Holiday rentals with a pool in Wellington

Cottage in Lake Worth Beach

4.99 out of 5 average rating, 138 reviews

Private & Pet Friendly, Key West-King Bed Cottage

Spend your beach getaway at our cozy and colorful cottage. It’s one of the historic cottages of Lake Worth Beach listed in a bestselling book 'The Cottages of Lake Worth'. Sit back, soak up the sun, and enjoy the splash pool in the private yard, a palm tree paradise. Relax completely in the specious king-bed bedroom. In a walking distance from the cottage are the Lake Worth public beach and Downtown with a variety of restaurants and entertainment venues. Community Golf Club is around the corner.

Superhost

4.79 out of 5 average rating, 303 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.

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!

Guest house in Flamingo Park

4.98 out of 5 average rating, 460 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.

4.84 out of 5 average rating, 116 reviews

Bungalow in Wellington

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.

5 out of 5 average rating, 18 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.

4.98 out of 5 average rating, 164 reviews

Home in West Palm Beach

Bio Hacker Resort! Pool, Sauna, ColdPlunge, 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!

4.88 out of 5 average rating, 155 reviews

Home in Royal Palm Beach

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

5 out of 5 average rating, 26 reviews

New to Market - Wellington POOL Home!

Recently renovated gem in the heart of Wellington. Quiet neighborhood and all the amenities await you here at this stylish ranch style pool home. This home has 4 bedrooms and 2 bathrooms. The backyard is large and the heated pool is brand new. There is an outdoor dining table and a separate outdoor seating area for the entire family to enjoy. Minutes away from Polo grounds, Wellington Mall, Lion Country Safari, and only a 15 minute drive to Downtown West Palm Beach.

Home in Palm Beach Gardens

5 out of 5 average rating, 146 reviews

Heated Pool•Near Beach•Pet Friendly

Welcome to South Florida! You’ll feel like you are at your own private resort when you take a dip in the heated pool surrounded by tropical greenery and an ocean breeze. The 1,368 sq. ft. home features an updated open floor plan w/ large kitchen and bar to host friends & family. The prime location puts you minutes away from the best beaches, and just up the road from the best shopping, dining, and nightlife options. Quiet street! No parties!

Guest house in Flamingo Park

4.97 out of 5 average rating, 178 reviews

Tropical Cabana with Pool and Bedroom

Private poolside retreat with king bedroom, cabana, and lush tropical privacy. Enjoy a heated pool with waterfall, outdoor shower, BBQ grill, kitchenette, washer/dryer, and two smart TVs. Bedroom opens to patio; cabana includes futon, dining table, and kitchenette. Walk to shops, dining, and attractions, or explore West Palm Beach with complimentary bikes. Secluded yet convenient, perfect for relaxing or working remotely.