Pet-friendly holiday rentals in Lady Lake

4.98 out of 5 average rating, 127 reviews

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.

4.96 out of 5 average rating, 355 reviews

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

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 villa is depicted, featuring a light-colored stucco facade and a two-car garage. Paved driveway curves towards the entrance, with decorative landscaping including a potted plant and stone accents. Windows are adorned with decorative arches, enhancing curb appeal.

4.95 out of 5 average rating, 165 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

4.99 out of 5 average rating, 146 reviews

A scenic view of a tranquil canal is presented, bordered by lush greenery. A wooden dock extends into the water, accommodating a boat. Nearby, comfortable outdoor seating is available, surrounded by natural landscaping, offering a peaceful outdoor space.

Home in Summerfield

Getaway on the Waterway- Dock+Kayaks+SUP board

Welcome to your peaceful Getaway on the Water. Whether you or your group are visiting the Villages, or just need a peaceful getaway to recharge, this is the place!There's something for everyone! Paddleboard or Kayak (provided) the beautiful canal to either lake. Enjoy your morning coffee or evening cocktail in nature on the dock. Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, they also offer sunset cruises and water taxi to Eaton's Beach restaurant right from our dock!

4.88 out of 5 average rating, 218 reviews

A modern living space is illuminated by soft sunlight streaming through large windows. The wooden flooring creates a warm ambiance, while a sleek sectional couch and decorative partition subtly define the area. A potted plant adds a touch of greenery to the environment.

Home in Summerfield

Modern Lake Weir House

Best sunset on Lake Weir! Lake front with private sand beach we are located on Sunset Harbor on Lake Weir. Plenty of dock space and beach space for several boats. House is on Bird Island and setup for entertaining friends and family. House was completely remodeled in 2018 with a modern contemporary design featuring 4 bedrooms, 2 bathrooms. One of the rooms is a movie theater with a 100” big screen that has a futon sofa. Can take the boat to Eaton’s Beach or Gator Joes just across the lake!

A single-story home is showcased with a light exterior and an attached two-car garage. Neat landscaping featuring low-maintenance gravel and diverse shrubs surrounds the entrance. A clear blue sky and a few palm trees contribute to the inviting atmosphere of the property.

4.89 out of 5 average rating, 118 reviews

Walk to Sumter w/cart - Beautiful Courtyard Villa

We love this home because the location is FANTASTIC! It's under a mile to Sumter Landing (walking distance for us :)). Also, new floors, paint, etc! The living room furniture is extremely comfortable! The kitchen has everything you need. The beds are comfortable and there is a tv in every room. (The second bedroom but needs your own Roku or Firestick!) There is a cart included which is the best way to see The Villages. We know you will love it here! Let us know if you have any questions.

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.

4.96 out of 5 average rating, 195 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.

4.95 out of 5 average rating, 99 reviews

Cabin in Dunnellon

The Owl A-Frame Retreat/ with hot tub

Escape to The Owl A-Frame a private cabin designed for special occasions. Here you won’t have any neighbors around just the peaceful sounds of birds and the magical sight of owls. Surrounded by impressively trees far away from city noise and distractions. This is the perfect place to relax and reconnect. Soak in the hot tub while listening to nature. If you’re looking for a peaceful family getaway, a nature escape, or a place to create unforgettable memories The Owl A-Frame offers it all.

4.95 out of 5 average rating, 228 reviews

A spacious wooden dock extends over the calm waters, surrounded by lush greenery. Several people are seated, enjoying a meal together. Lawn chairs are arranged comfortably, with trees reflecting off the clear surface of the water nearby, creating a serene atmosphere.

Home in Weirsdale

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.

Superhost

A custom home is framed by lush greenery and mature trees. The landscaped yard features a manicured lawn, and the house showcases a welcoming façade with multiple windows, allowing natural light to enhance its inviting presence.

Home in Summerfield

A+ Privacy | Hot Tub | BBQ + Dining | Family +Pets

Custom home with private garden, hot tub, outdoor dining & screened front porch. ★ "Beauituful home inside and out! I absolutely love the landscaping." ☞ Patio w/ alfresco dining + BBQ ☞ Backyard w/ private garden + hot tub ☞ Fully equipped + stocked kitchen ☞ Indoor jetted spa bathtub ☞ Card table + air hockey ☞ Multiple smart TVs (4) ☞ Indoor gas fireplace ☞ Pet friendly 11 mins → The Villages (cafes, dining, shopping) 12 mins → Eaton's Beach (swim + live music)

4.85 out of 5 average rating, 101 reviews

5.0 out of 5 average rating, 265 reviews

Guest house in Lady Lake

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.

An enclosed patio features a heated saltwater pool, accentuated by stone tile and decorative mosaic. Nearby seating options are visible, including a lounge chair under a shaded canopy. Lush greenery surrounds the area, providing a sense of privacy and tranquility.