Pet-friendly holiday rentals in Wildwood

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, 144 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

4.97 out of 5 average rating, 204 reviews

Cottage in Coleman

Romantic Escape on Peaceful Mini Farm

Escape to a peaceful private farm cottage just minutes from Villages. Enjoy a romantic, cozy retreat with a private fenced courtyard, mini farm charm, and thoughtful comforts throughout. Pets are welcome with no surprise fees. Easy self check-in and simple checkout make your stay stress-free. Close to Brownwood, dining, shopping, and I-75. Extra parking may be available for boats, trailers, or larger vehicles with advance notice. Traveling with family or friends? Ask about nearby sister rentals.

4.96 out of 5 average rating, 344 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 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, 133 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, 32 reviews

Newest Hotspot in The Villages Eastport/Middleton”

Welcome to Eastport! The Villages’ most exciting new lifestyle destination — Eastport! Whether you're visiting for a weekend getaway or an extended stay, this beautifully furnished 2-bedroom, 2-bath Patio Villa w/golf cart puts you in the heart of everything The Villages has to offer — golf, pickleball, shopping, dining, entertainment, recreation, and serene nature. From the moment you arrive, you’ll see why Eastport is the new standard for luxury, leisure, and active adult living.

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, 103 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, 144 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

Luxurious lakefront home on Lake Dora - 8 minutes to downtown Mount Dora and Tavares. Enjoy your vacation in this newly renovated pool home (Pool Not Heated) on Lake Dora and the Harris chain of Lakes. Bring your boat or rent one nearby to explore the area by water and cruise the Dora Canal to Lake Eustis. Included is a guest apartment with private entrance totaling 4 bedrooms and 4 full baths. Just a half mile to the Tavares Pavilion and dining in downtown Tavares.

4.96 out of 5 average rating, 136 reviews

A screened porch offers a view of the water and surrounding landscape, with seating options including a red leather chair and a light-colored sofa. Natural light fills the space, enhancing the connection with the outdoors.

Cottage in Inverness

Serendipity Lake private dock, canoes & kayaks

FL is in a drought, water levels are 8ft + lower than normal. You can still enjoy fishing and kayaking on our direct waterway. Watch the sunrise and sunset over the water on a private dock. This is a place you will want to come back to time and time again. We do provide kayaks and canoes to enjoy the lakes. Plenty of room for outdoor games and activities. Pet friendly. Just a short drive to downtown Inverness and 30 minutes to Crystal River. Simply perfect!

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, 153 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

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.

4.97 out of 5 average rating, 119 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, 122 reviews

The living room features comfortable furnishings arranged around a spacious coffee table. A large wall-mounted TV is visible, and natural light streams through sliding doors that open to the outdoor space. Dark accent walls add a touch of modern style.

Home in Ocala

Embers Place | Modern! | Private! | Arcade! | New!

🏡 Charming 4-Bedroom Retreat in Ocala, FL – Ideal for Families, a Couples Getaway 💑 & Groups 👯‍♀️! Welcome to our new, beautifully appointed home ✨ located in the heart of Ocala, Florida 🌴. This spacious 4-bedroom, 2-bathroom retreat offers the perfect blend of comfort 🛋️, luxury & convenience, close to I-175, making it an ideal getaway for anyone seeking a peaceful escape!

Popular amenities for Wildwood pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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, 22 reviews

Designer Home in The Villages, FL.

4.99 out of 5 average rating, 132 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 Fishing Firepit

An open-concept living area showcases a cozy seating arrangement with a leather sofa, complemented by a large dining table. The well-equipped kitchen features modern cabinetry and appliances. Sunlight filters through the windows, illuminating the space and creating a welcoming environment.

4.93 out of 5 average rating, 58 reviews

Village of Deluna at Marsh Bend 3bd 2bth

4.86 out of 5 average rating, 35 reviews

Home in Coleman

Peaceful Country Retreat Near The Villages

Superhost

A winding driveway leads to a large Tudor style home, framed by tall trees and shrubs. Stone pillars with lanterns flank either side of the driveway, providing a welcoming entrance. The property is set on expansive land, surrounded by lush greenery.

4.83 out of 5 average rating, 12 reviews

Large Home on 10 acres

5 out of 5 average rating, 12 reviews

Luxury Villages Stay • Golf Cart • Near Brownwood

A charming golf cart is parked on a concrete driveway, featuring a sleek design with a black canopy. The surrounding area is landscaped with greenery and flowers, complementing the residential home and two-car garage visible in the background.

5 out of 5 average rating, 13 reviews

Willie’s Place w/Golf Cart, Hot Tub & Dog Friendly

A modern kitchen is shown, featuring a large island with seating for four. Sleek stainless-steel appliances are complemented by light grey cabinetry. A decorative backsplash adds visual interest, while a spacious dining table is visible in the background, alongside framed coastal artwork on the walls.

5 out of 5 average rating, 8 reviews

Centrally Located Gem w/ Cart

Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 162 reviews

The exterior of a single-story house is illuminated by warm lighting at night. The structure features a central circular window and flanked by palm trees. Lush greenery and gravel landscaping surround the home, offering a welcoming presence against the darkened sky.

Home in Ocala

Relax in Ocala Fl

4.96 out of 5 average rating, 158 reviews

A collage showcasing various aspects of the Moto Ranch. The center features a bright living area with high ceilings. Surrounding images display outdoor activities, including ATV riding, kayaking, cycling, and horseback riding, set amidst lush green landscapes.

Home in Brooksville

Fuel Your Passion, Epic Moto Ranch Factory Ride

4.91 out of 5 average rating, 105 reviews

A large outdoor pool is surrounded by lush greenery and tall trees, providing a serene environment for relaxation. Clear blue water reflects the sky, and steps lead into the shallow end. A poolside chair is positioned nearby for convenient seating.

Home in Ocala

Ocala Oasis 4BR w/Pool/Cabana/Game Room/Mini Golf

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

4.97 out of 5 average rating, 70 reviews

Home in Lady Lake

The Promise Land~10 beds~New

5 out of 5 average rating, 26 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

The front view of a single-story home showcases a well-maintained exterior with a large driveway and a two-car garage. Flower beds flank the entrance, adding greenery to the façade. A warm evening sky transitions into shades of pink and orange above, enhancing the welcoming appearance.

4.81 out of 5 average rating, 81 reviews

Lovely Private 3 Bed/2 Bath Home in Paradise!

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, 21 reviews

Charming Villages Retreat

Private, pet-friendly home rentals

Superhost

4.69 out of 5 average rating, 49 reviews

Cheerful 3 bedroom house with office, free parking

5 out of 5 average rating, 17 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

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, 41 reviews

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

5 out of 5 average rating, 241 reviews

Guest house in Lady Lake

Cute & Cozy Tiny Guesthouse

5 out of 5 average rating, 27 reviews

Two goats are seen in a lush green field, one featuring a predominantly black coat with white markings, while the other is white with black patches. The surrounding grass is tall, contributing to the farm setting.

Ranch in Wildwood

Owl Cove Ranch Sunset Barn Apartment

A single-story home is featured with beige siding and green shutters, set against a partly cloudy blue sky. A covered porch leads to the front door, with neatly trimmed bushes and a manicured lawn surrounding the entrance. A concrete driveway provides easy access.

5 out of 5 average rating, 14 reviews

2/2 Villa in St. Catherine

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.

4.96 out of 5 average rating, 45 reviews

Delightful 2 bed/2 bath villa!

The exterior of a single-story home is shown, featuring a contemporary design with a two-car garage and a well-maintained lawn. The driveway is clear, and landscaping includes small shrubs and green grass leading to the front entrance under a covered porch.