Family-friendly holiday rentals in Lady Lake

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

Getaway on the Waterway: Kayak, SUP, fish, relax!

Welcome to your peaceful Getaway on the Waterway right on the beautiful canal that connects Big and Little Lake Weir! Kick your feet up and wave at the boats going by as you grill or fish from the dock. Play a round of corn hole, hop on one of our paddleboards or kayaks for beautiful ride to either lake! Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, (they also offer sunset cruises and water taxi service to Eaton's Beach restaurant right from our dock!) RELAX and ENJOY!

3/2 w/ Two Golf Carts (6 seats), ~1 mile Sumter

Remodeled 3 bed (sleeps 6), 2 bath home in The Villages, only ~1 mile to Sumter Square! Screened patio backs up to 6 acre lot, very private except the cows! Rental includes access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Free use of 2 gas golf carts (4 +2 seats) to get to it all! Newly furnished home includes 5 smart TV's, including on patio, fully equipped kitchen, BBQ grill and more. Bedrooms include 1 king, 1 queen and 2 full beds.

Countryside Loft at Coco Ranch

Make memories with the ones you loves at this unique Countryside loft feeling cottage with an elegant mix between rustic and modern aesthetic. We are a pet friendly Cottage, bring your furry friend and enjoy the coziness. This is a family wood gated compound. Each cottage are private, surrounded by beautiful común areas. Surrounded by a lot of natural springs and also the convenients of local restaurants like “Gators Joes Beach Bar & Grill” at just 6m walk, 6m walk to Lake Weir, and more.

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.

JoMo Retreat on the Withlacoochee River!

JoMo property, a gem by the Withlacoochee River's side, where nature's beauty and tranquility coincide. A guest house just a stroll away from the canal's embrace, leading to the river, a serene and peaceful space. Canoes, paddle boards, and kayaks await, to explore the river, a water lover's favorite. World Equestrian Center and Rainbow Springs are a mere twenty minutes away. JoMo offers a nature-filled stay. Escape the hustle, in nature's embrace, at JoMo property, find your tranquil space.

Whole House-sleeps 10 The Villages Spanish Springs

Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

Majestic cabin on Fort Brook Farm

Get away from it all when you camp under the stars on our beautiful little farm. Our cabin is a bedroom with queen size bed and a sleeping loft that is a twin. Bring a sleeping bag for loft. This air conditioned and heated cabin has a little extra. There’s a sink, fridge, and a coffee maker with pods in the kitchenette. There’s a great fire pit that also is a grill. We have chairs and table to sit by your camp fire. The restroom and showers are separate. There is not a half bath in the cabin.

Beautiful House On the River, Kayaks, Large Dock!

Come relax by the river in this 3-bedroom, 2-bathroom vacation rental in Lady Lake, Florida. Recently built by our family in 2022, the home has a screened in back porch, a fire pit, WIFI, and is complete with a large private dock right on the Ocklawaha River. All that and it's located only 10 minutes from The Villages where you can shop and have fun. Centrally located 1-1/2 hours from Disney, Daytona beach, and Tampa. Lockbox key access is available for check-ins at any time of day.

Safari themed private addition with pool/hot tub.

This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

Location Can’t be Beat! With cart!

Experience The Village's retirement community lifestyle! The patio villa is located near Spanish Springs Town Square and the shopping corridor, where you will find nightly entertainment, dining and shopping. Walk to Savannah Center & Glenview Country Club. Your rental includes the complimentary use of a Yamaha gas golf cart and Guest ID cards that provide you access to our recreation facilities. Monthly guests may purchase Resident ID cards ($50) that include free executive golf.

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.