Holiday rentals in Wildwood

4.95 out of 5 average rating, 22 reviews

Entire Home with an Office in Fenney

Furnished for the ultimate in guest comfort, entertainment & working online. Accommodates maximum of 2 guests who plan to sleep in the same bed. Only 1 bed provided. Bright office with large desk, TV, printer Furnishings are modern & luxurious, making you feel right at home. Fast Internet & YouTube TV Fully stocked kitchen Coffee & tea is complimentary Filtered home water system Please NON-smokers ONLY welcome NO pets Not suited for children Fees reduced for 28+ days; ask for details

An aerial view showcases a spacious property surrounded by lush greenery. The home features a neat driveway and is complemented by several nearby buildings, including a recreation center with a pool. Sunlight highlights the rooftops and well-maintained lawns.

5 out of 5 average rating, 91 reviews

Pool and fun right out back

Bring the family to this beautiful place with lots of room for fun. With the Waterlily Rec Center right out back you can walk to the family pool in just a few steps. Pickle ball, exercise equipment, corn hole, bocce ball, shuffleboard and a walking/biking path is all right out the back door. A golf cart is included for golfing and access to the rest of The Villages. 1 minute to the Waterlily golf cart bridge and 8 minutes to Brownwood Square. Or Edna’s on the Green is just a few minutes away.

A modern Patio Villa is depicted in a well-maintained neighborhood, featuring a gray and white exterior with a slanted roof. A blue golf cart is parked on the driveway, surrounded by neatly trimmed grass and small shrubs.

4.98 out of 5 average rating, 42 reviews

Latitude Adjustment

Change your latitude in this beautiful two bedroom, two bathroom Patio Villa in The Villages. Located in the Village of Newell, this spacious and modern home has everything you need to make your stay relaxing and fun, including a golf cart! Enjoy a cup of coffee from the Keureg after your morning stroll on one of the nearby nature trails. Pools, pickleball and golf are all five minutes by golf cart, along with dining and entertainment at Sawgrass Grove and twelve minutes to the new Eastport!

5 out of 5 average rating, 18 reviews

By Eastport and near Middleton/Sawgrass with Cart

This new home includes a cart in the heart of Easport, the mecca of all the entertainment and rec centers in the Villages, and is close to Middleton and Sawgrass entertainment squares as well; yet it's far enough that it is a peaceful retreat. The nearby premier recreation center Saluki has a pinball machine, arcade, ping pong, shuffleboard, bocce and family pool. A separate adult only pool is close as well. Guest passes are free and included is a newer gas powered 2 seater golf cart.

An outdoor view of the home's exterior is presented, featuring a silver golf cart parked on a concrete driveway. The well-maintained front yard includes a white picket fence and landscaped areas with shrubs. A spacious garage is visible in the background under a clear blue sky.

4.92 out of 5 average rating, 61 reviews

Stunning Villa 2B/2B With Golf Cart

Make this stunning home your retirement Villager get away! Located in the Village of Newell home is minutes away from Sawgrass, swimming pools, pickleball, golf, and so much more. This home comes with a 2 seater golf cart and an outdoor grill perfect for any season. Live music is a nightly occurrence and only a 5 minute golf cart ride away. Enjoy the sunshine with biking and walking paths only seconds away from the front door! We would love to host your next Villages, FL vacation!

The exterior of a modern single-story home is showcased at twilight, featuring a neatly landscaped front yard with tropical plants. A cozy seating area is visible by the entrance, and a two-car garage complements the home’s facade under a colorful sunset sky.

4.75 out of 5 average rating, 8 reviews

King-Sized Comfort

Take a break and unwind at this peaceful oasis.Welcome to your serene getaway in The Villages! This spacious “Hideaway” in peaceful DeLuna offers 2 king beds, 2 baths, and easy access to pools, pickleball, tennis, and more. Explore over 130 miles of golf cart paths in this vibrant 55+ community featuring 700+ golf holes, 100+ pools, and endless clubs and activities. Just an hour from Orlando’s theme parks and near cruise ports, it’s the perfect mix of fun, comfort, and Florida sunshine!

A stylish villa exterior is presented with a gray facade and a welcoming porch area. A well-maintained lawn features a white picket fence and newly planted shrubs. A golf cart is parked on the driveway, ready for use, while the surroundings depict a tranquil neighborhood setting.

4.97 out of 5 average rating, 73 reviews

Newer Villa in The Villages near Brownwood

Kick back and relax in this calm, stylish new villa in the Villages. It is within walking or a 3 minute golf cart ride to Brownwood Town Center where there are dining, shopping and nightly music. It is also near Lake Okahumpka Recreation Center where you can fish or kayak. This area has beautiful nature trails for walking or biking with separate golf cart paths. There is a neighborhood pool and other amenities nearby. It also comes with a complementary golf cart for your convenience.

Place to stay in The Villages

An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.

5 out of 5 average rating, 112 reviews

Safari themed private addition with pool/hot tub.

This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

4.94 out of 5 average rating, 223 reviews

A wooden dock extends over calm waters, framed by lush greenery and moss-draped trees. The tranquil scene is complemented by a screened dockhouse nearby, providing a secluded spot for relaxation and enjoying the natural surroundings.

Cottage in Floral City

Waterfront Cottage 2BR 1B

This charming house is located on nearly an acre of woodland. Fish from the dock of the screen room on the canal or kayak to the nearby lake. Relax in the private backyard Jacuzzi. Bike on the nearby Withlacoochee Trail. There are 2 bedrooms plus living room sleeper sofa, and a lanai with a day bed. Fully furnished. Orlando theme parks are 1 1/2 hour away, Busch Gardens 1 hour. Close to Weeki Wachee, Homosassa and Crystal River for manatee viewing or scallop season.

4.97 out of 5 average rating, 184 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.

5 out of 5 average rating, 212 reviews

Guest house 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 single-story house features a white exterior with a gabled roof and a two-car garage. A white picket fence and manicured shrubs border the front yard, while a concrete driveway provides ample parking space. Clear blue skies are visible in the background.

4.97 out of 5 average rating, 87 reviews

New home in the new part of the villages.

Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.

Popular amenities for Wildwood holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Wildwood

4.88 out of 5 average rating, 26 reviews

A tranquil sunset reflects off the calm lake surface, displaying hues of pink and purple in the sky. Outdoor seating is provided on a deck, with a dining table set against the serene backdrop of the water and surrounding trees.

Home in Lady Lake

Lakeside Retreat

Superhost

A modern kitchen features white cabinetry and stainless-steel appliances, including a refrigerator and microwave. A central island with two bar stools provides additional seating. Exposed wooden beams enhance the ceiling, while a narrow hallway leads to a decorative feature wall.

Flat in Wildwood

4.83 out of 5 average rating, 6 reviews

Little Farm House

A single-story vacation home is presented with a light exterior and a neatly maintained front yard. A white picket fence encloses colorful landscaping, while a spacious driveway leads to a two-car garage. Clear skies enhance the inviting curb appeal of the property.

5 out of 5 average rating, 41 reviews

Opal Oasis in The Villages

A screened-in patio area showcases two hanging chairs with cozy cushioning, accompanied by a low coffee table. A lush green artificial lawn enhances the space, while a ceiling fan provides airflow. Beyond the screens, outdoor seating is visible under a shaded canopy.

5 out of 5 average rating, 38 reviews

Private Villa + Golf Car by Lake Sumter Square

Villa in The Villages

4.86 out of 5 average rating, 90 reviews

My Haven Is Heaven

4.86 out of 5 average rating, 74 reviews

Aerial view of the villa displays a well-maintained exterior with palm trees and landscaped shrubs. The driveway leads to a garage, and a circular pathway connects to a fenced yard, enhancing the tranquil outdoor space.

Villa in The Villages

AMAZING Location! Villa Near Lake Sumter Landing

A living room is showcased with two blue sofas facing a glass coffee table. Soft lighting is provided by two table lamps and a large TV is positioned on a dark wood console. Colorful wall art adds brightness to the space, complemented by a dining area in the background.

5 out of 5 average rating, 23 reviews

Private home in The Villages