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, 135 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 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.

4.92 out of 5 average rating, 13 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.

4.96 out of 5 average rating, 326 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 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, 171 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 well-maintained home is visible, with a neatly landscaped driveway leading to a garage. An orange golf cart is parked prominently in front, surrounded by lush green grass and a manicured shrub nearby. A white picket fence adds charm to the yard.

4.98 out of 5 average rating, 120 reviews

Private 2/2 Villa w/ New 4 Seat Gas Golf Cart

Relaxing home in quiet neighborhood w/ private yard, screened porch - rare in The Villages! Roanoke Retreat is a beautifully remodeled 2 bed/2 bath home - only 15 minute golf cart ride to Spanish Springs, 20 minutes to Sumter Landing . Rental includes 4 seat gas golf cart w/ access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in every room, fully equipped kitchen, new BBQ grill. 55+ community but no age restriction to visit

5 out of 5 average rating, 23 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 .

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, 36 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!!

4.96 out of 5 average rating, 167 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.

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, 136 reviews

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

Super clean 2-bed/2-bath property in Buttonwood with free use of gas cart. Nicely furnished, with washer/dryer, smart tv and vaulted ceilings. This patio villa is in a highly desirable area within walking distance to the Fishhawk pool, rec center and many golf courses. Equal distance between Lake Sumter Landing & Brownwood squares. $89 pet fee. 4 person cart available at $50/day. 2 person cart is free. Return cart full please.

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!

Your NEW home includes a very comfortable KING BED. With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house WATER filtration system, you’ll have everything you need for a relaxing and enjoyable stay in The Villages. Find out why The Villages is the fastest growing and largest 55+ community in the WORLD, where visitors of all ages are welcome to play. The fun and sun is only the beginning!!

4.96 out of 5 average rating, 111 reviews

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.

Villa in The Villages

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!

4.96 out of 5 average rating, 103 reviews

A spacious living area features a large teal sectional sofa accented with decorative pillows. In the center, a round coffee table displays a floral design. Abundant natural light floods the room through wide windows, enhancing its relaxed atmosphere.

Villa in The Villages

3/2 Luxury Villa, Golf cart included! Near Sumter!

Enjoy this luxury private Villa in the heart of The Villages, Florida! This delightful 3-bedroom, 2-bathroom is your ticket to experiencing the vibrant lifestyle of a Villager. This Villa is a 0.7 mile walk or short golf cart ride to Sumter Square with beautiful boardwalk views along Lake Sumter, live music every day, the Old Mill Playhouse movie theater, and a variety of boutiques and restaurants.

Popular amenities for The Villages pet-friendly home rentals

Kitchen

Wi-Fi

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.

4.91 out of 5 average rating, 33 reviews

My House Is Your House at Hacienda

A comfortable living room features a light gray sofa set paired with a striped armchair. A coffee table sits center stage, surrounded by three decorative lamps. Large windows allow natural light to fill the space, with views of the private backyard and lush greenery.

4.92 out of 5 average rating, 13 reviews

Discounted 3/2, Recent lifestyle home w/golf cart

The entrance area of the villa is adorned with colorful flowering plants and palm trees. Two light blue Adirondack chairs sit invitingly on a paved surface, under a bright blue sky scattered with fluffy white clouds. The home's entrance features a covered porch with a wreath on the door.

4.94 out of 5 average rating, 47 reviews

Shangri-La Villa - Beautiful, Private & Central

4.99 out of 5 average rating, 107 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: Kayak, SUP, fish, relax!

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, 9 reviews

Sumter Landing Oasis / Golf Cart

4.95 out of 5 average rating, 287 reviews

The exterior of the house is presented at dusk, showcasing well-manicured grass and landscaping. Soft lighting highlights the entrance and garage. A welcoming front porch is visible, framed by trees in the background, creating a serene environment.

Home in Leesburg

Peace and Quiet

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.

4.9 out of 5 average rating, 21 reviews

Vacation in luxury at Margarita House!

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.

4.92 out of 5 average rating, 13 reviews

Spacious dog friendly home. King, Queen, & Sleeper

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 105 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 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.

4.77 out of 5 average rating, 13 reviews

the villages Florida

4.95 out of 5 average rating, 103 reviews

A charming single-story home is set on a lush green lawn, surrounded by trees and landscaping. A welcoming front porch features a swing and a bright blue door, adding a touch of color to the natural surroundings.

Home in Ocala

Ocala Oasis-3 Bedrooms and Heated Pool!

The exterior of a single-story home showcases a light purple facade, a neatly landscaped front yard with minimal foliage, and a paved driveway. A one-car garage with a door stands alongside a covered porch, inviting guests to enter the welcoming space.

4.86 out of 5 average rating, 7 reviews

Spacious Home in The Villages

5 out of 5 average rating, 48 reviews

A spacious ranch-style home is set within a large green lawn, featuring light-colored exterior walls and a brown roof. The front porch is accessible from the centrally located entrance, surrounded by a wooden fence and lush trees that provide a sense of seclusion.

Home in Lady Lake

Ranch Retreat~10 beds~New

An aerial view showcases a charming villa with a well-manicured lawn. The property features a spacious driveway, a screened lanai, and tasteful landscaping, including shrubs and palm trees. Nearby homes can be seen, contributing to a cohesive community layout under clear skies.

5 out of 5 average rating, 11 reviews

Patio Villa - Pet Friendly 2/2 Home (South of 44)

4.97 out of 5 average rating, 107 reviews

The exterior of a spacious two-story house is depicted, featuring a large driveway leading up to a double garage. Symmetrical windows are framed by neatly manicured landscaping, and a decorative entrance is highlighted by a welcoming wreath. Surrounding foliage adds a touch of greenery.

Home in Ocala

Spacious 6BR Pool Home in Ocala

Superhost

The exterior of the home presents a well-maintained façade with light-colored siding and a single-car garage. A white picket fence surrounds the front yard, featuring a landscaped area with tropical plants and a circular stone planter. A clear blue sky enhances the inviting atmosphere.

4.8 out of 5 average rating, 15 reviews

5 Min Cart to Eastport or Sawgrass - Central - 5*

Private, pet-friendly home 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.

4.96 out of 5 average rating, 28 reviews

You’ve Arrived! Stunning Home in the Villages!

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.

4.89 out of 5 average rating, 72 reviews

Across pool, golf cart, modernized, private

A single-story villa is presented with a light exterior and a charming front porch. The driveway leads to a two-car garage, while low-maintenance landscaping features a manicured lawn and hedges. A white picket fence borders the property, enhancing the welcoming feel of the home.

4.88 out of 5 average rating, 17 reviews

Amelia Villa-Pet Friendly 2 Bd-Great Location

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.

5 out of 5 average rating, 15 reviews

Ensō House Relax in the heart of The Villages

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.

5 out of 5 average rating, 10 reviews

perfectly located Villages home

Superhost

A modern living area showcases a light beige sectional couch with accent pillows. A ceiling fan is mounted above, and natural light floods the space from adjacent openings. The open kitchen features sleek cabinetry, a bar area with stools, and stainless-steel appliances.

4.84 out of 5 average rating, 86 reviews

Inspire Retire - The Newest Side of the VillageS

5 out of 5 average rating, 27 reviews

The open concept living area features high ceilings and contemporary furnishings. A comfortable sofa with two recliners faces a glass coffee table, while two leather chairs flank it. A round dining table for four is nearby, accompanied by a stylish chandelier above.

Home in Wildwood

Lovely 2BR/2BA golf cart home The Villages St Cath