Pet-friendly holiday rentals in The Villages

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.

4.95 out of 5 average rating, 145 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

4.96 out of 5 average rating, 345 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.

A spacious living area is presented, featuring a light-colored sofa paired with white accent tables. A ceiling fan above enhances airflow, and modern kitchen appliances are visible in the background. Natural light floods the space, highlighting the hardwood flooring and simple decorative touches.

5 out of 5 average rating, 35 reviews

Bay Breeze Villa Free Golf Cart Close to Eastport

Welcome to Bay Breeze Villa, where modern comfort meets coastal charm. This brand-new 2-bedroom, 2-bath patio villa seamlessly blends style and functionality with sleek finishes and an inviting atmosphere perfect for relaxing or entertaining. Located in a vibrant community, close to top-rated restaurants, beautiful golf courses, and nightly entertainment. Embrace the relaxed yet active lifestyle you’ve been dreaming of – Bay Breeze Villa is the perfect place to call your home away from home.

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, 188 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.

5 out of 5 average rating, 26 reviews

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

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 .

5 out of 5 average rating, 9 reviews

Home in Fruitland Park

Amazing home in The Villages, FL

Enjoy your stay in one of America's most vibrant communities, The Villages, at this stylish and modern three-bedroom home in Pine Hills. This recently built house is the perfect home-away-from-home, with everything you'll need to relax and unwind after a busy day of adventure in Central Florida! Our home can accommodate up to eight guests. We have four beds and a sleeper sofa, up-to-date appliances, a screened lanai, grill and more! We also have a golf cart guests can use, free of charge!

5 out of 5 average rating, 34 reviews

Newest Hotspot in The Villages Eastport/Middleton”

Welcome to Eastport! The Villages’ most exciting new lifestyle destination — Eastport! Whether you're visiting for a weekend getaway or an extended stay, this beautifully furnished 2-bedroom, 2-bath Patio Villa w/golf cart puts you in the heart of everything The Villages has to offer — golf, pickleball, shopping, dining, entertainment, recreation, and serene nature. From the moment you arrive, you’ll see why Eastport is the new standard for luxury, leisure, and active adult living.

The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.

4.97 out of 5 average rating, 103 reviews

Fabulous Courtyard Villa close to Sumter Landing

This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.

A living area contains a light-colored leather couch and two armchairs, complemented by a wooden coffee table. Natural light enters through large windows adorned with light curtains, revealing a view of greenery outside. Soft, textured rugs cover the wooden flooring, enhancing the cozy atmosphere.

5 out of 5 average rating, 7 reviews

"Oasis"-Walk to Lake Sumter

You will feel welcomed to The Villages when you arrive to this ideally located peaceful courtyard Villa. Walking distance to Lake Sumter Landing, where you will enjoy shopping, restaurants and nightly live entertainment in the square. Take a short stroll to the Virginia Trace pool or hop in the included gas golf cart and enjoy a ride to anywhere you want to go in The Villages. This house is easily accessible to either Spanish Springs or Brownwood Squares.

4.99 out of 5 average rating, 169 reviews

Private 3/2, 2 Golf Carts, Pizza Oven, Game Table!

3-bedroom (sleeps 6), 2-bath home in The Villages with 2 golf carts! Screened & covered patio includes grill, pizza oven, fire table, outdoor seating, table and privacy - rare in The Villages! Access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in family room, all bedrooms & patio, fully equipped kitchen, gaming table & more! 10 minutes to Spanish Springs & Sumter Landing Town Squares.

5 out of 5 average rating, 58 reviews

The exterior of a villa is showcased at dusk, featuring a well-maintained landscape with palm trees and shrubs. A two-car driveway leads to a garage, with soft lighting illuminating the entrance. The sky reflects pink and purple hues overhead.

Villa in The Villages

Courtyard Villa | Golf Cart + Dog Friendly

Welcome to Palm Oasis Retreat, a dog-friendly courtyard villa in The Villages! Ideally located between Brownwood Paddock Square and Lake Sumter Landing, this charming home features 2 bedrooms, 2 baths, a private fenced courtyard, enclosed lanai, gas grill, and a complimentary 2-seater gas golf cart. Enjoy easy access to golf, dining, shopping, recreation centers, and nightly entertainment—all designed for a relaxing and memorable stay.

A screened lanai features comfortable seating and is positioned adjacent to a well-maintained backyard. A tree is situated in the grassy area, providing shade, while a concrete pathway leads to the entrance. A white fence encloses the yard, enhancing privacy.

4.92 out of 5 average rating, 153 reviews

Briar Meadow Villa - Dogs are welcome!

Dogs are welcome in this nicely furnished Courtyard Villa, with a fenced in backyard. Near Nancy Lopez Legacy Golf & Country Club, Mulberry Grove Rec Center, dog park, Publix, Walgreens, & The Club Health & Rehab Clinic. Easy access to pools, golf courses, dining, shopping & the squares at Spanish Springs & Sumter Landing. Includes gas Golf Cart*, Comcast cable TV, high speed WIFI, & Villages Daily Sun. *Subject to availability

Popular amenities for The Villages pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A serene view of a golf course at sunset, featuring a calm body of water reflecting vibrant orange and purple hues. A fountain can be seen gently spraying water in the foreground, with a silhouette of a large tree and distant homes framing the scene.

4.92 out of 5 average rating, 37 reviews

Mi Casa Es Su Casa at Hacienda

A wooden boardwalk winds gracefully along the edge of a tranquil waterway, surrounded by lush greenery and mature trees. Nearby, a pavilion stands, offering shaded views of the serene landscape, enhancing the outdoor experience.

4.95 out of 5 average rating, 22 reviews

StJohns is a great area for golf, hiking, Kayaking

An open-concept living space features a sectional sofa with soft cushions, accompanied by a stylish armchair. A ceiling fan hangs overhead, and natural light floods the area from large windows. A dining table for six and a kitchen with modern appliances are visible in the background.

4.9 out of 5 average rating, 84 reviews

Across pool, golf cart, modernized, private

A well-maintained exterior features a single-story villa with light grey siding and a simple gable roof. A gas cart is parked on the driveway, surrounded by neatly trimmed shrubs and gravel landscaping, adding to the property’s welcoming ambiance.

4.96 out of 5 average rating, 139 reviews

Lake Sumter 2/2 Villa FREE gas cart/Pet friendly

4.97 out of 5 average rating, 35 reviews

Home in Yalaha

Eden Escape Suite Lake Harris Florida

A single-story villa is depicted with a well-kept exterior, featuring a white picket fence surrounding the front yard. A spacious driveway leads to a two-car garage with a closed door. The sky is clear, showcasing a few fluffy clouds.

4.88 out of 5 average rating, 25 reviews

2/2 Villa 5 min from Lake Sumter Landing-pets

4.93 out of 5 average rating, 45 reviews

A patio villa in Deluna, The Villages w/ Golf Cart

4.92 out of 5 average rating, 13 reviews

2 min to Brownwood in Richmond!

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 145 reviews

An open-concept living area features natural light streaming through large windows with scenic views of the lake. Cozy seating arrangements include a comfortable sectional and accent chairs, complemented by a dining space and a well-equipped kitchen with modern appliances.

Home in Tavares

Lake Dora Dream-Waterfront/Pool

The kitchen features modern stainless steel appliances and a large island with seating for four. The quartz countertops complement the rich cabinetry and vibrant blue wall. Pendant lights provide illumination, enhancing the sleek design of the space.

5 out of 5 average rating, 22 reviews

Designer Home in The Villages, FL.

5 out of 5 average rating, 8 reviews

Heated Pool, Golf Cart, Life Stlye ID's

A spacious screened lanai features comfortable seating arranged around a glass-top table. Outdoor dining spaces with a large umbrella and views of the fenced yard and greenery are visible in the background, providing a serene setting for relaxation.

5 out of 5 average rating, 6 reviews

Huge & luxurious home w/view of preserves & fenced

A screened-in lanai features a heated pool with clear blue water, surrounded by a comfortable outdoor seating area. Two loungers and a table with chairs are visible, along with potted greenery enhancing the space. A view of the fenced yard and neighboring homes can be seen.

4.95 out of 5 average rating, 20 reviews

Family Tides 3 Richmond

An open-concept living area showcases a cozy seating arrangement with a leather sofa, complemented by a large dining table. The well-equipped kitchen features modern cabinetry and appliances. Sunlight filters through the windows, illuminating the space and creating a welcoming environment.

4.93 out of 5 average rating, 58 reviews

Village of Deluna at Marsh Bend 3bd 2bth

The image displays a bright, welcoming ambiance created by soft natural light filtering through sheer curtains. Beautiful yellow flowers in the foreground draw attention, emphasizing the inviting aesthetic. Decorative text presents key features of the Margarita House, including spaciousness and views of the backyard.

4.91 out of 5 average rating, 23 reviews

Vacation in luxury at Margarita House!

A single-story home is set against a bright sky with sun rays radiating. The front yard includes a white picket fence and a tropical palm, with gravel landscaping contrasting against the lush green lawn.

4.95 out of 5 average rating, 38 reviews

Pet Friendly in the Villages!

Private, pet-friendly home rentals

4.96 out of 5 average rating, 70 reviews

The exterior of a charming cottage is highlighted, featuring a welcoming front porch with a single chair. Light-colored siding contrasts with dark shutters, and a decorative wreath adorns the door. Surrounding open fields and a fenced yard enhance the rural setting.

Farm stay in Belleview

Farm Stay at The Cottage

The home's exterior is framed by well-maintained landscaping, featuring palm trees and a manicured lawn. A flagpole displays the American flag, adding a patriotic touch. A spacious driveway leads to the entrance, while a glassed-in porch is visible on the front.

4.95 out of 5 average rating, 57 reviews

Great location w/ golf cart! Lake Sumter-Brownwood

5 out of 5 average rating, 10 reviews

2 golf carts! 3/2 Courtyard Villa sleeps 6

Superhost

5 out of 5 average rating, 4 reviews

The Blue Door - The Villages! Plus Golf Cart/Bikes

4.91 out of 5 average rating, 89 reviews

A spacious hallway leads to a living area featuring a large window with natural light filtering through. A neutral color scheme is complemented by a decorative lamp and fresh flowers on a sideboard. Comfortable seating arrangements are seen in the inviting living space.

Villa in The Villages

3BR at 1198 Merryweather Way; just 4nt min; pet ok

Superhost

A winding driveway leads to a large Tudor style home, framed by tall trees and shrubs. Stone pillars with lanterns flank either side of the driveway, providing a welcoming entrance. The property is set on expansive land, surrounded by lush greenery.

4.83 out of 5 average rating, 12 reviews

Large Home on 10 acres

4.94 out of 5 average rating, 18 reviews

Perfect Location/Fenced In Backyard/Lanai/Dogs OK

A contemporary single-family home is showcased, featuring a light-colored exterior with neatly landscaped greenery in the front yard. A golf cart is parked on the driveway, alongside a two-car garage and welcoming entrance, under a clear blue sky.