Holiday houses in Lady Lake

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Top-rated holiday rentals in Lady Lake

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
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
4.96 out of 5 average rating, 141 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

Top Guest favourite
A decorative entrance sign for Villa De La Vista South is set against lush greenery and vibrant flowering plants. The sign stands prominently atop a circular flower bed, with a clear blue sky and soft clouds in the background.
Home in The Villages
4.95 out of 5 average rating, 19 reviews

Charming Villages Retreat

Charming 2B/2B Cottage Villa near Sumter Landing and Spanish Springs Escape to this beautifully updated villa in The Villages. Enjoy a designer kitchen, cozy living room with sectional and 75” TV, and French doors leading to a screened lanai. The private, fenced courtyard is perfect for relaxing under party lights. The master suite includes a walk-in closet and blackout shades. Explore with the included golf cart, access 50 golf courses, 100+ pickleball courts, pools, and nightly entertainment.

Top Guest favourite
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.
Home in Lady Lake
4.96 out of 5 average rating, 340 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.

Guest favourite
An exterior view of a home features a golf cart parked in the driveway, along with a glimpse of the garage entrance. The porch includes a potted plant, and the front windows display shutters. Circular insets showcase the dipping pool, pool table, and foosball table.
Home in Lady Lake
4.88 out of 5 average rating, 17 reviews

•Hot Tub & Golf Cart - Courtyard Villa•

Our newest 5 Star ⭐ listing with a heated swim spa (additional fee) & golf cart in the heart of Spanish Springs minutes from everything you’ll need. Enjoy the town squares, live music, bars, golf and much more 🎶 The home has a dipping pool/spa that has swim jets that allows you to swim against for exercise. Enjoy the outside courtyard with a BBQ and patio furniture Home in the heart of The Villages, a 7 min golf cart ride from Spanish Springs, 15 min from Sumter Landing, Brownsville-30min

Guest favourite
The private pool area is enclosed by a screened lanai, illuminated by string lights. A relaxing area features loungers beside the pool, with a raised spa and gentle water feature. Lush greenery surrounds the space, creating a serene atmosphere.
Villa in Lady Lake
5 out of 5 average rating, 24 reviews

Heated Pool Golf Cart Dog Friendly in The Villages

Nestled amidst lush greenery ,Vida Rosa’s private pool provides a serene outdoor oasis, complete with a dining area, loungers, and a gas BBQ. The luxurious accommodations are thoughtfully designed to evoke a sense of calm and elegance. Conveniently located, just a short golf cart ride away from the squares of Spanish Springs & Lake Sumter offering a variety of entertainment etc. Note: The pool has a jet tub attached to it. The water temperature is the same temperature as the pool, 86 .

Top Guest favourite
Home in The Villages
4.91 out of 5 average rating, 23 reviews

Outdoor Fun at the Pool + 2 Golf Carts!

Welcome to this POOL home with 2 GOLF CARTS! Spacious and inviting. UPGRADED WHITE cabinetry, extended DOUBLE PANTRY, GRANITE countertops. PLANTATION SHUTTERS. Featuring a large pool surrounded by an expansive deck and birdcage. Located near Spanish Springs Town Square and Lake Sumter Landing; Close to Tierra Del Sol Country Club and Championship Golf Course; Hacienda Championship Golf Courses, and Hacienda Regional Recreation Centers. No cats. Dogs under 20 lbs allowed with pet fee.

Top Guest favourite
A comfortable living area features a light-colored sectional sofa and a textured rug. A wall-mounted television is positioned above an elegant gray console table adorned with small potted plants. Soft lighting is provided by pendant lamps, complemented by natural light from a nearby window.
Home in Lady Lake
4.95 out of 5 average rating, 83 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!

Top Guest favourite
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.
Home in Lady Lake
5 out of 5 average rating, 56 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.

Top Guest favourite
Home in Lady Lake
5 out of 5 average rating, 49 reviews

Villages Retreat Includes Golf Cart & Amenities

Wake up, grab the golf cart, and tee off. This upgraded 2BR/2BA home puts you at the center of The Villages lifestyle — with two included Lifestyle IDs giving you full resident access to 41 executive golf courses, sports pools, pickleball, tennis, and nightly entertainment at the town squares. Inside, enjoy walk-in showers, adjustable queen beds, a modern kitchen, electric fireplace, and large smart TVs. Florida’s Friendliest Hometown is yours to explore.

Top Guest favourite
Guesthouse in Lady Lake
5 out of 5 average rating, 229 reviews

Cute & Cozy Tiny Guesthouse

Take it easy at this cozy and peaceful getaway located in a safe and quiet neighborhood near The Villages. It's conveniently located all within 1.5 miles to Walmart, Aldi, Waffle House, McDonald's, Pizza Hut, Cracker Barrel, BJ's Wholesale and many other shops and restaurants. Plus, The Villages Hospital. We are also located two miles from The Villages Spanish Springs town square which has free entertainment from 5pm to 9pm every night of the week.

Top Guest favourite
A single-story home is seen with a light gray exterior, framed by a large tree in the front yard. An American flag is displayed on the porch, and a white truck is parked in the driveway. Lush green grass surrounds the house.
Home in The Villages
5 out of 5 average rating, 13 reviews

perfectly located Villages home

Located a 4 minute cart ride from Spanish Springs village center. Electric 2 seater Golf cart. Only 2 miles from Lake Sumter Landing village center. Nearby pools, golf, pickle ball, tennis, shuffleboard, 365 evening-a year live music. 7 day minimum stay. Publix, Winn Dixie, pharmacy, liquor store, barber, all within a mile (5-6 minute) cart ride. Host will obtain guest pass to allow pools, golf, pickleball, etc. $50 extra charge to guest(s).

Top Guest favourite
Home in Lady Lake
4.98 out of 5 average rating, 50 reviews

Relaxing House in The Villages

Relax with the whole family at this peaceful place to stay. Open concept spacious vacation home with easy access to endless options for entertainment and restaurants. Located in the Historic District of The Villages there is something to do for the whole family!

Popular amenities for Lady Lake holiday rentals

When is the best time to visit Lady Lake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$211 NZD$228 NZD$206 NZD$183 NZD$171 NZD$156 NZD$144 NZD$149 NZD$157 NZD$166 NZD$181 NZD$195 NZD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • How much does it cost to stay in farmstay rentals in Lady Lake?

    Experience the best of Lady Lake with our farmstay rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Lady Lake?

    Yes! Work meets play with ease at over 90 vacation rentals in Lady Lake featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Lady Lake?

    Lady Lake has more than 110 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Lady Lake?

    Four-legged friends are welcome in Lady Lake. Choose from more than 90 vacation rentals for guests traveling with pets.

  • Are there Lady Lake house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Lady Lake, available on Airbnb. Make a splash and soak up the sun in style!

  • Do villa rentals in Lady Lake have wifi?

    Absolutely! We offer over 10 villa rentals with wifi in Lady Lake. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lady Lake have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Lady Lake. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lady Lake have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Lady Lake. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Lady Lake

  • Total holiday rentals

    Explore 170 holiday rentals in Lady Lake

  • Nightly prices starting at

    Lady Lake holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,660 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Lady Lake holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Lake access, Gym and BBQ grill across Lady Lake rentals

  • 4.9 Average rating

    Lady Lake stays are highly rated by guests—averaging 4.9 out of 5!

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