Vacation rentals with a pool in Wellington

Guesthouse in Flamingo Park

A heated pool is surrounded by tall hedges and lush tropical plants, providing a sense of privacy. The pool features a tiled border and gentle curvature, while lounge chairs positioned nearby invite relaxation under clear blue skies.

4.97 out of 5 average rating, 176 reviews

Tropical Cabana with Pool in West Palm Beach

Location, amenities & layout are ideal for long term stays! The separate Cabana area is perfect for working on your laptop, fixing a bite to eat, reading a book or watching TV. The Cabana also opens onto a heated pool, half bath & private hot/cold outside rain shower under tropical plants and orchids. The guest bedroom has a California King bed, cable TV and opens onto the pool . The entire area is enclosed by tall ficus and tropical plants so you will feel totally secluded from the rest of th

Superhost

A pool area is framed by lush greenery, featuring two red lounge chairs beside the water. A bright red umbrella provides shade over part of the patio, where potted plants and vibrant flowers add color to the scene.

Guest suite in West Palm Beach

4.83 out of 5 average rating, 765 reviews

2 rooms/1 king bed/1 sofa bed/ kitchenette/pool

Our place is located in a lush green setting away from it all but the Village of Royal Palm Beach with stores, restaurants and amenities is only five minutes drive away. If you want to live it up head for downtown West Palm Beach and its endless beaches including famous Palm Beach Island or Wellington Polo Grounds all within easy reach. Situated in the heart of South Florida where the sun always shines and only a short trip away to Disney or The Keys Islands at the very southern tip of Florida.

4.92 out of 5 average rating, 26 reviews

A spacious sleeping area features a platform bed with a light-colored quilted coverlet and contrasting patterned pillows. Soft overhead lighting is provided by a modern chandelier. A refrigerator is visible in the background, and natural light enters from a nearby window.

Farm stay in Wellington

Lux Equestrian Studio

Escape to comfort in this newly renovated, Insta-worthy studio, nestled on a picturesque horse farm in the heart of Wellington— minutes from WEF. Perfect for equestrians, business travelers, or weekend getaways, this stylish space features luxury finishes, Wi-Fi, & pool access. Wake up to serene farm views, capture stunning photos, and enjoy a cup of coffee on the private patio. With top dining, shopping, and equestrian events just moments away, this is the perfect place to relax and recharge.

4.99 out of 5 average rating, 104 reviews

A spacious heated pool is surrounded by travertine decking, with lounge chairs and a shaded umbrella positioned for relaxation. Lush tropical plants and trees create a private atmosphere, while a grill is nearby for outdoor cooking.

Home in Flamingo Park

Chic Home w/ Saltwater Pool Near Beach + Downtown

This historic Flamingo Park home has been completely revamped, boasting contemporary finishes, minimalist decor, a custom Italian kitchen + a large outdoor space, ideal for wining & dining. The heated saltwater pool includes steps where you can relax w/ a cocktail + space for swimming - perfect for the entire family. Only steps from chic restaurants, cafes, the Norton museum & both the Kravis + Convention Centres. On top of that, you're only minutes away from world-class beaches & downtown WPB!

Superhost

A spacious pool area features a heated saltwater pool surrounded by tropical foliage and sun loungers. An outdoor dining area with a table and chairs invites relaxation, while the open concept living area showcases bright decor and ample natural light from large windows.

4.79 out of 5 average rating, 301 reviews

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.

A screened-in patio highlights a clear blue pool surrounded by tropical landscaping. Lounge chairs are positioned nearby, and a child safety fence secures the area. The structure provides an inviting environment for relaxation with abundant natural light filtering through the screens.

4.99 out of 5 average rating, 122 reviews

*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!

4.98 out of 5 average rating, 132 reviews

A vibrant pink pool float with the text 'OUT OF OFFICE' is placed in the clear blue water of a private swimming pool. Additional pool floats in various colors are visible, creating a playful atmosphere. Lush greenery surrounds the pool area.

Home in Lake Worth

Tranquil Vibes ~ Pet Friendly Private Pool Home

Welcome to our cozy pool home with screened porch, deck w/ remote control lighting of cabana for evenings. Grill, tropical fruit trees, plants & private fenced yard. Coastal cottage decor mixing vintage finds in newly remodeled space. Neighborhood is peaceful w/ close drive to beaches, restaurants, golfing, parks & shopping. Each bedroom has cooling mattress pads & ceiling fans. Pets welcome! Beach chairs, cooler, bikes, beach umbrella, pool floats, yoga mat, games/books-.Long stays welcome

Superhost

An unheated swimming pool with clear blue water is surrounded by a fenced patio. Lush palm trees frame the area, providing a tropical feel. The sunny sky enhances the serene atmosphere of the backyard space, with green grass visible in the background.

Bungalow in Wellington

4.84 out of 5 average rating, 115 reviews

Cozy waterfront king-bed bungalow in Wellington

Spacious 2150sqf waterfront pool house! Three charming French doors are leading from the master bedroom, dining and living rooms to a serene back patio with a view of the pool and waterfront. Minutes from the IPC, Equestrian centers, the Green Mall, and many restaurants and shops. 20 minutes from the ocean. Bring the whole family to this peaceful place with lots of room for fun and relaxation. For the fans of fishing, there is a rod with accessories in the garage for you to use and enjoy.

A spacious outdoor patio features a shimmering pool surrounded by lounge chairs and a relaxing hot tub. Colorful pool floats are positioned in the water, while a shaded seating area offers comfortable furnishings. Lush greenery and a clear sky enhance the serene atmosphere.

5 out of 5 average rating, 13 reviews

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.

4.81 out of 5 average rating, 181 reviews

A spacious screened-in pool area is shown, featuring a clear blue pool with steps leading in. Lounge chairs are positioned along the perimeter, and the surrounding deck is framed by wooden beams, allowing sunlight to filter in. Lush greenery can be seen beyond the enclosure.

Home in West Palm Beach

Grand Hacienda • Sleeps 32 • Celebrate Together

Private 4‑acre estate. Superhost since 2018 with all‑white cotton bedding, mattress & pillow protectors for a clean, comfortable stay. Sleeps up to 32 with tennis, pickleball, basketball, soccer, volleyball, golf/batting cage, ninja gym, ping pong & a large screened pool with BBQ. Just 15 min or less to Palm Beach Airport, beaches, malls, golf, fairgrounds, major highways, Kravis Center, convention center, and downtown Palm Beach & Wellington — perfect for group stays and celebrations.

An open-concept living area showcases a warm blend of neutral tones and wooden accents. Comfortable seating is arranged on a textured area rug, complemented by a dining table in the background. A kitchen with modern appliances and wooden cabinetry can be seen, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 37 reviews

Sunny De-Lite / Equestrian Center / Wellington

Welcome to your all-season retreat. 1 week or 6 months in this relaxing, open, pool home. Spend your days at the Winter Equestrian Festival (WEF), which is only a short 3-mile drive away. Relax away your evenings in the screened-in lanai or outside by the pool. The 3 bedrooms are cozy with space for all your travel necessities. The den / TV room gives you all the space needed to spread out and be comfortable. Get ready to enjoy this recently updated, 100% refurnished home.