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Family-friendly vacation rentals in Cypress Gardens

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cypress Gardens

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

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Home in Winter Haven

4.89 out of 5 average rating, 261 reviews

The Old Haven - An Enduring Piece of Nostalgia

This charming home was built in 1908 and is located 45 minutes from Tampa/Orlando. Fully furnished, this space is perfect for families and friends providing plenty of space to sleep 8 people comfortably. With games, puzzles and Dvds, backyard fun for kids while the parents watch from the porch. Enjoy downtown entertainment within walking distance! Home is centrally located to dining, shopping, and small town fare. 4 bar restaurants walking distance on the lake. Live music from Lake sometimes.

Oct 29 – Nov 5

R2,784 ZAR per night

Home in Haines City

4.95 out of 5 average rating, 139 reviews

Luxury Home 4/3 near Disney, 2 Masters

Luxury 4 bedroom home located in a quiet, gated community about 15 miles from Disney World. The travel time to Disney will depend on the traffic but is usually between 30 and 40 minutes. Fully furnished with 2 master King bed suites, one queen bedroom and one bedroom with 2 twin beds. 3 full baths. 5 high definition televisions, high speed Wifi, free long distance phone calls to US, Canada and UK. Large pool and spa. Large game room with many games and activities for children of all ages.

Nov 4 – 11

R3,133 ZAR per night

Guest suite in Kissimmee

4.83 out of 5 average rating, 513 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Hello travelers, we offer a portion of our home with a private entrance off the pool area. Your area has 2 bedrooms with queen beds and internet TVs and a private bathroom. The mini kitchen has a small refrigerator, a coffee maker, microwave and a bread toaster. Please note the pool is shared with my family and another set of travelers. We are happy to continue offering our apartment with a 5-star cleanliness rating. We offer our home to travelers only-we do not accept local reservations.

Jan 17 – 24

R1,281 ZAR per night

Cottage in Polk City

4.85 out of 5 average rating, 199 reviews

Cozy Historical Cottage

This lovely cottage of 1,000 sqft of living space, two bedrooms, one bath, dining room. Enjoy the view from the patio overlooking the backyard or relax in the Florida room on a traditional swing. The Van Fleet Trail and Freedom Park are just a few yards away. Popular attractions like Fantasy of Flight, Dinosaur World, Lego Land, and Disney are nearby. The Lakeland Mall is 10 minutes away movies & restaurants. Just a short walk away you'll find two family restaurants. Book your stay today!

Oct 31 – Nov 7

R1,615 ZAR per night

Cottage in Lake Wales

4.88 out of 5 average rating, 108 reviews

The "Little ‘Toa" Ideal for short & long stays!

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

Mar 10 – 17

R2,483 ZAR per night

Home in Clermont

4.93 out of 5 average rating, 188 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow full disinfecting of the house.

Jul 10 – 17

R3,251 ZAR per night

Home in Babson Park

4.97 out of 5 average rating, 108 reviews

Authentic "Old Florida" on Crooked Lake!

Authentic "Old Florida" on Crooked Lake! Surrounded by palmettos and Florida foliage, our 1930's rustic lakehouse is serene, private, and exceptionally relaxing. Spring-fed Crooked Lake is designated an "Outstanding Florida Waters" lake and is great for swimming, paddle boarding, kayaking, fishing, and waterskiing. Huge screen porch, ping pong table, fully-equipped kitchen, dining room table for 12, spacious living area (great for games) -- you won't want to leave!

Jun 4 – 11

R5,528 ZAR per night

Guest suite in Kissimmee

4.86 out of 5 average rating, 567 reviews

Private Studio in POOL home

Hello! We offer a portion of our home with a King sized bed, a large private bathroom with a Jacuzzi tub, and a Harry Potter play area accessed by rock climbing wall. The mini kitchen has a microwave, bread toaster, coffee maker, and refrigerator. There's an internet TV in the apartment with access to Prime. The pool and garden areas are shared with my family and another set of travelers. We are happy to offer our studio with a 5-star cleanliness rating.

Jul 7 – 14

R1,433 ZAR per night

Townhouse in Kissimmee

4.92 out of 5 average rating, 227 reviews

Beautiful Farm House Decor near Disney, Sleeps 6

Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

Sep 18 – 23

R1,935 ZAR per night

Cottage in Kissimmee

4.96 out of 5 average rating, 421 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.

Sep 17 – 24

R1,873 ZAR per night

Home in Auburndale

4.94 out of 5 average rating, 146 reviews

Lake Whistler Beach House with lakefront pool

The Lake house is a resort with Paddle boards/Kayaks at no cost to our guests. Enjoy the entire yard and non-public lake with a private beach which offers you fishing and water sports (jet skis are additional). The main house has a pool table,air hockey and live darts! Also there is a BBQ, 4 TV's, cable, internet, movie library and washer/dryer, Pool and pool Jacuzzi. Small fenced back yard for pets (pet fee required).

Jan 2 – 9

R7,179 ZAR per night

Guesthouse in Lakeland

4.98 out of 5 average rating, 214 reviews

Modern lakeside retreat by SEU and FSC

This 1/1 lakefront historic cottage, built in 1920, is separate from the main house with its own entrance, parking, front porch & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks and fishing poles are provided for your enjoyment during your stay. Come unwind and enjoy the lake views from the hammock and private beach!

Aug 1 – 8

R2,099 ZAR per night

Vacation rentals for every style

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Popular amenities for Cypress Gardens family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Condo in Davenport

4.92 out of 5 average rating, 377 reviews

Mediterranean Resort! 2+2 Condo. 10 mins to Disney

Nov 9 – 16

R2,515 ZAR per night

Apartment in Davenport

4.86 out of 5 average rating, 243 reviews

Recently Award Winning Renovated 2+2 Near Disney

Sep 30 – Oct 7

R2,504 ZAR per night

Townhouse in Kissimmee

4.95 out of 5 average rating, 161 reviews

Beautiful family home near all attractions.

Jun 27 – Jul 4

R2,254 ZAR per night

Villa in Kissimmee

4.96 out of 5 average rating, 167 reviews

4 bed villa w/private pool near Disney, sleeps 6+

Aug 22 – 29

R2,907 ZAR per night

Condo in Champions Gate

4.85 out of 5 average rating, 262 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

Oct 8 – 15

R2,454 ZAR per night

Condo in Kissimmee

4.84 out of 5 average rating, 250 reviews

Lake View Family Condo Disney Universal Orlando

Apr 2 – 9

R2,172 ZAR per night

Townhouse in Kissimmee

4.95 out of 5 average rating, 251 reviews

Disney/Universal Home Away from Home!

Sep 14 – 21

R2,907 ZAR per night

Condo in Davenport

4.97 out of 5 average rating, 152 reviews

Disney Orlando Bahama Bay Resort Theme Parks &More

Nov 30 – Dec 7

R2,268 ZAR per night

Family- and pet-friendly home rentals

Home in Lakeland

4.82 out of 5 average rating, 130 reviews

Florida Lake View With Private Pool And Fishing

Nov 11 – 18

R4,464 ZAR per night

Home in Lakeland

4.91 out of 5 average rating, 121 reviews

Central Lakeland Home Convenient to Parks & Sports

Sep 10 – 17

R3,527 ZAR per night

Villa in Kissimmee

4.78 out of 5 average rating, 406 reviews

7BD with Movie Theater Pool & Jacuzzi near Disney!

Dec 5 – 12

R6,068 ZAR per night

Villa in Kissimmee

4.92 out of 5 average rating, 181 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

Feb 22 – Mar 1

R8,398 ZAR per night

Villa in Kissimmee

4.85 out of 5 average rating, 370 reviews

Amazing Cozy 4Bed/3Bath, Disney Area, Private Pool

Jan 17 – 24

R3,650 ZAR per night

Home in Kissimmee

4.89 out of 5 average rating, 177 reviews

PrivateJacuzzi-BBQ-ResortPool-Gym-7mlsDisney

Apr 2 – 9

R2,996 ZAR per night

Home in Kissimmee

4.89 out of 5 average rating, 145 reviews

Luxury Disney Vacation Home on Reunion Golf Resort

May 26 – Jun 2

R9,107 ZAR per night

Home in Clermont

4.86 out of 5 average rating, 117 reviews

Cozy Family Home near Disney

Oct 19 – 26

R2,618 ZAR per night

Family-friendly home rentals with a pool

Home in Kissimmee

4.84 out of 5 average rating, 205 reviews

3 bedroom Villa in Kissimmee

Apr 21 – 28

R2,278 ZAR per night

Home in Davenport

4.86 out of 5 average rating, 205 reviews

Disney World Area Villa Orlando * Pool * Sleeps 10

Sep 8 – 15

R2,909 ZAR per night

Cottage in Kissimmee

4.94 out of 5 average rating, 403 reviews

Entire cottage for 5, close to Disney, Universal!

Nov 13 – 20

R1,686 ZAR per night

Home in Davenport

4.93 out of 5 average rating, 200 reviews

Family pool villa - 20 minutes to Disney!

Nov 15 – 22

R2,541 ZAR per night

Home in Kissimmee

4.79 out of 5 average rating, 256 reviews

3 bedroom Orlando Florida pool home

Jan 13 – 20

R2,301 ZAR per night

Apartment in Kissimmee

4.92 out of 5 average rating, 319 reviews

Great Full Apartment. Just 5' from Disney Orlando

Sep 3 – 10

R2,183 ZAR per night

Cottage in Kissimmee

4.9 out of 5 average rating, 212 reviews

Be Our Guest Sandcastle Cottage 81

Oct 23 – 30

R1,858 ZAR per night

Tiny home in Kissimmee

4.94 out of 5 average rating, 328 reviews

Blue Bungalow Tiny House near all Attractions!!

Apr 21 – 28

R1,797 ZAR per night

Quick stats about vacation rentals that are family-friendly in Cypress Gardens

Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
20 properties allow pets
Total number of reviews
3.4K reviews
Nightly prices starting at
R1,485 ZAR before taxes and fees

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