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.

4.96 out of 5 average rating, 140 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

A golf cart is parked beside a modern villa, positioned on a pebbled driveway. A white picket fence outlines the property, and a garage door stands closed in the background. Clear blue skies provide a bright ambiance.

4.83 out of 5 average rating, 18 reviews

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

2 bed/2 Bath Villa,Pet fee $50,Golf Cart included,screened lanai, large patio & grill. Nicely decorated, meticulously maintained. Perfectly centrally located 5 minutes by Golf Cart to the main entertainment at Sumter Square & 20 min. from Brownwood Square. FREE Golf at Executive Courses, and many Champion courses to explore, Sport Pools, Family Pools & Adult Pools. Restaurants, shopping, nightly Live Musical Entertainment & so MUCH more! What are you waiting for? Book today and enjoy life.

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, 180 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.

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.

4.91 out of 5 average rating, 87 reviews

3BR at 1198 Merryweather Way; just 2nt min; pet ok

Large 3BR/2BA courtyard villa. Affordable luxury & 5-star reviews. PRIME LOCATION in CENTER of it all. Upscale furnishings. Walk to town square w/shops & restaurants. King & queen (new mattresses) & a full bed will sleep 6 comfortably. Fast WIFI; 2 Samsung Smart TVs (65" living room); 2 desks for laptop/at-home work. Private yard w/ patio chairs. Vinyl plank floor. No carpet. I also manage 2br home across street. Rent both & sleep 10; Rest of 2025=2nt min. Apr 2026=5nt min. Pet ok $40 fee.

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, 45 reviews

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

GREAT LOCATION!! A beautiful 2 bedroom 2 bath home with a saltwater pool and a hot tub. 77 inch TV with sound system, and 2 car garage/golf cart . Outdoor bar with big screen TV with seating area and a second seating area outside the bird cage. TV’s in both bedrooms. Great out door living! Minutes to everything via golf car: Brownwood 12 Sumter 16 Sawgrass 19. 4 champ golf and 7 exec golf courses 5-10. Publix, Walmart 5 minutes Golf Car 2022 Yamaha included! No smoking!!

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.

4.97 out of 5 average rating, 192 reviews

Cottage in Coleman

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.

4.99 out of 5 average rating, 160 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, 223 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.

5 out of 5 average rating, 5 reviews

Welcome to The Sanctuary~Pet Friendly w/Golf Cart

Enjoy a stylish experience at this brand new, centrally located upscale home we call The Sanctuary! Enjoy a brand-new spacious home with stylish furniture, comfortable beds, and an excellent location. Equipped with bikes, a golf cart and portable chairs for those nights at the square enjoying live entertainment, what more could you want? PLEASE NOTE: We require a signed rental agreement and a copy of your ID to finalize your reservation.

Two golf carts are parked on the driveway of a villa, one black and one red. Lush greenery, including palm trees, enhances the front yard, which is well-maintained and features a blend of grass and decorative plants. A clear blue sky and sunshine create a bright atmosphere.

4.97 out of 5 average rating, 117 reviews

Villa 2 Master Suites/2 Golf Carts Great Location

Beautifully Remodeled Private Courtyard Villa with two King Master Suites. Both bedrooms come with King Posturepedic Pillow Top Mattresses and Premium bedding, each with their own private bathroom & 32" HDTV's. LOCATED PERFECTLY in the De La Vista North neighborhood between Spanish Springs & Sumter Landing both offering dinning and shopping. The property comes with 2 Golf Carts making getting around SUPER easy & FUN!

A spacious living area features a comfortable sectional sofa with decorative cushions. A light-colored recliner is positioned nearby. Soft textures carpet the floor, complemented by a large rug. Natural light enters through multiple windows, creating a bright and open feel.

5 out of 5 average rating, 29 reviews

3/2 Courtyard Villa in The Village of Citrus Grove

Get comfortable and enjoy plenty of extra room at this spacious home. Large courtyard with a patio and lanai to soak in the Florida weather, open & spacious floor plan, TVs in both living room and master bedroom, and more! Only minutes away from Ezell recreation center and Homestead recreation center; close to pickleball, pools, classes, golfing, etc.

Popular amenities for The Villages pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A single-story villa is surrounded by a white picket fence and lush landscaping. The large covered patio features seating, offering a shaded area to relax. Nearby homes are visible, set amid a clear blue sky dotted with fluffy clouds.

4.97 out of 5 average rating, 35 reviews

You’ve Arrived! Stunning Home in the Villages!

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.

4.91 out of 5 average rating, 34 reviews

My House Is Your House at Hacienda

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, 77 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

A stylish living area features a combination of leather and upholstered seating, arranged around a circular coffee table. Natural light pours in through large windows, complemented by decorative plants. A geometric rug anchors the space, providing a cozy atmosphere for gatherings.

5 out of 5 average rating, 11 reviews

Sumter Landing Oasis / Golf Cart

A red golf cart is parked on a concrete driveway in front of a light-colored villa. The cart features a canopy with a patterned design and spacious seating for passengers. The attached garage is visible in the background, along with some landscaping.

5 out of 5 average rating, 15 reviews

Courtyard Villa in The Villages

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.

4.97 out of 5 average rating, 33 reviews

Pet Friendly in the Villages!

An open concept living and dining area is shown, featuring a modern dining table with seating for six. A comfortable sectional sofa faces a large flat-screen TV, while natural light enters through sliding glass doors leading to the enclosed patio. Decorative plants enhance the space.

5 out of 5 average rating, 13 reviews

Lynnhaven | 2 miles Sumter Square | walk to pool

Pet-friendly home rentals with a pool

4.94 out of 5 average rating, 18 reviews

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.

Home in Wildwood

StJohns is a great area for golf, hiking, Kayaking

4.97 out of 5 average rating, 125 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

4.95 out of 5 average rating, 147 reviews

A collage showcasing various aspects of the Moto Ranch. The center features a bright living area with high ceilings. Surrounding images display outdoor activities, including ATV riding, kayaking, cycling, and horseback riding, set amidst lush green landscapes.

Home in Brooksville

Fuel Your Passion, Epic Moto Ranch Factory Ride

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

The exterior of the house features a well-maintained driveway leading to a double garage. Lush landscaping with palm plants is visible, providing a welcoming entrance. The façade is painted in neutral tones, complemented by dark shutters and a simple porch lamp.

4.81 out of 5 average rating, 16 reviews

the villages Florida

4.98 out of 5 average rating, 174 reviews

The exterior of the property features a fenced yard with shaded trees and a front lawn leading to a single-story house. A pool area with protective mesh surrounds the heated pool, illuminated with vibrant LED lights in evening settings. Indoor spaces exhibit an open layout with natural light and comfortable seating.

Home in Minneola

Spacious Getaway ~ Heated LED Pool & Ping Pong

A single-story home is depicted in a well-kept neighborhood, featuring a manicured lawn with palm trees and shrubs. Two vehicles, including a golf cart, are parked in the driveway, while a cloudy blue sky provides a serene backdrop.

4.95 out of 5 average rating, 104 reviews

FREE Golf Cart + Fabulous Location + Classy Decor!

An aerial view of the villa showcases its well-maintained exterior with a pitched roof and a combination of light yellow and gray hues. A screened lanai can be seen, along with a spacious outdoor patio area. Lush greenery and colorful flower beds enhance the welcoming curb appeal.

5 out of 5 average rating, 11 reviews

Slice of Paradise! Great location in The Villages!

Private, pet-friendly home rentals

4.96 out of 5 average rating, 54 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.

4.96 out of 5 average rating, 53 reviews

Great location w/ golf cart! Lake Sumter-Brownwood

4.97 out of 5 average rating, 34 reviews

Home in Ocala

Upscale, Luxurious NEW HOME - 1.5 mi to WEC

5 out of 5 average rating, 9 reviews

2 golf carts! 3/2 Courtyard Villa sleeps 6

A single-story stucco home is showcased with a well-maintained front lawn, featuring a mix of shrubs and palm trees. A covered porch with rocking chairs is visible, enhancing the welcoming ambiance. The driveway leads to a garage with a glass door, contributing to the overall curb appeal.

4.9 out of 5 average rating, 20 reviews

Ensō House Relax in the heart of The Villages

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.

5 out of 5 average rating, 55 reviews

Palm Oasis Retreat - Dog Friendly w/golf cart

The exterior of the home is presented with a well-maintained lawn and landscaped garden, featuring palm trees and colorful shrubs. A golf cart is parked on the driveway, ready for convenient exploration of the community.

4.94 out of 5 average rating, 18 reviews

Spacious dog friendly home. King, Queen, & Sleeper

A single-story home is surrounded by lush green grass and palm trees. The driveway features smooth concrete, leading up to a spacious garage with modern glass doors. Soft clouds drift in a pastel sky, providing a serene backdrop to the property.