
Holiday rentals with a pool in Wailea
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wailea
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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).

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

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.

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.

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!

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.

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!

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.

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.

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

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.

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
House rentals with a pool

Kihei 533- A/C, Free Parking, and WiFi

Aloha Aku CoCoPalm2 Suite – Cozy Beachfront Escape

Stunning One Bd Partial ocean, AC, wifi,Pool C209

Oceanview Townhome • Modern • 2 Min Walk to Beach!

Oceanview Home with Private pool and hot tub

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet
Apartment rentals with a pool

Stunning Ocean Views

Spacious 3bd on Golf Course I Grand Champions 105

Coastal Dream Oceanfront Condo!

Full Ocean- Full Sunsets- Beaches at Royal Mauiian

Fabulous Ocean Views at Ho'okipa at Wailea Ekolu!

Turtle Cove Oceanfront Views Island Sands Resort

Wailea Ekahi • Walk to beach • Near quiet pool

Wailea Elua 2007 – Oceanview Luxury Condo
Other holiday rentals with a pool

Tropical Beachfront Paradise

Beach Front Wailea, Full Ocean View A/C, ELUA102

Stunning Wailea 2/2, AC, Upper Fl , walk to beach

Kihei Maui Getaway

Ohe'o || Wailea Ekahi Unit 28B || Lowered Rates

Gorgeous Condo in Wailea Ekahi Village!

Endless Ocean Views - 1bd/2 bath

Wailea Ocean View Escape
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £264 | £267 | £266 | £237 | £211 | £218 | £207 | £199 | £192 | £203 | £233 | £277 |
| Avg. temp | 16°C | 16°C | 16°C | 17°C | 18°C | 18°C | 19°C | 20°C | 19°C | 19°C | 18°C | 17°C |
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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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Polo Beach
- Wailea Beach
- Kapalua Bay Beach
- Ka'anapali Golf Courses
- Maui Ocean Center
- Hāmoa Beach
- Ulua Beach
- Black Rock Beach
- Old Lahaina Luau
- Big Beach
- Maui Vista Condominium
- Black Sand Beach
- Whalers Village
- Haleakala National Park
- Maui Sunset
- Peahi
- Maui Arts & Cultural Center
- Kihei Kai Nani
- Kahana Beach




