Family-friendly vacation rentals in Lady Lake

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Top-rated family-friendly rentals in Lady Lake

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

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Guest favorite

A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.

Home in The Villages

4.95 out of 5 average rating, 124 reviews

2/2 custom pool home with 4 person gas golf cart

Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

Guest favorite

A spacious living room features light green walls and hardwood flooring. A large flat-screen television is positioned on a white media console. Natural light enters through multiple windows, illuminating a comfortable cream-colored sofa adorned with pillows. A coffee table sits centered on a patterned area rug.

Home in Orlando

4.88 out of 5 average rating, 207 reviews

Charming Orlando Cottage - Close to Everything!

This charming 1920's cottage is the perfect retreat for either a brief stay visiting all that Orlando has to offer, or could be a quiet escape to stay for a few months working remotely. The home has one king size and one queen size bed, a separate office if you are needing to work out of the home. It's a private space but on a larger piece of property that also has two other homes and shares access to a beautiful lake - which our guests are welcome to use! Inquire for different terms available.

Guest favorite

The cabin is surrounded by lush greenery, positioned on a private peninsula. A spacious deck with seating faces the water, offering a serene view of the canal. Natural light filters through the trees, illuminating the inviting structure.

Cabin in Floral City

4.97 out of 5 average rating, 128 reviews

Private Waterfront Cabin Retreat with Kayaking

Your private retreat on an acre nestled on a canal to the Withlacoochee River, wrapping around 2 sides of the property. Relax on your porch overlooking the water as you watch the birds and deer play. Kids will love the tire swing, toys such as Lego, Lincoln logs, pool table and ski ball. Kayaks available to our guests awaiting adventure. Bond around the fire pit, walk the trails, lounge in the hammocks, and fish on the dock. Setup the big screen to watch a movie. Welcome to your get-a-way!

Top guest favorite

A comfortable living area features a dark leather sofa, a wooden coffee table, and a dining table with chairs. Bright light filters in from the outdoor patio, revealing lush greenery and a seating area beyond the sliding glass doors adorned with a vibrant red umbrella.

Guesthouse in College Park

4.97 out of 5 average rating, 436 reviews

The Coach House- 2 bedroom/3 bath Orlando Getaway!

Pet-friendly 2 Bedroom/3 Bath House. Designed by renowned architect James Gamble Rogers II, the house is a 25-minute drive ($23 Uber) from the MCO Airport. Nestled in the heart of Orlando's College Park district, it is an oasis just moments away from Downtown Orlando: nightlife, museums, and funky art and music scene. Take a 25-minute drive into Disney, Universal, or The Outlets. Uber/Lyft/Walk to nearby trendy restaurants, museums, theaters, boutique shopping, and our craft beer scene.

Top guest favorite

A private pool area is surrounded by lush tropical landscaping, featuring tall palm trees and vibrant greenery. The sparkling blue water of the pool reflects the sky, while a paved pathway leads to the entrance. A serene atmosphere is created by the nearby plants and outdoor decor.

Home in Maitland

4.95 out of 5 average rating, 164 reviews

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Superhost

A rectangular pool is surrounded by a screened enclosure, offering a clear view of the turquoise water. The pool features built-in steps and railings for easy access, while smooth concrete provides a clean area around the perimeter.

Home in Inverness

4.78 out of 5 average rating, 114 reviews

3br POOL, Fenced, near Downtown & Trails

No Parties or Events!! 3 bedroom, 2 bathroom pool home close to downtown, parks, trails and race track. Big screen TV's, comfortable seating, memory foam mattresses, plenty of extra blankets and pillows, high speed internet & TV. The master bedroom has a king size bed, the two other bedrooms have queen sized beds. All beds have memory foam mattresses Conveniently located half a mile from Withlacoochee State Trail. A short drive to Crystal River and Fort Island Beach.

Top guest favorite

A wooden deck extends towards the river, featuring a set of black outdoor chairs and tables. Lush greenery surrounds the water, while kayaks rest along the bank. A covered seating area is visible to the left, offering a shaded spot to enjoy the natural setting.

Home in Dunnellon

4.96 out of 5 average rating, 151 reviews

Palm Waters Riverhouse

Peaceful, pet-free 4/3 family getaway or work retreat on the a quiet part of the Rainbow River. Nestled in nature but minutes from restaurants, grocery and antique stores. Relax on the dock, expansive deck, screened porches or around a camp fire. Abundant outdoor activities including tubing, paddling, fishing, snorkeling, biking, etc. Pls note, 10 people max. For parties of 7+, there is a fee to unlock the 4th bedroom. No pets, no smoking, no parties or events.

Top guest favorite

A serene lakeside view showcases a sandy beach area, with canoes and a pedal boat resting on the shore. The tranquil water reflects the surrounding greenery and a wooden dock can be seen in the distance, inviting guests to enjoy outdoor activities.

Cabin in Ocklawaha

4.98 out of 5 average rating, 184 reviews

VERY BEARY CABIN on Crystal Lake

Bring Fido only $25 per stay/Whole House "Very Beary Cabin" is a 2100 Sq Ft split level nature lodge style cabin plus glamping A Frame on natural spring fed, sand bottom Crystal Lake and it is a Certified Wild Life Habitat. Fully renovated in a knotty pine cabin bear theme. It includes private lower level lockout "Outdoorsman's Suite", a total of 3 bedrooms plus pullout. Plus a bonus Glamping A Frame "The Cub House" is included on the property with all stays.

Guest favorite

A charming home is presented with a light blue exterior and a welcoming front porch. Lush greenery and potted plants adorn the entrance, while an inviting pathway leads to the front door. A single-car garage is visible to the right, framed by trees and bright skies.

Home in Mount Dora

5 out of 5 average rating, 167 reviews

UPSCALE DOWNTOWN VINTAGE 3/2 HOME

*SPECIAL SUMMER RATES* 2 blocks from downtown boutiques, restaurants, museums, parks, marina, etc. in historic downtown Mt. Dora. Newly renovated home with fully equipped kitchen w/granite bar & stainless appliances; a/c sun porch w/dining; large master suite with King; 2nd BR with Queen and central bdrm/study w/desk & daybed (2 twins); 55" and 32" flat screen TV''s, cable & WIFI; Laundry room w/washer and dryer; Rear outdoor patio.

Guest favorite

A charming yellow house with a distinctive star on the door is framed by large, shaded trees. A concrete path leads to the entrance, flanked by a low wooden fence, creating a welcoming approach. Moss hangs gently from tree branches, adding to the serene ambiance.

Bungalow in Mount Dora

4.91 out of 5 average rating, 310 reviews

Historic! Ladybug Bungalow in Downtown Mt. Dora

My place is close to Downtown Mount Dora and all the amenities of the beautiful waterfront historic city. You’ll love my place because of the proximity to downtown Mt. Dora - a quick walk. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends. $75 pet fee per pet. (2 pets max) Payment request will be sent after booking. This will help to keep Ladybug a pet friendly home!

Top guest favorite

The two-story house features a light grey exterior with black shutters and a welcoming entryway. A decorative red star is positioned above the door. A small patio area with a table and two chairs is located under a covered porch, surrounded by green grass and landscaping.

Cottage in Tavares

4.95 out of 5 average rating, 110 reviews

Eagles nest

This 1600 Sq foot two story house was recently remodeled with new paint, flooring, appliances and furnishings. The house is not child proof and therefore do not accept children under the age of 12. Downstairs consists of a kitchen, half bath, family room with dining room table and large screen TV. Upstairs is a spacious master bedroom with sitting area and TV and large closet, second bedroom, study and full bath with tub.

Guest favorite

A stone pathway meanders through lush greenery, leading towards a serene seating area. Tall palmetto plants are situated on either side of the path, with vibrant seating visible in the background. Sunlight filters through the surrounding foliage, creating a peaceful invitation to relax outdoors.

Cottage in Brooksville

4.94 out of 5 average rating, 460 reviews

Whispers of Country Where your soul will Wander.

The Shebeen – a charming retreat nestled along the Brooksville ridge, on a picturesque working dairy farm. Here, adventure meets relaxation in a space designed for, reflection, and a bit of romance. Let the rhythmic sound of the farm surround you as you step into a world where time slows, and every moment feels like a sweet escape. Book your stay now and find a little magic in every moment.