House holiday rentals in Wildwood

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, 115 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.

LocationFamilyTV

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 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.

FamilyValueTV

An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.

4.98 out of 5 average rating, 112 reviews

New Luxury Home-Pool-Waterfront View-3 King Suites

Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

LocationFamilyOutdoor spaces

A spacious living area is highlighted by a large, L-shaped sectional sofa with patterned pillows, surrounded by two blue armchairs. A round wooden coffee table sits centrally on a decorative rug, while natural light flows through windows that offer a view of the outdoors.

4.99 out of 5 average rating, 124 reviews

VIEW-T-FUL! w/Golf cart

Stunning entry with one of a kind picturesque setting and unbeatable location all in one. This lanai was redesigned with no support columns to have this spectacular highly desirable panoramic golf front & water view. Sweeping view of Southern charm, cluster of mature oak trees with Spanish moss. The back of the home facing the morning sunshine lighting up the lanai and screen area for a fine morning of relaxation. Don't hesitate, this home has it all, golf cart too!

FamilyLocationNearby

4.96 out of 5 average rating, 102 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.

LocationFamilyPets

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.

5.0 out of 5 average rating, 109 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 four-seater golf cart is included. One minute to the Waterlily golf cart bridge and eight minutes to Brownwood Square. Or Edna’s on the Green is just a few minutes away.

FamilyLocationAmenities

5.0 out of 5 average rating, 20 reviews

Eastport Emerald Escape 2BR Luxury in Well Point

Escape to The Eastport Emerald 🌴, a luxurious 2-bed, 2-bath villa in The Villages' Village of Well Point. This bright, open-concept home is ideal for snowbirds, vacationers, and extended stays, featuring 1GB fiber Wi-Fi, a chef's kitchen with gas range, and a private screened lanai. Enjoy self check-in with smart lock 🔑, community pools 🏊, lake access, and waterfront walking paths. Just a golf cart ride ⛳️ to Eastport Square and Sawgrass Grove.

LocationConditionNearby

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.

FamilyLocationOutdoor spaces

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.

5.0 out of 5 average rating, 31 reviews

Private home in The Villages

Welcome to your perfect get-away in The Village of St. John’s. The cozy 3/2 villa is bright, fully equipped and comfortably furnished and includes guest passes. Enjoy the convenience of nearby shopping, dining and entertainment at Brownwood Paddock Square. Stroll on the walking trail which leads along Lake Okahumpka to the Recreation Center. Whether you’re here for excitement or relaxation, this is the perfect base for your stay in The Villages.

LocationFamilyKitchen

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.

4.96 out of 5 average rating, 158 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

ValueLocationCleanliness

5.0 out of 5 average rating, 199 reviews

A spacious living area features a brown leather sofa paired with a wooden coffee table and decorative rug. A ceiling fan hangs above, and a large wall art piece depicting tropical leaves adds a splash of color. The adjoining kitchen is visible in the background.

Home in Inverness

Lake Tsala Gardens Waterfront Home

Welcome to our Tsala Gardens Home centrally located in Inverness. There is plenty of outdoor space and decks with room to relax and enjoy. This property has direct access to multiple lakes prime for bass fishing. Bring your boat and launch from the private community boat ramp or public ramp and dock up at our dock house. We are located one mile from downtown Inverness and its shops, restaurants, parks, and bike trails.

FamilyLocationDecor

5.0 out of 5 average rating, 11 reviews

Stylish Villages Getaway

Welcome to your modern luxury escape in The Villages. Perfect for snowbirds, couples, or families, this brand-new home is designed for comfort and convenience. Enjoy high-end furnishings, elegant interiors, and access to resort-style community amenities. Make the most of your stay with a premium 6-passenger golf cart, electric bikes, and endless entertainment. Stay active, relax, and create unforgettable memories.

FamilyLocationIndoor spaces

Popular amenities for Wildwood house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior of a spacious single-story house is visible, featuring a light-colored facade and a greenery-laden yard. A palm tree is seen in the foreground, while the driveway leads towards a garage on the right side.

4.92 out of 5 average rating, 148 reviews

Entire 3 BR Home(Sleeps 8)+Hot Tub in The Villages

FamilyLocationBackyard

4.96 out of 5 average rating, 352 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

LocationValueComfort

A heated pool is enclosed within a screened patio, featuring gentle water features and surrounded by lush greenery. Two wooden adirondack chairs and a small side table are positioned nearby, inviting relaxation in this outdoor space.

4.9 out of 5 average rating, 20 reviews

The Villages | Heated Pool | Walk to Sawgrass!

ValueLocationAccess

A charming home exterior showcases a light blue facade and a white picket fence, surrounded by vibrant landscaping. A two-car garage is positioned prominently, with decorative plants adding interest. The clear blue sky provides a bright backdrop, accentuating the inviting appearance of the house.

4.97 out of 5 average rating, 38 reviews

Brownwood Square - Villages Home

FamilyLocationLong stay

A private outdoor area features a heated pool and spa, surrounded by screen enclosure. Comfortable seating is arranged beside the pool, complemented by an outdoor dining setup. The space is designed for relaxation with a stylish stone paver patio and clear blue skies above.

4.93 out of 5 average rating, 15 reviews

Pool and Spa Luxury Retreat

FamilyLocationIndoor spaces

4.89 out of 5 average rating, 28 reviews

Endless Love, Pool, and a Water View! Pool & Cart

LocationFamilyAccuracy

5.0 out of 5 average rating, 10 reviews

Spotless 3BR Home w/ Golf Cart, Near Brownwood Sq

FamilyLocationTV

A modern living area features a yellow leather sectional sofa and a round coffee table. A dining area with a dark wood table and chairs is visible, along with a large flat-screen TV. Natural light filters through the window coverings, creating a warm ambiance.

4.95 out of 5 average rating, 22 reviews

Peaceful Oasis in Fenney

LocationFamilyAccuracy

Weekly house rentals

A modern home with a welcoming facade features a dual garage and a front entrance illuminated by a stylish light fixture. Large windows reflect the evening light, while a manicured lawn with minimal landscaping is visible in the foreground.

5.0 out of 5 average rating, 43 reviews

3/2 Designer Home W/ Golf Cart

ValueFamilyQuiet

5.0 out of 5 average rating, 9 reviews

New Home! Wildwood Area

Sleep qualityHospitalityComfort

4.92 out of 5 average rating, 12 reviews

Uniquely decorated home with private backyard

LocationFamilyIndoor spaces

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, 40 reviews

Bay Breeze Villa Free Golf Cart Close to Eastport

LocationValueLong 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.

4.87 out of 5 average rating, 54 reviews

Olivia's Oasis

ValueFamilyOutdoor spaces

5.0 out of 5 average rating, 13 reviews

Luxury Villages Stay • Golf Cart • Near Brownwood

LocationFamilyCheckout

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.

4.93 out of 5 average rating, 70 reviews

Stunning Villa 2B/2B With Golf Cart

LocationFamilyTV

The welcoming living area features a spacious sectional sofa paired with a comfortable armchair. A natural wood coffee table is centered on an area rug, while a flat-screen TV is mounted on the wall. Large windows allow natural light to fill the space, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 29 reviews

Welcome to the Sawgrass/Eastport Area The Villages

LocationFamilyAmenities

Private 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.

5.0 out of 5 average rating, 24 reviews

Designer Home in The Villages, FL.

FamilyLocationAccuracy

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.

5.0 out of 5 average rating, 47 reviews

Opal Oasis in The Villages

ValueFamilyParking

The open concept living area features high ceilings and contemporary furnishings. A comfortable sofa with two recliners faces a glass coffee table, while two leather chairs flank it. A round dining table for four is nearby, accompanied by a stylish chandelier above.

5.0 out of 5 average rating, 35 reviews

Lovely 2BR/2BA golf cart home The Villages St Cath

FamilyLocationPets

A golf cart is parked on a driveway leading to a home. Tropical plants and palm trees create a lush exterior atmosphere. The garage door is visible on the right, with a sunny sky and scattered clouds overhead.

4.82 out of 5 average rating, 66 reviews

Holiday home in the villages.

LocationFamilyCondition

4.91 out of 5 average rating, 11 reviews

Pebble Beach, near Brownwood Paddock Square

LocationGetting aroundComfort

Superhost

5.0 out of 5 average rating, 3 reviews

Htd Pool & Attached Hot Tub. Rare corner propty

LocationFamilyCleanliness

5.0 out of 5 average rating, 42 reviews

Newest Hotspot in The Villages Eastport/Middleton”

LocationValueGetting around

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.