
Holiday rentals with outdoor seating in Wailea
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Quick stats about holiday rentals with outdoor seating in Wailea

Total holiday rentals
Explore 840 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $189 NZD per night before taxes and fees

Verified guest reviews
Over 34,170 verified reviews to help you choose

Family-friendly holiday rentals
480 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
810 properties feature pools

Rentals with dedicated workspaces
540 properties have a dedicated workspace

Wi-Fi availability
840 of Wailea holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wailea rentals

4.9 Average rating
Wailea stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated Holiday Houses with Outdoor Seating in Wailea
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Wailea Beauty - walk to the beach & shops
Our locally-owned, newly redesigned 2BD/2BA modern Maui condo is located on the award-winning Wailea Blue Golf Course at The Grand Champions Villas. The Villas are nestled in the heart of tropical Wailea; minutes from shopping, tennis, restaurants and pristine beaches. Stroll to upscale boutiques and restaurants, or take a short walk to some of the most beautiful beaches in the world. Our condo features local Hawaii art and is your perfect home away from home on the beautiful island of Maui.

Sweeping Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

Luxurious Condo in South Kihei
Beautiful fully renovated condo. Located in Maui Kamaole, the best resort complex in South Kihei. Walking distance to the beach, shops, restaurants and bars. This condo has everything a renter needs during vacation. Full kitchen, washer and dryer, beach gear, towels, bedding and more. The complex has two swimming pools, barbecues, tennis courts and outdoor picnic areas. This location is next to fun activities such as swimming, snorkeling, diving, surfing, kayaking, fishing, and more.

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.

Modern Renovated Palms at Wailea Condo!
MODERN CONDO WITH ATTENTION TO DETAIL! Our bright, modern island condo awaits you! Breathe easy knowing that you have everything at your fingertips. Enjoy your morning coffee on the large lanai. Pack a beach bag and head to one of the best beaches just a 10 minute walk away. Explore the Shops at Wailea. You will feel right at home cooking in our fully equipped kitchen. Close out your day by watching the sunset from the pool area and then stargazing on the lanai. Then repeat!

Luxurious Wailea Ocean Vistas
Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful lushness while enjoying a charming well-designed hideaway. We have considered every detail to provide the most effortlessly luxurious stay possible. With beaches nearby and two pools onsite, this island paradise has everything and more.

Luxury Condo w/wide Ocean View (Palms at Wailea)!
There is no better location than Wailea to experience your Maui vacation! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. This condo is only a short walk to one of the best beaches (Keawakapu) on Maui and is also in close proximity to the Shops at Wailea. We spared no expenses in stocking this condo with everything you need to make your Maui experience memorable and luxurious.

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
Welcome to Happy Everything! Wailea Ekolu Complex A fun, fully re-modeled, well appointed and comfortable townhome situated on hole 10 of the famous Wailea Blue Golf Course at beautiful Wailea, Maui. Comfortably sleeps 6. Spectacular views of the Ocean and Neighbor Islands. Close to beaches, shopping, restaurants, Wailea Resorts and just a chip shot away from the golf course and brand new Wailea Village shops.

*Fully Remodeled* Modern Island Style*
I am looking forward to hosting you at the Palms at Wailea 606 and making your vacation fun and enjoyable. The Palms is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all within a few minutes. I offer you a clean, comfortable and memorable stay on the island. I want to make your Maui dreams come true! Mahalo and looking forward to seeing you! -Aini

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.

Ocean/Golf Course Views, Tropical Resort in Wailea
Breathe in and exhale slowly while gazing at serene greenery and misty mountaintops. Make the most of a country-club setting by lounging on sun decks and swimming in heated pools. Retreat to an updated condo to unwind and fall asleep in a comfy bed. (This unit is suitable for a maximum of four (4) guests. Infants of any age are counted as guests.)

Wailea Surf Shack: Golf, shopping & beaches!
Welcome to Wailea Surf Shack, a beautifully renovated Maui retreat in the heart of Wailea. Book with confidence knowing that we live on the island, personally manage and care for the condo, and truly treat our guests like family. We go above and beyond to make sure your stay is comfortable, relaxing, and filled with wonderful Maui memories.
Popular amenities for Wailea outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Cajudoy's Hale - STKM 2O13-OO18 / TA-081-709-8752-01

South Maui Guesthouse

Go for an Ocean Swim From a Fun Beach Villa

12 Minute Walk Kamaole Beach II-Quiet Private Easy

Oceanview Home with Private pool and hot tub

Cozy Beach House in Kihei BBKM 2018/0002

Stunning ocean view Villa, Heated pool, Wailea

NEW! 1 bed | Walk to town/beach (S. Kihei)
Apartment rentals with outdoor seating

Maui Banyan 1bd steps to beach & restaurants

Ocean View, 1 minute walk to the beach 2BR/2BA

Beautiful Studio Oasis Maui Banyan

Ocean Front With Ocean View! AC, King Bed, 2 Bath!

Next to Beach, Foods & Shops - Updated w/ View!

Ocean Front Vibes Maui

Maui Oceanfront Penthouse at Nani Kai Hale (609)

Spring Special / One Bedroom- Closest to beach!
Condo rentals with outdoor seating

Coastal Dream Oceanfront Condo!

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Maui Banyan 1bd/2ba, AC, quite, steps to the beach

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

Luxury Vacationing Modern Condo Aug Specials $349

Mana Kai 608- Oceanfront Thanksgiving Now OPEN!

Grand Champions 169 Beautiful 3 BR on the Fairway!
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $652 NZD | $681 NZD | $604 NZD | $530 NZD | $473 NZD | $489 NZD | $471 NZD | $447 NZD | $432 NZD | $466 NZD | $525 NZD | $640 NZD |
| 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 |
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- Maui
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