encloses the pool area, providing a secure environment.
Home in Winter Haven

Kid-friendly Home w/ Pool & BBQ

Enjoy a delightful stay in our Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, washer, Wi-Fi, fully equipped kitchen, baby proofed, and BBQ to make your stay comfortable. Enjoy the private pool, free parking, and large patio. Our house is 20 mins away from LEGOLAND and 50 mins away from Disney Parks and attractions. Discover Winter Haven’s chain of lakes with all the water sports and its surroundings in the best way. We look forward to hosting you!

WalkabilityOutdoor spacesHeating

4.98 out of 5 average rating, 124 reviews
Guest favourite
A serene backyard features a clear swimming pool surrounded by a tiled deck. Sun loungers are positioned around the pool, with a shaded dining area beneath a striped umbrella. Lush greenery and tall trees provide a natural backdrop, enhancing the outdoor space.
Home in Cypress Gardens

Florida Oasis w/ Pool near LEGOLAND

We have added a modern twist to the design of this 1950's home with all the modern appliances and finishes. This home is nestled in-between 2 lakes among the Winter Haven Chain of Lakes! The backyard is a Florida Oasis of a great pool and pool deck with plenty of fun available with games for you and the kids, or just enjoy laying peacefully in the sun! 2.5 mile drive from Legoland 3.5 mile drive from Downtown Winter Haven with great restaurants and small town unique shops.

Outdoor spacesPetsBeach

4.79 out of 5 average rating, 354 reviews
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

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.

PetsOutdoor spacesCondition

4.92 out of 5 average rating, 226 reviews
Top Guest favourite
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.
Home in Winter Haven

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!

Outdoor spacesPetsView

4.98 out of 5 average rating, 125 reviews
Guest favourite
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.
Cottage in Cypress Gardens

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!

Outdoor spacesPetsTV

4.84 out of 5 average rating, 179 reviews
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 Cypress Gardens

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 11 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.

WalkabilityOutdoor spacesBathroom

4.97 out of 5 average rating, 151 reviews
Top Guest favourite
A modern living area features a sectional sofa adorned with blue and white decorative pillows. A round coffee table with a marble top sits on a textured area rug. Natural light fills the space through sheer curtains, complemented by a stylish console table and a round mirror.
Home in Winter Haven

Cozy 3 bedrooms 2 bathrooms

Relax with the whole family at this peaceful and charming home in Winter Haven.This home is centrally located and is within walking distance to Lake Howard , downtown winter haven and plenty attractions We are located 10 minutes from Legoland, Peppa Pig Park, five minutes to Advent Health Fieldhouse, five minutes to Winterhaven Hospital, 45 minutes to Walt Disney World, SeaWorld and Busch Gardens.

PetsOutdoor spacesDecor

4.99 out of 5 average rating, 122 reviews

Popular amenities for Cypress Gardens pet-friendly home rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favourite
Home in Lake Wales

Lake Retreat w/Pool & Hot Tub near Bok tower

WalkabilityOutdoor spacesCleanliness

4.86 out of 5 average rating, 100 reviews
Superhost
A renovated house is framed by mature trees, displaying a fenced front yard that features a paved walkway leading to the entrance. The structure includes a simple facade with large windows, allowing natural light to enter the interior.
Home in Auburndale

three bedroom family house, near legoland

WalkabilityOutdoor spacesLaundry

4.91 out of 5 average rating, 207 reviews
Top Guest favourite
The house exterior displays a blend of white wooden siding and warm wooden accents. Two white, vintage-style chairs are positioned on the porch, leading to a central door with decorative glass. A small set of stairs provides access to the entrance.
Home in Lake Wales

Linda Casita de Lake Wales

WalkabilityPetsComfort

4.98 out of 5 average rating, 209 reviews
Top Guest favourite
A serene lakeside view showcases the tranquil waters of Lake Hollingsworth, surrounded by lush greenery and walking paths. Patterns of vegetation are visible along the shoreline, while distant trees line the horizon, creating a peaceful natural landscape.
Home in Lakeland

Lakeland LakeFront 4BD|3BA FSC SEU Sun&Fun Tigers

Outdoor spacesWalkabilityLocation

4.98 out of 5 average rating, 114 reviews
Top Guest favourite
A modern lakefront home is showcased with a clean, spacious facade. Well-maintained landscaping features palm and leafy plants, complementing the beige exterior. A curved driveway leads to a two-car garage, with panoramic views of the lake apparent beyond the property.
Home in Cypress Gardens

Winter Haven Waterfront Retreat

PetsTVFamily

5.0 out of 5 average rating, 45 reviews
Guest favourite
Home in Cypress Gardens

The Haven House

PetsOutdoor spacesAmenities

4.92 out of 5 average rating, 90 reviews
Guest favourite
A spacious living area is highlighted by a light-toned sectional sofa and a ceiling fan above. To the side, a dining table accommodates multiple guests, while an open kitchen is visible in the background. Natural light enters through large front doors, enhancing the inviting space.
Home in Winter Haven

Cozy 3Bed 2Bath Pet-Friendly Home Near Legoland

Outdoor spacesPetsBackyard

4.81 out of 5 average rating, 42 reviews
Top Guest favourite
The exterior of the house showcases a one-story structure with a light-colored facade. A well-maintained lawn with shrubs frames the entrance, which features a covered porch. A driveway provides parking space for a vehicle, and the sky above is slightly clouded.
Home in Winter Haven

Lovely Home on Lilac Lane - Winter Haven

AccuracyDecorQuiet

4.97 out of 5 average rating, 29 reviews

Pet-friendly home rentals with a pool

Superhost
A wooden barrel sauna is situated in a serene garden space surrounded by bamboo. The sauna features two benches and a wooden door, with soft lighting highlighting its natural texture and the tranquil atmosphere of the area.
Campervan/RV in Lake Wales

Bamboo Bus -Sauna/Pool/Fire pit/Grill

Outdoor spacesPetsDecor

4.82 out of 5 average rating, 158 reviews
Superhost
An inviting outdoor space features a gently curving pool with a built-in hot tub, surrounded by a screened enclosure. Comfortable lounge chairs are arranged nearby, with two patterned hammocks and a dining area visible in the background. Soft evening colors fill the sky above.
Home in Davenport

There is no other place you want to be than here.

WalkabilityOutdoor spacesCondition

4.77 out of 5 average rating, 127 reviews
Top Guest favourite
A single-story home showcases a well-maintained front lawn with lush green grass. The house features a welcoming entrance with a central door, flanked by large windows. A driveway leads to a two-car garage with decorative doors, while a fenced yard adds privacy.
Home in Davenport

Sunny-All-Day Pool Vacation Home

WalkabilityPetsAmenities

4.94 out of 5 average rating, 107 reviews
Guest favourite
A private movie theater features a 150-inch screen displaying a Disney image. Black walls and hardwood flooring create a modern atmosphere. Comfortable reclining seats with cup holders are arranged for a cinematic experience, ensuring a cozy and immersive viewing environment.
Villa in Kissimmee

150 Inch 4K Movie Theater Pool & Spa sleeps 16

PetsWalkabilityAccuracy

4.83 out of 5 average rating, 320 reviews
Top Guest favourite
The image displays the Summerville Resort sign, highlighting its proximity to Disney. A comfortable bedroom is shown, featuring two spacious beds and colorful wall art. An inviting patio area with outdoor seating is visible, alongside a community pool surrounded by lounge chairs and palm trees.
Home in Kissimmee

Comfy Family Villa|5min->Disney!

PetsWalkabilityNearby

4.86 out of 5 average rating, 125 reviews
Top Guest favourite
A circular fire pit area is surrounded by multiple light gray Adirondack chairs on a stone patio. The fire pit is filled with glowing flames, creating a cozy atmosphere against a backdrop of a calm lake at dusk, with soft colors in the sky.
Apartment in Winter Haven

Luxury by Legoland 104

Outdoor spacesPetsCheckout

5.0 out of 5 average rating, 43 reviews
Guest favourite
Home in Cypress Gardens

Costa 5BD Lego Themed Pool Home | Your own Resort

WalkabilityOutdoor spacesBathroom

4.86 out of 5 average rating, 58 reviews
Guest favourite
Home in Winter Haven

Luxury Lake Ruby Lakehouse • Dock • Sleeps 8

PetsOutdoor spacesAccess

4.91 out of 5 average rating, 35 reviews

Private, pet-friendly home rentals

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

The Paradise Hide Away

Outdoor spacesPetsAccess

4.94 out of 5 average rating, 227 reviews
Top Guest favourite
An inviting living area features a comfortable tufted chaise lounge and a cozy recliner. A flat-screen TV is mounted above a classic fireplace, surrounded by soft curtains that frame bright windows. The floor showcases warm wooden tones, contributing to a homely ambiance.
Cottage in Lake Wales

Charming, renovated 1917 Cottage

Outdoor spacesPetsTV

4.98 out of 5 average rating, 170 reviews
Top Guest favourite
A charming white cottage is framed by a well-kept lawn, with a brick chimney visible on one side. Lush green shrubs and trees provide shade around the property, and a pathway leads to the entrance, suggesting easy access to the home.
Cottage in Davenport

Classic Cottage in country setting

WalkabilityOutdoor spacesQuiet

4.99 out of 5 average rating, 135 reviews
Superhost
Home in Winter Haven

! My home is your home near legoland ¡

PetsAmenitiesCheckout

4.84 out of 5 average rating, 37 reviews
Top Guest favourite
Home in Winter Haven

"Chalet" lake house/walking path/fenced yard/dock

PetsWalkabilityFamily

4.95 out of 5 average rating, 20 reviews
Guest favourite
A serene lakeside sunset is captured, displaying a blend of pink and orange hues across the sky. The still water reflects the vibrant colors, while the silhouette of a dock and a palm tree frame the scene, creating a tranquil atmosphere.
Home in Eagle Lake

30 minutes to Disney and Universal Studios

ViewHospitalityAmenities

4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Winter Haven

Cozy 3br 2ba Winter Haven Getaway Chain of Lakes

WalkabilityQuietAir conditioning

5.0 out of 5 average rating, 15 reviews
Top Guest favourite
Guesthouse in Dundee

New Modern Guest House! Great location. Smoke-Free

CheckoutCheck-inFamily

4.98 out of 5 average rating, 45 reviews

When is the best time to visit Cypress Gardens?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$176 AUD$180 AUD$185 AUD$202 AUD$174 AUD$164 AUD$176 AUD$176 AUD$176 AUD$174 AUD$183 AUD$176 AUD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Destinations to explore