Holiday rentals in Lady Lake

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Top-rated holiday rentals in Lady Lake

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Top guest favourite

Home in Lady Lake

5 out of 5 average rating, 30 reviews

Ranch Retreat~10 beds~New

This ranch retreat home is perfect for large groups with plenty of parking. Perfect for celebrations, family gatherings, and even corporate or church events. Located on a large parcel of land in Lady Lake, FL, this home offers a quiet and secluded location that is centrally situated near the Villages and Chain of Lakes. We are 5 minutes away from Lake Griffin boat ramp, minutes away from Lake Griffin State Park, within 15 minutes of Venetian Gardens/Ski Beach and Lake Harris, and Eatons Beach.

Top guest favourite

Home in Lady Lake

4.96 out of 5 average rating, 313 reviews

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.

Top guest favourite

Home in The Villages

4.94 out of 5 average rating, 142 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

Guest favourite

Home in Lady Lake

4.87 out of 5 average rating, 31 reviews

Orange Blossom Golf 2B/2B, located in The Villages

Rolling hills and scenic views are exactly what you'll find in The Village of Country Club Hills. This beautiful home is centrally located in the historic area of The Villages within a five minute golf cart ride to The Orange Blossom Hills Golf and Country Club. Residents here can choose between 18 holes of championship golf, or the scenic Hilltop executive course. Close to shopping, restaurants, and nightly live music in the Spanish Springs Square. An hour drive from Orlando. 200 mbps Wifi.

Top guest favourite

Flat in Belleview

4.94 out of 5 average rating, 121 reviews

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.

Top guest favourite

Home in The Villages

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

Top guest favourite

Home in Lady Lake

4.94 out of 5 average rating, 85 reviews

Magnolia Cottage under the Paradise sun.

Stay in my quiet neighborhood 1 hour and 15 minutes from Disney. Enjoy the country club pools. Just five minutes away listen to free music every night at Spanish Spring Town Square. Restaurants & shopping are also minutes away. For your enjoyment there are recreation centers, golf courses & sports courts. Pickleball anyone! New Roku TVs are located in the living room & bedroom. Take a bike ride on the bicycles. For your convenience there is a new grill, laundry & covered free parking,

Superhost

Home in Lady Lake

4.85 out of 5 average rating, 13 reviews

Lakeside Retreat

Take it easy at this unique and tranquil getaway. Next stay in The Villages, why not stay on the lake? Enjoy lake view from open great room with updated kitchen with island, dining area, and living room. Enjoy lake view from master bedroom with dual vanities and walk in shower. Enjoy lake view from climate controlled Florida room off bedrooms. Enjoy lake view from deck off great room, patio with firepit, bbq grill, and dining table. Minutes from shopping, dining, entertainment

Top guest favourite

Home in Lady Lake

4.96 out of 5 average rating, 76 reviews

Villages, FL. Designer Home 2 blocks from town SQ!

Location!Location! Location! Designer home with access to close shopping,pools, tennis, golf, pickle ball, live bands every night, and it’s all within 5 minutes on golf cart! High speed Wifi. Grocery stores are 2 blocks from house! Golf cart is included with house. The house is located one hour north of Orlando, and 1 hour and 9 minutes away from Disney World! There is so much to do here in The Villages you can find something of interest for everyone in the family! Enjoy!

Superhost

Home in The Villages

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.

Guest favourite

Home in Summerfield

4.88 out of 5 average rating, 97 reviews

Cozy 2 bedroom home near The Villages

This hidden treasure is conveniently located next to The Villages. Enjoy a well kept, updated single wide mobile home in a spacious lot. The fenced in yard is perfect for children and pets to run and play. Relax in the screened in porch and take in the peaceful neighborhood surroundings. Just a short jog from Lake Weir where you can enjoy fishing, boating and swimming. Take a day trip to Orlando and Tampa attractions, Daytona and Cocoa beaches.

Top guest favourite

Home in Lady Lake

5 out of 5 average rating, 11 reviews

Orchid Greens Getaway

Nestled on a picturesque course in the villages, Orchid Greens is your gateway to a tranquil vacation. This charming home offers a private patio and bar area that is perfect for relaxing and watching the golfers go by. You will have easy access to the best shops and restaurants in the villages as the we are located 5 minutes from Spanish springs! This is the perfect home for a family of 4 or 2 couples traveling for some leisure games of golf!