
Family-friendly vacation rentals in Wildwood
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Wildwood

Total vacation rentals
Explore 1,040 vacation rentals in Wildwood

Nightly prices starting at
Wildwood vacation rentals start at G$6,276 GYD per night before taxes and fees

Verified guest reviews
Over 15,810 verified reviews to help you choose

Pet-friendly vacation rentals
Find 430 rentals that welcome pets

Vacation rentals with a pool
420 properties feature pools

Rentals with dedicated workspaces
640 properties have a dedicated workspace

Wi-Fi availability
1,040 of Wildwood vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wildwood rentals

4.9 Average rating
Wildwood stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Wildwood
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.
KitchenFamilyAir conditioning

Get to the Choppa! One-of-a-kind 2/1 Helicopter!
Experience a truly UNIQUE Stay! “Chinook” is situated on a serene 5-acre compound inside the breathtaking Withlacoochee State Forest and the thrilling Croom Motorcycle Area, outside of Brooksville, FL. This unforgettable vacation experience is sure to take your adventure to new heights! Our one-of-a-kind accommodation, a REAL repurposed Chinook CH-47D helicopter, promises a stay like no other. This iconic “choppa” with the modern amenities of home, can not be found anywhere else in the world!
Indoor spacesFamilyParking

Majestic cabin on Fort Brook Farm
Get away from it all when you camp under the stars on our beautiful little farm. Our cabin is a bedroom with queen size bed and a sleeping loft that is a twin. Bring a sleeping bag for loft. This air conditioned and heated cabin has a little extra. There’s a sink, fridge, and a coffee maker with pods in the kitchenette. There’s a great fire pit that also is a grill. We have chairs and table to sit by your camp fire. The restroom and showers are separate. There is not a half bath in the cabin.
FamilyKitchenAccuracy

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.
KitchenFamilyCleanliness

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.
KitchenIndoor spacesLocation

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.
Indoor spacesKitchenDecor

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.
KitchenLocationPool

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.
KitchenIndoor spacesGetting around

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.
FamilyKitchenAccuracy

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.
Indoor spacesKitchenComfort

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
KitchenIndoor spacesBiking

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.
FamilyIndoor spacesHospitality
Popular amenities for Wildwood family-friendly rentals
Family-friendly home rentals with a hot tub

TreeHouse, Swings, HotTub, HeatedPool, ClearSpring
Indoor spacesFamilySleep quality

Spacious Bungalow with Pool and Courtyard
KitchenIndoor spacesComfort

Themed Disney Villa | Pool | Arcade | Resort ºoº
Indoor spacesKitchenLayout

Pool + Heated spa Family friendly King suite Oasis
FamilyIndoor spacesOutdoor spaces

Safari themed private addition with pool/hot tub.
Indoor spacesKitchenCleanliness

Luxury Villa! /Game Room/ Pool Heater
Indoor spacesFamilySleep quality

Modern Lake Weir House
KitchenFamilyCheckout

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)
KitchenFamilySolo travel
Family- and pet-friendly home rentals

Cozy Cottage, private back yard, and free coffee!
FamilyIndoor spacesLocation

Private Waterfront Cabin Retreat with Kayaking
Indoor spacesFamilyNearby

Inverness 2/2 Fenced Yard w/Hot Tub Availability
KitchenIndoor spacesNearby

Fabulous Courtyard Villa close to Sumter Landing
Indoor spacesKitchenWalkability

The Villages | Heated Pool | Walk to Sawgrass!
FamilyKitchenPets

Walk to Sumter w/cart - Beautiful Courtyard Villa
Indoor spacesKitchenCondition

Heated Pool + GOLF CART - Village of Santiago!
AccuracyHospitalityCleanliness

Pool and Spa Luxury Retreat
Indoor spacesKitchenAmenities
Family-friendly home rentals with a pool

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

2BR Mins to Pools & Eastport | Middleton | Patio
DecorCheck-inNearby

New, private pool getaway in The Villages, FL
Indoor spacesKitchenAir conditioning

Brownwood Square - Villages Home
Indoor spacesFamilyAmenities

Perfect "get-away" home for a couple or family!
FamilyIndoor spacesLayout

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

The Villages pool property with a 4-person cart
FamilyIndoor spacesGrill

New Luxury Home-Pool-Waterfront View-3 King Suites
Indoor spacesFamilyTV
When is the best time to visit Wildwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$37,446 GYD | G$43,304 GYD | G$41,839 GYD | G$30,543 GYD | G$24,894 GYD | G$24,894 GYD | G$21,966 GYD | G$21,129 GYD | G$21,756 GYD | G$24,476 GYD | G$28,032 GYD | G$30,752 GYD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
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- Walt Disney World Resort
- Weeki Wachee Springs
- Orange County Convention Center
- SeaWorld Orlando
- Disney Springs
- Universal's Volcano Bay
- Rainbow Springs State Park
- Epcot
- Camping World Stadium
- Kia Center
- Disney's Animal Kingdom Theme Park
- Discovery Cove
- Tinker Field
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Disney's Hollywood Studios
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- Aquatica
- Epperson Lagoon
- Island H2O Live!
- Weeki Wachee Springs State Park
- Ocala National Forest
- Blue Spring State Park





