Holiday houses in Lady Lake

A bright yellow door features a decorative wreath made of colorful flip-flops and a large floral element. The door is framed by clear glass panels, with the words 'home sweet home' artfully displayed near the doorknob.

4.94 out of 5 average rating, 90 reviews

Magnolia Cottage under the Paradise sun.

Stay in my quiet neighborhood 1 hour/ 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! Roku TVs are located in the living room & bedroom. Log into your favorite apps. Take a bike ride on the bicycles. For your convenience there is a grill, laundry & free parking,

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.

4.96 out of 5 average rating, 134 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

5 out of 5 average rating, 19 reviews

An open living space features a cozy sleeping area and a small dining arrangement. Wooden beams highlight the ceiling above. Natural light enters through the door and windows, while a television and kitchenette with appliances are visible against the walls.

Apartment in Lady Lake

Desperado 2 - Cozy Peaceful Apt. Lady Lake FL.

Escape to your unique and private 2nd story apartment nestled on 2 acres of serene land and just a short 7-minute drive to The Villages. Enjoy the tranquility of nature while still being close to vibrant entertainment, shopping and dining options. Your cozy and well appointed space offers the perfect blend of seclusion and convenience making it an ideal getaway for relaxation and rejuvenation. *perfect for vacation *perfect for traveling workers *perfect for visiting family in the The Villages

A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.

4.96 out of 5 average rating, 325 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.

The exterior of a single-story home is framed by three tall palm trees, set against a clear blue sky. A well-maintained lawn surrounds the entrance, which is highlighted by a neatly paved driveway and a two-car garage. The inviting front door features a large window.

5 out of 5 average rating, 24 reviews

The Mulligan House-The Villages

BRAND NEW Golf-Front Furnished Home for rent- "Million Dollar View" This 3 bedroom 2 bathroom home sits on the 18th fairway of Orange Blossom Hills Championship Golf Course!! Enjoy panoramic GOLF COURSE VIEWS from the Great Room. Kitchen, Screened Lanai and from your Master Suite. Located within WALKING DISTANCE from the Orange Blossom Hills Country Club with its RESORT STYLE POOL. A short golf cart ride over the bridge brings you into Spanish Springs with Shopping, Dining and entertainment.

A single-story home showcases a light-colored exterior and a welcoming front porch, bordered by a white picket fence. Neatly trimmed shrubs and grass surround the home, adding to the cheerful curb appeal. A paved driveway leads to a garage on the right.

4.95 out of 5 average rating, 170 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.

The modern home features a spacious driveway leading to a large carport and a two-car garage. A covered porch with steps provides access to the front entrance, surrounded by greenery and trees.

5 out of 5 average rating, 49 reviews

Villages home with unique elevated front porch

A bright 2 bed, 2 bath home with new flooring throughout, includes golf cart. Located in historic Country Club Hills. Less than two miles from Spanish Springs Square with restaurants, shops & FREE nightly entertainment. Minutes away from pools, hot tubs, recreation centers, walking paths, & golf courses. Fully equipped kitchen with starter pack. Relax with a book & a drink on the breezy front porch with an overhead fan. Free Netflix, Peacock Premium & high speed internet. No checkout chores.

A cozy living area is presented with dark leather sofas and matching armchairs. A round ottoman sits centrally, complementing the layout. Soft lighting from ceiling fixtures illuminates the space, while a decorative piece of art and potted plants add subtle elegance.

5 out of 5 average rating, 40 reviews

Villages Retreat Includes Golf Cart & Amenities

Charming retreat in The Villages. GOLF CART INCLUDED w/ requirements & limitations see below. Our 2BR/2BA offers upgrades including walk-in showers, adjustable queen beds, modern kitchen, e-fireplace, & large TVs. You'll have access to a wealth of amenities, free golf on 41 executive courses to refreshing pools, tennis, pickleball, & more. The Villages charges a $50 fee for the two lifestyle IDs. Please book your stay with us, & experience luxury living at our vacation rental in The Villages

Superhost

A tranquil sunset reflects off the calm lake surface, displaying hues of pink and purple in the sky. Outdoor seating is provided on a deck, with a dining table set against the serene backdrop of the water and surrounding trees.

4.89 out of 5 average rating, 19 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

4.85 out of 5 average rating, 104 reviews

An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.

Villa in The Villages

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.

A single-story home is presented with a soft beige exterior and a welcoming entrance. The front yard is neatly landscaped with green grass and low shrubs. A large tree provides shade, and a double garage is visible on the left.

4.94 out of 5 average rating, 17 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!

The open living area showcases a cozy red sofa facing a large TV mounted on the wall. A sleek kitchen bar with three red stools is situated nearby, and a chair with a patterned design complements the modern decor. Natural light is visible from an entrance.

4.91 out of 5 average rating, 54 reviews

The Villages, De La Vista West 1762

* Just available, complete renovation/new everything of this Patio Villa. * Considered one of the best locations, right in between Lake Sumter Landing and Spanish Springs squares, close to main intersection of CR466 and Morse Blvd. * Over-sized lot on street end, no homes behind, mature trees and 3 outdoor entertaining areas. *January, February and March are only rented consecutively.

Popular amenities for Lady Lake holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Lady Lake

5 out of 5 average rating, 30 reviews

A single-story vacation home is presented with a light exterior and a neatly maintained front yard. A white picket fence encloses colorful landscaping, while a spacious driveway leads to a two-car garage. Clear skies enhance the inviting curb appeal of the property.

Home in Wildwood

Opal Oasis in The Villages

The exterior of the home displays a well-manicured front yard with decorative plants and a white picket fence. A paved driveway leads to a two-car garage featuring a symmetrical design, accompanied by a clear blue sky above.

4.96 out of 5 average rating, 89 reviews

King Bed, Small Dogs OK, and 4-Seater Golf Cart!

Superhost

A sunroom filled with natural light features large windows showcasing greenery outside. A wooden dining table with four chairs sits alongside a comfortable seating area with cushions. Colorful decor elements include a floral area rug and decorative lamps, creating a welcoming atmosphere.

5 out of 5 average rating, 3 reviews

A designer 2 bed/2 bath home near Spanish Springs

An outdoor view of the home's exterior is presented, featuring a silver golf cart parked on a concrete driveway. The well-maintained front yard includes a white picket fence and landscaped areas with shrubs. A spacious garage is visible in the background under a clear blue sky.

4.91 out of 5 average rating, 57 reviews

Stunning Villa 2B/2B With Golf Cart

The exterior of a single-story villa features a light grey façade with a one-car garage and a well-maintained front yard. A white picket fence surrounds the property, complemented by tidy landscaping and a concrete driveway leading to the garage.

4.93 out of 5 average rating, 30 reviews

Delightful 2 bed/2 bath villa!

A heated saltwater pool is highlighted under a screened enclosure, with ambient lighting creating a calming atmosphere. Patio seating is arranged around the pool, and views of the adjacent living area are visible through expansive windows, enhancing the inviting indoor-outdoor connection.

5 out of 5 average rating, 35 reviews

Pirates & Parrots - The Villages - w/Golf Car !

A spacious living area is visible, featuring large windows that overlook the golf course. A decorative plant sits atop a glass coffee table, surrounded by comfortable seating in patterned upholstery. Natural light fills the room, enhancing the open and airy feel.

5 out of 5 average rating, 16 reviews

The Villages, Green View Cottage, in Silver Lake.