Holiday rentals with a pool in Wailea

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Top-rated rentals with a pool in Wailea

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

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Top guest favourite
The exterior of the end unit on the second floor is showcased, featuring a light-colored facade with green accents. Lush tropical plants surround the base, and a set of stairs leads to the entrance, providing a sense of privacy.
Flat in Kihei
4.94 out of 5 average rating, 145 reviews

Private Top-Floor Apartment with Mountain and Ocean Views

Many units in the Palms only have air conditioning in the master bedroom. We substantially upgraded the unit (new floors, cabinets, appliances), and while we were at it we installed AC throughout the unit. -Unit #906 -Beautiful Views -End Unit on Second Floor Provides Awesome Privacy -Air conditioning throughout unit...3 zones -Private Lanai With It's Own Weber Gas BBQ -2 Lounge Chairs -Quiet Location -All New Appliances -Brand New Full Sized Washer And Dryer -Luxury King Bed In The Master Bedroom -2 Twin Beds In The Second Bedroom can Also be Converted into a King Sized Bed -Free WiFi Internet -Free Local And Long Distance Phone Calls Within US And Canada -Pullout Sleeper Sofa -Fully Equipped Kitchen With BBQ Platters And Utensils -Flat Screen TV In The Living Room -Pac-n-Play and Booster Seat for young ones -Keawakapu Beach just a short walk away -Tommy Bahama Beach Chairs -Boogie Boards -Beach Umbrella -Beach Coolers -Pool / Beach Towels -Large Pool Area -Hot Tubs The entire condo and grounds are yours to enjoy. Wonderful pool and spa just a 2 minute walk from the unit. My On-Island Representative is available when needed. She lives in Kiehi and is handles several units for me. You will receive her phone number and email address upon booking the unit. Rest assured someone is on call should you need help. If golf, shopping, and being pampered is the aim, then Wailea is ideal. Walk to Keawakapu, one of Maui’s best beaches, play at 3 championship courses at Wailea Golf Club, and choose from 3 top spas. For an ocean adventure, rent an outrigger canoe. One dedicated parking spot just outside the front door to your condo. Multiple first come first serve parking spaces 40 feet away from this spot. We provide beach gear (chairs, umbrella, boogie boards, cooler) and baby gear (booster seat, pack n play).

Top guest favourite
The image captures a vibrant sunset over the ocean, with hues of orange, pink, and purple reflected across the water. Silhouetted palm trees line the foreground, adding a tropical feel. The landscape features rocky shorelines and gentle waves under the colorful sky.
Apartment in Wailea
4.99 out of 5 average rating, 134 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and bi-coastal oceanfront views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (806) and includes two-bedroom suites on the world-famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent snorkeling, body surfing, whale watching, scuba diving, paddle boarding, and kayaking literally at your doorstep

Top guest favourite
Apartment in Kihei
4.99 out of 5 average rating, 126 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

Top guest favourite
A stunning beach scene captures vibrant sunset colors reflecting off wet sand. Rocky outcrops frame the tranquil waters, while palm trees sway gently in the foreground. Wispy clouds stretch across the sky, adding depth to the evening landscape.
Apartment in Kihei
4.99 out of 5 average rating, 181 reviews

Romantic, Luxury Retreat w/Ocean View-Couples Only

Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Not suitable for children or infants.

Top guest favourite
A bright living area offers ocean views through expansive sliding glass doors. Comfortable chairs are positioned towards the balcony, where coastal scenery includes palm trees swaying in the breeze. Neutral decor is accented with beach-themed cushions, and a TV set is present on a stylish console.
Apartment in Wailea
4.99 out of 5 average rating, 216 reviews

Mana Kai 608: Oceanfront Remodel Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY ON Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, on the border of Wailea and Kihei! Our condo is designed with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5 star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best Property Manager in Maui, Tracy O'Reilly to take amazing care of you!

Top guest favourite
A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.
Apartment in Kihei
4.99 out of 5 average rating, 255 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Top guest favourite
A modern kitchen and dining area are visible, featuring a round table set for four with woven placemats and plates. Stainless steel appliances are arranged in the sleek kitchen design, while large sliding glass doors open to reveal views of lush gardens and the ocean beyond.
Apartment in Wailea
4.96 out of 5 average rating, 169 reviews

A.R.A Retreats: Big Blue Pacific

Nicknamed “Big Blue Pacific” for its absolutely stunning view of the Pacific Ocean from the living room, kitchen and master bedroom. Our vacation rental condo is located in Wailea Ekolu, the well-known luxury resort community of Wailea. It offers a relaxing space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views and when the sun goes down, watch your favorite shows on on our smart tvs!

Guest favourite
A spacious living area is characterized by wood-paneled walls and natural light from large sliding glass doors. A comfortable queen-sized sleeper sofa and two accent chairs are arranged around a coffee table. A flat-screen smart television is mounted on the wall, adorned with complementary artwork.
Apartment in Kihei
4.9 out of 5 average rating, 110 reviews

Luxury Condo in Wailea Ekahi w/Direct Beach Access

Do you want direct and private access to probably the best beach (i.e. Keawakapu) on Maui? Then look no further than our unit in the Wailea Ekahi complex! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. You are also in walking distance to the stores and restaurants at the Shops at Wailea and also the Wailea Beach Path. This condo has everything you need to make your Maui experience memorable, luxurious, and convenient.

Top guest favourite
A serene landscape view features tropical greenery and palm trees leading to the ocean. Sun umbrellas are visible along the shore, providing shade, while calm blue waters stretch into the distance. Lush foliage surrounds the area, enhancing the tranquil outdoor environment.
Apartment in Kihei
4.96 out of 5 average rating, 144 reviews

Wailea Ekahi Oceanfront, 300 FT To Keawakapu Beach

Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

Guest favourite
Home in Kihei
4.96 out of 5 average rating, 455 reviews

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Top guest favourite
The living area is arranged with comfortable seating over a textured carpet. A low coffee table holds decorative elements, while art adorns the wall and a modern kitchen with stainless steel appliances is visible in the background, enhancing the open layout.
Apartment in Wailea-Makena
4.98 out of 5 average rating, 150 reviews

130K Hawaiian Reno on Wailea Blue Golf *Ocean View

BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.

Guest favourite
A modern kitchen features sleek white cabinets and a spacious granite countertop, with stainless steel appliances. A decorative arrangement of tropical flowers is positioned on the counter. A sliding glass door leads to a private lanai with ocean views, furnished with a dining table and chairs.
Apartment in Wailea
4.96 out of 5 average rating, 188 reviews

Wailea Gem-Remodeled Ocean View

Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.

Popular amenities for Wailea rentals with a pool

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Quick stats about holiday rentals with a pool in Wailea

  • Total holiday rentals

    Explore 1,870 holiday rentals in Wailea

  • Nightly prices starting at

    Wailea holiday rentals start at £74 per night before taxes and fees

  • Verified guest reviews

    Over 49,550 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,050 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    1,040 properties have a dedicated workspace

  • Wifi availability

    1,870 of Wailea holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wailea rentals

  • 4.8 Average rating

    Wailea stays are highly rated by guests – averaging 4.8 out of 5!

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