Vacation 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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Guest favorite

Guesthouse in West Palm Beach

4.99 out of 5 average rating, 154 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

Nov 26 – Dec 3

R4,328 ZAR per night

Guest favorite

Home in Boynton Beach

4.89 out of 5 average rating, 161 reviews

CASA DE CONCHA - 3/2 POOL Home in Boynton Beach!

Conveniently located in central Boynton Beach with easy access to both I-95 and the FL Tpk, and only 4 miles to the beach, this charming and tastefully appointed 5 * rated 3/2 pool home offers exceptional comfort (new mattresses, loaded with amenities), leisure (private enclosed pool, outdoor dining area, fire pit), AND utility (fully equipped kitchen, grill, home office) for families and business travelers alike! Come stay with us and enjoy the benefits of an EXPERIENCED SUPERHOST-managed home!

Jun 4 – 11

R2,212 ZAR per night

Guest favorite

Home in Wellington

4.8 out of 5 average rating, 289 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.

Nov 9 – 16

R4,068 ZAR per night

Guest favorite

Guest suite in West Palm Beach

4.84 out of 5 average rating, 660 reviews

Private apartment/2 rooms/2 beds/ 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.

Jul 23 – 30

R1,718 ZAR per night

Guest favorite

Condo in Palm Beach

4.98 out of 5 average rating, 156 reviews

The Lilly Pad: A Lilly Pulitzer- Inspired Condo

Welcome to THE LILLY PAD- Palm Beach's 1st Lilly Pulitzer-inspired condo!! The Lilly Pad is decked out in all things Lilly Pulitzer and is the perfect place to come stay and play Palm Beach-style. Located in the historic Palm Beach Hotel, The Lilly Pad, is a few blocks from the beach (we've got the beach towels, chairs and umbrella!) and steps away from some of the best restaurants, shopping and nightlife in Palm Beach. We have beach cruisers and a parking pass for all of our guests to use too!

Oct 27 – Nov 3

R3,714 ZAR per night

Guest favorite

Home in Wellington

4.99 out of 5 average rating, 107 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!

Aug 15 – 22

R5,957 ZAR per night

Guest favorite

Guest suite in Lake Worth Beach

4.97 out of 5 average rating, 275 reviews

Quiet Private Studio w/Pool for One Guest

My Quiet/Private & Beautiful Studio w/ pool is perfect for a single nonsmoking petless professional, golfer, nurse/med student on rotations in Palm Beach centrally located to all area hospitals, the county's many diverse golf courses & the Wellington equestrian community. Private Entrance w/ illuminated off street parking spot, large brand new stone embellished bathroom, granite countertop, mini Kitchen w/ fridge, microwave, and coffee are just a few upscale ammenities inherrent in my place.

Aug 20 – 27

R1,925 ZAR per night

Guest favorite

Condo in Palm Beach

4.93 out of 5 average rating, 188 reviews

🌞🌴🏖 Pool View Palm Beach Studio w/Parking⚡wifi

AMAZING LOCATION! NO CAR NEEDED! Beautiful updated Palm beach island direct pool view 275 sf. studio available in the historic Palm Beach Hotel. street 2.5 blocks from the beach with a free parking permit for unlimited parking nearby! A deluxe newly updated and renovated condo complete with NEW king size bed, wardrobe, , kitchenette and a great view of the pool! Restaurants, bars & beach within 1-3 blocks with a Publix grocery store across the street. Pool, patio, and gardens are all on site.

Jun 22 – 29

R1,812 ZAR per night

Guest favorite

Guesthouse in Wellington

4.98 out of 5 average rating, 163 reviews

Comfy Cottage -1 Bed 1 Bath-No cleaning fee

A delightful 800 sq ft. 1BR, 1BA standalone cottage (King size Sleep Number). Shared pool located in tropical setting on acre prop. 8 ft. sliders in bedroom and living room -look out over backyard/pool area from your own screened porch. High ceilings with skylights and large rooms provide airy comfort. 3 miles to Equestrian, 20 min. to beaches & PBIA. West of WPB but central to all of Palm Beach Co. Great shopping and dining very near. Perfect location. NO children under 13 - no exeptions

Jul 14 – 21

R2,691 ZAR per night

Guest favorite

Guesthouse in West Palm Beach

4.97 out of 5 average rating, 327 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.

Sep 1 – 8

R2,610 ZAR per night

Guest favorite

Home in Wellington

5.0 out of 5 average rating, 18 reviews

Sunny De-Lite / Equestrian Center / Wellington

Welcome to your winter 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 combo TV room/4th bedroom gives you all the space needed to spread out and be comfortable. Get ready to enjoy this recently updated, 100% refurnished home.

Jul 16 – 23

R5,792 ZAR per night

Superhost

Condo in Palm Beach

4.78 out of 5 average rating, 381 reviews

Palm Beach Island Pool Studio 3 Blocks to Beach!

Welcome to Palm Beach Island! Check into this gorgeous remodeled condo efficiency 2 blocks from the beach! Gorgeous pool, restaurants, cafes, shopping and parks! Enjoy Palm Beach Island as you are within walking distance to everything, or rent a bike and hop on for a ride! Located in the Historic Palm Beach Hotel, you are half a mile from downtown West Palm Beach. FREE VALET PARKING

Oct 8 – 15

R2,607 ZAR per night