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, 156 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 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.

5.0 out of 5 average rating, 42 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 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, 117 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.

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, 59 reviews

Golf cart included near Sumter and Brownwood

Enjoy The Villages lifestyle with an included gas golf cart and a convenient central location near two popular town squares. Cruise to Lake Sumter Landing in about 12 minutes or Brownwood Paddock Square in about 17 minutes by golf cart. SeaBreeze Recreation Center is just minutes away for swimming, pickleball and more. Back at home, relax in the glass-enclosed lanai or screened outdoor patio, fire up the gas grill, or simply enjoy the quiet neighborhood. One small dog under 25 lbs is 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.

4.88 out of 5 average rating, 60 reviews

Olivia's Oasis

Enjoy a peaceful retreat in this cozy, fenced home featuring 2 bedrooms, 2 bathrooms, a full kitchen, garage, living room, office space, and a lanai. Conveniently located close to Orlando's theme parks and beautiful beaches, plus all the amazing amenities The Villages has to offer: pools, golf, and more! Golf cart included. Whether you're looking to relax in a quiet area or explore nearby attractions, our home is perfect for a memorable stay. Book now for an unforgettable experience!

5.0 out of 5 average rating, 13 reviews

Luxury Villages Stay • Golf Cart • Near Brownwood

Welcome to your Villages retreat! Step into comfort and style in this beautifully decorated, designer home fully furnished with everything you need for a relaxing stay. From cozy bedding to modern furniture. Located in the sought-after Village of Osceola Hills, end of Moyer Blvd just south of Route 44, this spacious 3-bedroom, 3-bathroom home (2021 sq. ft.) features a 2-car garage and comes with a golf cart. You're just minutes away from Brownwood (3 miles) and Sawgrass Grove (2 miles).

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.

5.0 out of 5 average rating, 61 reviews

Pirates & Parrots - The Villages - Golf Cart &Pool

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!!

4.99 out of 5 average rating, 176 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.

5.0 out of 5 average rating, 6 reviews

Htd Pool & Attached Hot Tub. Rare corner propty

New heated pool with attached hot tub and waterfall! Located in the coveted Village of Richmond, experience a rare rental retreat with stunning 270° water views and total privacy near Brownwood Square—minutes from shopping, dining, and medical facilities. Enjoy a breathtaking bird estuary sanctuary while relaxing in the new heated pool with attached hot tub, open-concept living with elegant finishes, and a fenced backyard oasis.

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.

4.94 out of 5 average rating, 162 reviews

Villages-Private Heated Pool-Central Location

Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses

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, 119 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!

4.97 out of 5 average rating, 106 reviews

Updated Villages Getaway Sumter Landing&Golf Cart

🌴 Updated 2BR/2BA Villa Near Sumter Landing! Enjoy a freshly painted villa in the Village of Largo with a newly remodeled master bath, king & queen beds, new stainless-steel appliances, and a fully equipped gourmet kitchen. Relax on the lanai, fire up the grill, or enjoy TVs throughout the villa. Community pools are just 1½ blocks away, and your golf cart is included for exploring The Villages! .

Popular amenities for The Villages pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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

5.0 out of 5 average rating, 42 reviews

Newest Hotspot in The Villages Eastport/Middleton”

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.

4.98 out of 5 average rating, 40 reviews

Lovely Largo Lantana

5.0 out of 5 average rating, 14 reviews

Seashell Villa~Pet Friendly~Golf Cart

5.0 out of 5 average rating, 10 reviews

Sawgrass & Eastport Town Square Golf Community

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.

5.0 out of 5 average rating, 15 reviews

Beautiful 2 Bedroom Home in The Villages!

Superhost

A single-story house is set in a well-kept yard with lush greenery and landscaped flower beds. The structure features large windows, allowingnatural light into the interior. A clear blue sky with scattered clouds is visible above, enhancing the sense of openness.

4.8 out of 5 average rating, 10 reviews

Luxurious Home in The Villages

5.0 out of 5 average rating, 7 reviews

Heated Pool + GOLF CART - Village of Santiago!

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 105 reviews

King Bed, Golf Cart, Small Dogs & Water Filter!

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, 157 reviews

Briar Meadow Villa - Dogs are welcome!

4.98 out of 5 average rating, 163 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

Superhost

A modern living area features a spacious sectional sofa in gray, complemented by a wooden coffee table. The open floor plan connects to a kitchen with stainless steel appliances and seating for four at the bar. Decorative wall elements add interest to the neutral walls.

Home in Lake Panasoffkee

Heated Pool & Kayaking House in Lake Panasoffkee

4.85 out of 5 average rating, 117 reviews

5.0 out of 5 average rating, 30 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

A screened-in patio features a refreshing private pool surrounded by lush landscaping. Two chaise lounges are positioned beside the water, while a float rests in the pool. A fountain adds a tranquil element to the relaxing outdoor space.

4.97 out of 5 average rating, 97 reviews

Casa Santin Luxury in The Villages w/Private Pool

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.

4.96 out of 5 average rating, 23 reviews

StJohns is a great area for golf, hiking, Kayaking

5.0 out of 5 average rating, 13 reviews

The Creative Cottage! Premium Amenities!

Private, pet-friendly home rentals

A golf cart in a vibrant green color is parked outside a garage with a door adorned by multiple windows. The home features beige siding, and a lush green lawn is visible, complemented by a white picket fence in the background.

4.97 out of 5 average rating, 89 reviews

Melody Lane's Crafting Getaway - Cricut Included

A patio area features a round table surrounded by six chairs, positioned beneath a vibrant red umbrella. Lush greenery and colorful flowers line the edges, while a decorative fountain adds a touch of elegance. The villa's exterior is well-kept, with a clear blue sky overhead.

4.95 out of 5 average rating, 22 reviews

North Villages Patio Villa

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, 90 reviews

3BR at 1198 Merryweather Way; pet ok; walk to sq

The exterior of a modern house is showcased, featuring a light-colored façade and a well-maintained front yard. A driveway leads to a spacious garage, while landscaped greenery and a small tree add to the inviting appearance.

5.0 out of 5 average rating, 8 reviews

Lovely new home at The Villages

4.95 out of 5 average rating, 19 reviews

Perfect Location/Fenced In Backyard/Lanai/Dogs OK

The exterior of a single-story home is presented, featuring a welcoming entrance with landscaping that includes shrubs and small plants. A two-car garage is visible on the right side, and the smooth driveway leads up to the front door. Rooflines are in neutral tones under a clear sky.

5.0 out of 5 average rating, 19 reviews

Bright & Modern Sunshine Villa

4.97 out of 5 average rating, 78 reviews

Home in Lady Lake

The Promise Land~10 beds~New

A comfortable living area is presented with a neutral-toned sofa and decorative pillows. Natural light streams through large windows. A fan hangs from the ceiling, and a small dining table with chairs is positioned by the sliding doors leading to the outdoor space with views of the golf course.