Pet-friendly holiday rentals in The Villages

4.96 out of 5 average rating, 331 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, 158 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

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.

4.91 out of 5 average rating, 102 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, 178 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, 127 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

4.96 out of 5 average rating, 68 reviews

The exterior of the home showcases a light gray façade with a welcoming front porch. Lush green grass is framed by neatly arranged flower beds, while a flagpole displays the American flag. A paved driveway leads to the entrance.

Home in Wildwood

2/2 Villa in Citrus Grove - Rates Reduced!

*Redone in 2023* - Brand new furniture throughout - Freshly painted - Screened in Lanai 2 Bedroom, 2 Bath located in Citrus Grove in The Villages, FL Great Location! - Very close to Citrus Grove adult pool - Homestead recreation center with family pool 0.7mi - Ezell Recreation Center 1.1mi - Sawgrass Complex 1.3mi There are several amenities for you to enjoy in The Villages - restaurants, bars, nightly live entertainment, shopping, golf, pickleball, shuffleboard, and so much more!

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, 102 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, 179 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.

4.96 out of 5 average rating, 114 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

DUE TO CANCELLATION FEB & 1/2 MAR AVAILABLE! 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!

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

This home greets you with a driveway Pelican painting, amazing landscaping and a decorative glass entry door. Savanna shutters and comfortable furniture throughout the home. 12 minute golf cart ride to Lake Sumter and 17 minutes to Brownwood Square. Use the included gas golf cart to get there! Sea Breeze Rec Center with pool, pickleball, etc. is just a few minutes away. Grocery stores closeby. Quiet neighorhood. Dogs under 25 lbs allowed.

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

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 a single-story villa features a light grey façade with a one-car garage and a well-maintained front yard. A white picket fence surrounds the property, complemented by tidy landscaping and a concrete driveway leading to the garage.

4.94 out of 5 average rating, 34 reviews

Delightful 2 bed/2 bath villa!

Sit back and relax in this peaceful 2 bed/2 bath villa in the Village of Piedmont. Located 1 mile from Nancy Lopez Country Club as well as 2 Executive golf courses and a Recreation Center. Located 15 minutes from Spanish Springs and Sumter Landing Squares! Close to shopping and grocery store. Villa has a small back yard and golf cart is included.

Popular amenities for The Villages pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A charming home is set against a clear blue sky, featuring a brick-paved driveway leading to a two-car garage. Lush greenery surrounds the property, with neatly trimmed shrubs and trees framing the front entrance, offering welcoming curb appeal.

4.96 out of 5 average rating, 28 reviews

Lovely Largo Lantana

A single-story home with a well-maintained lawn features bushes and a large tree at the front. A black golf cart is parked on the paved driveway, which leads to the entrance of the house, framed by two front-facing windows.

5 out of 5 average rating, 7 reviews

Walking distance-Lake Sumter Landing-Serenity

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, 11 reviews

perfectly located Villages home

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, 12 reviews

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

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, 17 reviews

Spacious dog friendly home. King, Queen, & Sleeper

Superhost

4.8 out of 5 average rating, 10 reviews

Last Minute Deal in The Villages, Pets Welcome

A spacious living room features a large sectional sofa facing a mounted television. Natural light filters through sheer curtains, highlighting a decorative area rug. A round coffee table sits in the center, with a wooden console against the wall, adding functional charm to the space.

4.95 out of 5 average rating, 38 reviews

Olivia's Oasis

The exterior of a single-story home is showcased, featuring a well-maintained lawn and manicured shrubs. A two-car garage is visible, along with large windows that allow natural light to fill the interior. The sunset casts a warm glow over the property.

5 out of 5 average rating, 9 reviews

Centrally Located, 3 b/2 b Home with Golf Cart

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 39 reviews

A cozy living area features two gray sofas adorned with decorative blue and white throw pillows. A wooden coffee table with a colorful centerpiece sits atop a patterned rug. Natural light enters through sliding glass doors, enhancing the inviting ambiance.

Home in Lady Lake

Oasis in Heart of The Villages

4.94 out of 5 average rating, 17 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, 115 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

4.9 out of 5 average rating, 139 reviews

Guest house in Inverness

Tranquil guest home with beautiful salt water 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.

4.88 out of 5 average rating, 8 reviews

Spacious Home in The Villages

5 out of 5 average rating, 24 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

4.97 out of 5 average rating, 114 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

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, 32 reviews

Pet Friendly in the Villages!

Private, pet-friendly home rentals

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, 75 reviews

Across pool, golf cart, modernized, private

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.

4.93 out of 5 average rating, 54 reviews

Shangri-La Villa - Beautiful, Private & Central

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.

4.89 out of 5 average rating, 19 reviews

Ensō House Relax in the heart of The Villages

4.91 out of 5 average rating, 87 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 2nt min; pet ok

5 out of 5 average rating, 17 reviews

A two-story home features a light blue exterior with a white garage door. A staircase leads to a front balcony above, while the driveway is lined with greenery and decorative stones. Surrounding trees provide a natural backdrop, enhancing the home's outdoor appeal.

Flat in Wildwood

Balcony Oasis Home

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!

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, 22 reviews

Vacation in luxury at Margarita House!

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.