Family-friendly vacation rentals in Wildwood

Heated Pool & Kayaking House in Lake Panasoffkee

Bring the whole family to this great place with lots of room for fun. Enjoy this stylish house very close to the lake. Create new memories while staying at this beautiful property and all its amenities such as an indoor pool with nature view. Designed play room with pool/hockey air table and so much fun. With lake access from the its yard and 5 minutes from all restaurants and entertainments at Lake Panasoffkee. This fully renovated house will make your trip a unique and unforgettable experience

Indoor spaces · Family · Check-in

Safari themed private addition with pool/hot tub.

This special Guest house addition is Central to everything in The Villages! Making it easy to plan your visit. In The Village of Osceola Hills @ Soaring Eagle Preserve. Just North of Rt 44. A short golf cart or car ride to Brownwood Square & Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Play over 50 golf courses at a minimal fee, & free rec centers! We have an easy 4 seater Golf-cart rental , & request free Guest passes!

Indoor spaces · Family · Getting around

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.

Family · Kitchen · Pool

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

Great getaway for a single, couple, or a family. Only an hour from the Disney Parks! By golf cart, you are only minutes from pools, rec. centers, golf courses and many dining options as well as the grocery store. The home includes a nice outdoor seating area. The "squares" provide FREE nightly entertainment. Golf cart included in price for getting around in The Villages. This get-away home is perfect for people looking to relax OR never be bored! It's always a great day at The Villages!

Family · Kitchen · Accuracy

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.

Kitchen · Family · Layout

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.

Kitchen · Indoor spaces · Nearby

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. It’s only 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 spaces · Kitchen · Hospitality

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!

Family · Indoor spaces · Checkout

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.

Family · Indoor spaces · Location

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.

Kitchen · Indoor spaces · Laundry

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.

Family · Indoor spaces · Check-in

Htd Pool & Attached Hot Tub. Rare corner propty

New heated pool with attached hot tub and waterfall! Located in the coveted Village of Richmond, experience a rare rental retreat with stunning 270° water views and total privacy near Brownwood Square—minutes from shopping, dining, and medical facilities. Enjoy a breathtaking bird estuary sanctuary while relaxing in the new heated pool with attached hot tub, open-concept living with elegant finishes, and a fenced backyard oasis.

Family · Kitchen · Amenities