Family-friendly vacation rentals in Wellington

Wellington Guest Suite

Wellington guest suite for the winter horse show season. Private entrance and it's separate from the rest of the home. Shared driveway parking. Quiet neighborhood. Close to restaurants, grocery stores, mall, show jumping, dressage, and polo attractions for your convenience. Rental to one/two person(s)only. No smoking. Small pets only. King size bed, full bath, walk-in closet, sofa, dinette table, TV, (Wifi access), kitchenette with fridge, microwave, toaster and coffee maker. No washer & dryer

Indoor spaces · Kitchen · Long stay

Wellington Pool Retreat | 4BR/2.5BA

Welcome to Wellington Pool Retreat! 🏡☀️ This spacious 2,500 sq. ft. home in the desirable Wiltshire Village community features 4 bedrooms, 2.5 bathrooms, and a private heated pool. Enjoy the fully screened patio with a new outdoor kitchenette, 4K TV, lounge seating, and updated lighting—perfect for relaxing or entertaining. Backing to a large tree-lined green space, the home offers exceptional privacy while being conveniently located near shopping, dining, and Wellington attractions. 🌴🏊‍♂️✨

Family · Indoor spaces · Quiet

Paradise Pool Cottage in Wellington/WPB/Polo

Beautifully appointed resort style 2 bed, 1 bath cottage. Located 5 minutes away from the Equestrian and Polo Grounds and 20 minutes from stunning South Florida beaches. This boutique style spa home is perfect for a laid back vacation style trip to the WEF, a perfect base for exploring the Palm Beaches, an overnight concert trip to the Amphitheater and Sunfest. The tropical patio, heated saltwater pool and hot tub are ideal for relaxing around, with sun loungers, outdoor eating area and grill.

Family · Kitchen · Laundry

*5 STAR* Family Friendly 3 Bed Home w. Heated Pool

Our Wellington home is perfect for equestrians, families or those just looking for home away from home while in the area. We don't use the word home lightly - this is our residence when we are in Wellington, so no detail has been overlooked. Complete with comfortable floor plan with renovated kitchen & baths. Details include hi-speed WIFI, smart-home, new washer/dryer and screened patio area w. kid fence - perfect for relaxing poolside, both day & night. Amenities for ALL kid ages from 0 - 18!

Indoor spaces · Family · Accuracy

Cozy Home with Pool & Spa (Heated) in Wellington

This home is set up to provide all the comforts you need. This beautiful property is located minutes from the equestrian centers. There is a screened in pool area allowing you to enjoy the pool without needing to worry about any Florida bugs. The spa is perfect for relaxing. All the bedrooms are comfy, and the master provides comfort and plenty of space for quiet time if needed. There are also two living room areas, and plenty of seating set up so memories and family time will be easy to have

Kitchen · Family · Value

Saddle Up in Style

Escape to this stylish Wellington retreat in the heart of horse country—minutes from stables, shows, and races. Enjoy a chef’s kitchen, and spacious outdoor dining perfect for family meals. Unwind with ping pong, board games, or a cozy movie night. For those working on vacation (seriously, why?), there’s a desk and monitor ready to go. We won’t judge—just don’t forget to hit the pool after those emails. Whether you're here for the equestrian scene or just to relax, this home has it all.

Indoor spaces · Kitchen · Beach

1 Paradize for equestrian lovers Sugar Pond Manor

This is a warm and guest friendly house . We did our best for you to feel at home and enjoy your stay.In sunshine state of Florida you can enjoy our private pool and BBQ. Is great location for friends or families. In only 10-15 min you can visit zoo,water parks, great restaurants, shopping malls,golf clubs,opera or drama theatre. This is could be a romantic get a way or family trip there a lot of fun activities for any purpose. We love staying in our house and we hope you will too.

Indoor spaces · Family · Quiet

Alluring Luxury Oasis: Modern Comfort & Relaxation

Escape to your private haven in a prime location in the heart of Wellington in at Villa Azalea, a stunning villa nestled within the peaceful Sugar Pond Manor community. This freshly designed retreat is the perfect home base for exploring Wellington's equestrian scene, vibrant culture, and natural beauty. Experience the finer things as you relax in a stylish space with a fully equipped kitchen, comfortable living area, and in-unit washer/dryer for ultimate convenience.

Family · Indoor spaces · TV

Elegant & Glamorous way private pool with heater

Welcome to this spacious and stylish home designed for guests who enjoy comfort, luxury, and beautiful surroundings. This large property features a sophisticated blend of modern elegance and glamorous details, creating the perfect atmosphere for unforgettable family vacations. open living spaces with high-end décor, comfortable seating, and a warm, inviting ambiance. The home offers multiple bedrooms, ideal for large families or groups who want to relax together

Indoor spaces · Family · Accuracy

Entire Home With Luxury Pool and Heated Spa

Escape to a luxury 3-bed, 2-bath South Florida oasis in the heart of Wellington. This private home comfortably fits 6 guests and features a large swimming pool, hot tub, two living rooms, and a fully equipped kitchen. Perfectly located, you can walk to local shops, diverse restaurants, and a movie theater. Enjoy the ultimate relaxing getaway with exclusive access to your own private paradise, complete with a BBQ grill and a two-car garage for your convenience.

Kitchen · Family · Accuracy

Newly Renovated House with Luxury Pool

Villa Matilda is a brand-new luxury modern 2-bedroom, 1-bath home perfect for couples, families, or equestrian guests. Enjoy a bright open living space, fully equipped kitchen, cozy bedrooms, and a sparkling private pool. Relax in the serene backyard, sip your morning coffee, or take advantage of nearby riding trails and stables. Stylish, comfortable, and private — the perfect Florida retreat for sun, relaxation, and adventure!

Family · Kitchen · Pool

Secluded Guest House | Upscale Wellington

Escape to your own private retreat in one of Wellington's most beautiful and sought-after neighborhoods. This secluded guest house is the perfect base whether you're here for a beach day, exploring South Florida, or simply unwinding in a quiet, upscale setting. Enjoy complete privacy, stylish comfort, and everything you need for a relaxing stay — just minutes from the beach, golf, shopping, and dining.

Indoor spaces · Kitchen · Decor