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, 150 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, 348 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 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, 113 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, 189 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 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, 96 reviews

Casa Santin Luxury in The Villages w/Private Pool

A refined Florida Luxury home designed for effortless indoor-outdoor living, Casa Santin blends modern coastal style with relaxed comfort—creating the perfect escape for your next getaway. Your Private Oasis. The highlight of Casa Santin is the stunning screened lanai and private pool—your own resort-style sanctuary. Start your mornings with coffee in the sunshine, spend afternoons poolside, and unwind in the evenings with a western sunset, a glass of wine under the soft glow of the lanai.

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, 54 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!!

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, 104 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.

4.96 out of 5 average rating, 99 reviews

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

Your NEW home includes a very comfortable KING BED and 4-Seater GOLF CART!! With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house NOVA 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!! 2 SMALL DOGS OK.

4.97 out of 5 average rating, 88 reviews

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.

Villa in The Villages

Melody Lane's Crafting Getaway - Cricut Included

Relax & watch TV on a 55” LG OLED. Complete with linens, kitchen equipment, high speed wifi, plenty of relaxing patio furniture outside and closed in lanai. Craft with the supplies and machines in the Dreambox. This Crafting Getaway is located in the gated Village of Alhambra just a short golf cart ride away from the popular Spanish Springs Town Square & Lake Sumter Landing which hosts shopping, restaurants, movie theaters, and free live entertainment nightly!

4.99 out of 5 average rating, 172 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, 250 reviews

Guesthouse 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.

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, 154 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

5 out of 5 average rating, 12 reviews

Seashell Villa~Pet Friendly~Golf Cart

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, 39 reviews

Bay Breeze Villa Free Golf Cart Close to Eastport

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 out of 5 average rating, 8 reviews

Lovely new home at The Villages

The front exterior of the home is displayed, featuring a well-maintained lawn and a paved driveway. The structure has a gabled roof with maroon and light gray siding. Two porch lights are mounted on either side of the entrance, and flowering shrubs enhance the landscaping.

5 out of 5 average rating, 16 reviews

Vacation home in The Villages

5 out of 5 average rating, 18 reviews

Eastport Emerald Escape 2BR Luxury in Well Point

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.

5 out of 5 average rating, 57 reviews

Moultrie Creek Retreat with Golf Cart

5 out of 5 average rating, 4 reviews

Heated Pool + GOLF CART - Village of Santiago!

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.

4.95 out of 5 average rating, 22 reviews

Charming Villages Retreat

Pet-friendly home rentals with a 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.

4.95 out of 5 average rating, 22 reviews

StJohns is a great area for golf, hiking, Kayaking

4.97 out of 5 average rating, 154 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, 23 reviews

Designer Home in The Villages, FL.

5 out of 5 average rating, 3 reviews

The 19th Hole Getaway*Pet Friendly w/Golf Cart

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

5 out of 5 average rating, 27 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

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, 14 reviews

Beautiful 2 Bedroom Home in The Villages!

5 out of 5 average rating, 39 reviews

Newest Hotspot in The Villages Eastport/Middleton”

Private, pet-friendly home 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 welcoming exterior of a single-story home is surrounded by well-maintained landscaping. A neatly trimmed lawn complements the vibrant plantings along the path. The garage door and front porch are illuminated, offering a sense of warmth as the sun sets in the background.

5 out of 5 average rating, 5 reviews

Newer home in Village of Hawkins

5 out of 5 average rating, 10 reviews

2 golf carts! 3/2 Courtyard Villa sleeps 6

5 out of 5 average rating, 6 reviews

Gorgeous Water View Villa near Lake Sumter Landing

4.95 out of 5 average rating, 20 reviews

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.

Villa in The Villages

North Villages Patio Villa

The exterior of the home features a well-maintained front yard with manicured shrubs and palm trees. A golf cart and bicycle are parked on the driveway, with a two-car garage visible. The atmosphere is bright under a partly cloudy sky.

5 out of 5 average rating, 27 reviews

Walking distance to Lake Sumter Landing!- Magnolia

4.91 out of 5 average rating, 90 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

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.