Kid-friendly holiday rentals in The Villages

4.96 out of 5 average rating, 313 reviews

Home in Lady Lake

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

4.94 out of 5 average rating, 141 reviews

Remodeled 2/2 Baja style villa w/4 person cart

4 person, yamaha gas golfcart offered at this baja style 1000 sqft 2BR, 2BA courtyard villa! It comes fully furnished with pots, pans, linens, and does have a blow dryer and keurig! located in the De La Vista South area just off Morse, this villa is just a short cart ride to Spanish Springs or Sumter Landing. The villa has new stainless appliances, beautiful plank flooring, and fresh paint. King bed in the master, queen bed in the guest bedroom. All bedrooms have smart TV's, cable in LR only

4.95 out of 5 average rating, 120 reviews

Apartment in Belleview

Solomon's porch entire apartment

Solomon's porch apartment is entire private 350 st ft apartment with bedroom, kitchenette, your own hallway and private bathroom. Solomon's porch apartment attached to main house.We are small Christian family that loves bible proverbs and named Airbnb after Solomon's wisdom. We have other listing that we are hosting since 2022. Our brand new house located between Ocala and The Villages. We are only few minutes from Santos mountain bike trails, horse park, National Forest and Silver Springs.

4.95 out of 5 average rating, 20 reviews

Cheerful King Bed Home in the Villages

Welcome to your perfect getaway in The Villages! This charming 2-bedroom, 2-bathroom home is ideally located for you to enjoy all the best amenities the area has to offer. Fenney Pitch and Putt is nearby, offering a fun and relaxing experience. The Sugar Cane Recreation Center, with its beautiful walking trail & adult pool is perfect for leisurely days under the sun. Also nearby is the popular Fenney Grill, with a resort style family pool, you can enjoy delicious meals and refreshing drinks.

4.96 out of 5 average rating, 163 reviews

Home away from home entire house

Located in an excellent area in the Chatham neighborhood, of the Bromley villas. This home offers easy access to restaurants, shopping and recreation. For nightly entertainment you're a short distance away from Lake Sumter land and Spanish Spring town Square where you will find many restaurants, grocery stores and free nightly live entertainment. This home is fully equipped with everything you need. Pets are allowed. Recreational guest passes included. Golf cart not included with reservation.

4.98 out of 5 average rating, 112 reviews

Private 2/2 Villa w/ New 4 Seat Gas Golf Cart

Relaxing home in quiet neighborhood w/ private yard, screened porch - rare in The Villages! Roanoke Retreat is a beautifully remodeled 2 bed/2 bath home - only 15 minute golf cart ride to Spanish Springs, 20 minutes to Sumter Landing . Rental includes 4 seat gas golf cart w/ access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in every room, fully equipped kitchen, new BBQ grill. 55+ community but no age restriction to visit

4.93 out of 5 average rating, 133 reviews

Pool, golf cart, private backyard. Paradise!

Come and enjoy this relaxing piece of paradise surrounded by lush greenery with your own, small, private pool (not heated). "Serene on the Green" is a beautifully remodeled 3 bedroom, 2 bathroom designer home (1,536 sqft) with a large screened outdoor pool area with lots of privacy. Our location 320 steps from the Santiago Recreation Complex with two golf courses and a short ride to Lake Sumter Landing and Spanish Springs is perfect. A new custom 2021 Yamaha QuieTech golf cart is included!

4.99 out of 5 average rating, 116 reviews

VIEW-T-FUL! w/Golf cart

Stunning entry with one of a kind picturesque setting and unbeatable location all in one. This lanai was redesigned with no support columns to have this spectacular highly desirable panoramic golf front & water view. Sweeping view of Southern charm, cluster of mature oak trees with Spanish moss. The back of the home facing the morning sunshine lighting up the lanai and screen area for a fine morning of relaxation. Don't hesitate, this home has it all, golf cart too!

Superhost

4.86 out of 5 average rating, 122 reviews

Patio Villa, 5 mins from Sumter, FREE Gas Cart!

Adorable Patio Villa in a Prime Location. FREE GAS GOLF CART! Located in the heart of The Villages, in the village of Caroline. 5 minutes from Lake Sumter Landing, with bountiful options for golf, food, and entertainment just a short golf cart ride away. This isn’t your average, ‘bare bones’ investment rental. This is where our family stays when they come to visit. It is furnished with quality linens, furniture, kitchen equipment, Xfinity, & Roku.

4.98 out of 5 average rating, 41 reviews

Great location w/ golf cart! Lake Sumter-Brownwood

This home greets you with a driveway Pelican painting, amazing landscaping and a decorative glass entry door. Savanna shutters and comfortable furniture throughout the home. 12 minute golf cart ride to Lake Sumter and 17 minutes to Brownwood Square. Use the included golf cart to get there! Sea Breeze Rec Center with pool, pickleball, etc. is just a few minutes away. Grocery stores closeby. Quiet neighorhood. Dogs under 25 lbs allowed.

Superhost

New place to stay

The Villages Vacation Haven- Golf Cart Included!

Stay in the heart of The Villages, just minutes from Brownwood Square and top-rated golf courses! This charming home offers a short walk to Manatee Family Pool, and easy access to dining, shopping, and entertainment. Relax in a well-appointed space with modern amenities and a private patio. Whether you're here for tee time, exploring the local attractions, or unwinding in Florida’s sunshine, this vacation haven is perfect for your getaway!

4.95 out of 5 average rating, 126 reviews

Villages-Private Heated Pool-Central Location

Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses

Holiday rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for The Villages kid-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Child-friendly house rentals

5 out of 5 average rating, 18 reviews

Central Villages w/ Golf Cart

JenieneRating, 5 stars3 weeks ago

absolutely beautiful place! the beds are a little harder than what I have at home but we may do since it was only two nights. I love the fact that they were adult only pools very close to the house! some wonderful restaurants around as well as live music every night! we had a wonderful time

5 out of 5 average rating, 9 reviews

Best of The Villages! 2BR/2BA Home with Cart & Am

JodieRating, 5 stars2 months ago

The home was very nice and welcoming. It was a nice and quiet location with friendly neighbors.

4.95 out of 5 average rating, 20 reviews

2/2 Florida Chic Patio Villa !

JulianneRating, 5 stars3 weeks ago

Their home ranks among the best I have ever stayed at! Two king sized beds, hotel quality linens, tasteful decor, and Spotlessly CLEAN.

4.95 out of 5 average rating, 19 reviews

Brewed Awakening

JimRating, 5 stars6 months ago

It is a great space for a group, and the location is fabulous.

4.85 out of 5 average rating, 34 reviews

Beautiful Designer Home in The Villages Fl

5 out of 5 average rating, 22 reviews

The Palms. Luxurious, pool, golf/bird pond view

4.79 out of 5 average rating, 89 reviews

Carlton Courtyard Villa - Walk to Sumter Landing

5 out of 5 average rating, 16 reviews

Heated Pool, Dog Friendly, Golf Cart Included

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Kid-Friendly apartment rentals

4.96 out of 5 average rating, 115 reviews

Apartment in Ocoee

Completely Private and Cozy Studio

CamilleRating, 5 stars4 days ago

Lovely stay. Everything was very close and convenient. Everything was clean and cozy.

4.93 out of 5 average rating, 342 reviews

Apartment in Sorrento

Quiet Neighborhood in the Country

YarleneRating, 5 stars1 week ago

The person in charge very attentive and willing to help in whatever is necessary flexible and very accessible entrance. Very clean place, super clean pool and very cosy place. Very quiet neighborhood.

Apartment in Winter Garden

4.96 out of 5 average rating, 262 reviews

Lakeview Garden Studio

GraciRating, 5 stars2 weeks ago

This was our third stay with Leah, and like the other two times we really enjoyed the apartment! Close to the amusement parks, great restaurants and coffee shops. The apartment was very clean and had everything you needed including products you might’ve forgot or even snacks to enjoy. We truly do find this apartment comfortable and peaceful, we can’t wait to come again soon!

Apartment in Winter Garden

4.9 out of 5 average rating, 147 reviews

Stay A While

PaulRating, 5 stars3 weeks ago

This is the second time my wife and I stayed here and both stays were exceptional. The place is clean, with beautiful views of the farm with horses. Quiet, with all amenities needed, and a beautiful pool that we enjoyed... we would happily recommend this place and the next time we are in the area, we would gladly book this place again!

Apartment in Ocala Historic District

5 out of 5 average rating, 227 reviews

Treehouse apartment set among the big daddy Oaks

LeslieRating, 5 stars1 month ago

I enjoyed another wonderful stay at Joyce's place (my third stay). As always, great communication and very clean and welcoming space. The neighborhood is top notch for an easy walk to historic downtown, while residing in a tranquil tree layered oasis.

Superhost

Apartment in Clermont

4.79 out of 5 average rating, 273 reviews

Charming Lakefront Apt. Near Disney

EsmeraldaRating, 5 stars1 week ago

I had a wonderful stay in Clermont! I stayed here for a little solo getaway and it was exactly what I needed. Super peaceful, quiet, and the view was honestly so pretty. Everything was clean and comfy, and I just felt really relaxed the whole time. It was the perfect spot to take a breather. I would totally come back again!

4.93 out of 5 average rating, 481 reviews

Apartment in Brooksville

Emerson Place Garage Apartment

BenRating, 5 stars4 days ago

We will stay here again when in the Brooksville area. Such an amazing historic place. The stairs are steep, so if you are not confident on your feet you might want a different place. The neighborhood is excellent and quiet. Walk to restaurants. Very clean. We love this place. I could live here. Wide open space, lots of little extras like snacks and coffee. Great value for the money.