Holiday rentals with a pool in Wellington

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Wellington

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite

Guest house in Flamingo Park

4.97 out of 5 average rating, 177 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

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.

Guest favourite

Farm stay in Wellington

4.92 out of 5 average rating, 26 reviews

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.

Top guest favourite

Home in Flamingo Park

4.99 out of 5 average rating, 105 reviews

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

Home in Wellington

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.

Top guest favourite

Home in Wellington

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!

Top guest favourite

Home in Lake Worth

4.98 out of 5 average rating, 133 reviews

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

Top guest favourite

Guest house in Flamingo Park

4.98 out of 5 average rating, 452 reviews

Key West Style Suite with Pool/Spa

This beautiful Key West Style studio with kitchen and WIFI is located in the historic neighborhood of Flamingo Park. It’s close to restaurants, downtown Rosemary Square, the Norton Art Museum, the WPB Convention Center, the Palm Beach International Airport, the instracoastal waterway and 5-10 minUte drive to Worth Avenue in Palm Beach and the Palm Beaches. We welcome couples, solo adventurers and business travelers who can enjoy a private backyard guest suite with salt water pool and spa.

Guest favourite

Bungalow in Wellington

4.84 out of 5 average rating, 116 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.

Guest favourite

Home in West Palm Beach

4.98 out of 5 average rating, 161 reviews

Bio Hacker Bliss! Pool, Sauna, Cold Plunge, HotTub

West Palm Beach Oasis! Explore a luxurious 3BR/2BA resort-style escape that sleeps up to 8 guests. Relax by the sparkling pool, unwind in the sauna, or enjoy movie nights at the outdoor theater. The game room & Tiki Bar make this the ideal spot for entertainment. Stylish decor, an 85" Smart TV, & modern amenities create the ideal setting for relaxation. At Russi Retreat, you're not just booking a stay; you're securing a private sanctuary in South Florida. Book your stay today!

Top guest favourite

Home in Wellington

4.97 out of 5 average rating, 38 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.

Guest favourite

Home in Royal Palm Beach

4.87 out of 5 average rating, 151 reviews

Big Pool House/ Great Area/ 3bdrms and 2 baths

Beautiful 1 story Home. POOL , SMALL CANAL IN THE BACK 3 bdrms+ 2 full bathrms 8 guests. Pet friendly (Max 2 dogs) Great for families looking for a peaceful getaway. Bbq grill (propane provided). Great location! 15- 20 minutes from downtown WPB and Palm Beach International. Easy 25- 30 minutes access to closest beach. Shops, Restaurants, Target: 5 - 10 minutes away. Parking on premises 3 cars on driveway. POOL NOT HEATED. NO HOT TUB ON PREMISES. $50 PET FEE/PER PET