Pet-friendly holiday rentals in The Villages

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, 164 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

PetsWalkabilityPool

4.96 out of 5 average rating, 353 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.

Outdoor spacesPetsFamily

4.99 out of 5 average rating, 145 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- Dock+Kayaks+SUP board

Welcome to your peaceful Getaway on the Water. Whether you or your group are visiting the Villages, or just need a peaceful getaway to recharge, this is the place!There's something for everyone! Paddleboard or Kayak (provided) the beautiful canal to either lake. Enjoy your morning coffee or evening cocktail in nature on the dock. Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, they also offer sunset cruises and water taxi to Eaton's Beach restaurant right from our dock!

PetsOutdoor spacesGetting around

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.

Outdoor spacesGetting aroundAccuracy

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, 116 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.

WalkabilityPetsHospitality

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, 192 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.

WalkabilityOutdoor spacesLayout

5.0 out of 5 average rating, 13 reviews

The Creative Cottage! Premium Amenities!

Welcome to "The Creative Cottage" in the Village of Lake Denham! But don't let the word "cottage" fool you!. Sleep up to 6 family and friends in this 3BR 3BA stunning private home w/built-in Pool and many extra special touches from an owner who was a former event planner with an eye for originality and details that'll make your stay wonderfully luxurious! NOTE: Please pass this listing by if you're looking for a party house! We love our neighbors and only want guests who will be respectful!

WalkabilityOutdoor spacesLong stay

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, 58 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!

WalkabilityOutdoor spacesCheckout

4.97 out of 5 average rating, 106 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.

PetsOutdoor spacesView

4.96 out of 5 average rating, 104 reviews

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

Your NEW home includes a very comfortable KING BED and 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.

WalkabilityPetsBiking

4.99 out of 5 average rating, 175 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.

PetsOutdoor spacesValue

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!

Outdoor spacesPetsParking

Popular amenities for The Villages pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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!

PetsOutdoor spacesDecor

5.0 out of 5 average rating, 13 reviews

Luxury Villages Stay • Golf Cart • Near Brownwood

Outdoor spacesWalkabilityAmenities

5.0 out of 5 average rating, 13 reviews

Seashell Villa~Pet Friendly~Golf Cart

ComfortLong stayAmenities

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

Great location w/ golf cart! Lake Sumter-Brownwood

WalkabilityOutdoor spacesHospitality

5.0 out of 5 average rating, 5 reviews

Heated Pool + GOLF CART - Village of Santiago!

AccuracyHospitalityCleanliness

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

PetsOutdoor spacesParking

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

CheckoutLocationIndoor spaces

5.0 out of 5 average rating, 21 reviews

Eastport Emerald Escape 2BR Luxury in Well Point

AmenitiesSleep qualityComfort

Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 160 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

PetsOutdoor spacesLocation

4.85 out of 5 average rating, 116 reviews

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

Outdoor spacesPetsBackyard

The exterior of the home is framed by lush palm trees and neatly landscaped flower beds. A pathway leads to the entrance, featuring a covered porch with welcoming lights. The manicured lawn offers a serene atmosphere, complemented by well-placed outdoor lighting.

4.79 out of 5 average rating, 135 reviews

The Brownwood Brassie 3BR 2 Bath w/ Golf Cart

WalkabilityPetsDecor

5.0 out of 5 average rating, 12 reviews

Home in Weirsdale

Hilltop Hideaway Lake Weir

CheckoutHospitalityIndoor spaces

4.96 out of 5 average rating, 23 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

Outdoor spacesGetting aroundPool

The patio area features a shimmering pool with built-in seating. Lounge chairs are arranged nearby under the shade of a large umbrella, with a spacious outdoor living area visible in the background. The protective screen enclosure offers a sense of privacy.

4.94 out of 5 average rating, 31 reviews

Brewed Awakening-3/2 w/ Private Pool and Golf Cart

PetsOutdoor spacesLong stay

4.91 out of 5 average rating, 47 reviews

A patio villa in Deluna, The Villages w/ Golf Cart

Outdoor spacesWalkabilityComfort

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!

Outdoor spacesWalkabilityNearby

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

WalkabilityPetsHospitality

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.

5.0 out of 5 average rating, 59 reviews

Moultrie Creek Retreat with Golf Cart

WalkabilityPetsNearby

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, 21 reviews

North Villages Patio Villa

Outdoor spacesAmenitiesLaundry

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

WalkabilityOutdoor spacesAccuracy

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.

4.93 out of 5 average rating, 44 reviews

Ideal location! 3/2 Stetson model w/4 man golfcart

PetsOutdoor spacesLocation

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, 63 reviews

Shangri-La Villa - Beautiful, Private & Central

WalkabilityOutdoor spacesDecor

5.0 out of 5 average rating, 18 reviews

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.

Home in Wildwood

Bright & Modern Sunshine Villa

WalkabilityPetsSleep quality

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.