
Vacation rentals with outdoor seating in Wailea
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Top-rated outdoor seating rentals in Wailea
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

100KContemporaryHawaiian Reno in Wailea-Beach/Golf
Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with private wrap around lanai. King Master Bed with a contemporary private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel or take long tropical beach walks.BOOK UP TO 365 DAYS

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.

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views
Location and views are everything when it comes to this home. Nestled in the heart of Wailea, most consider the beautiful area of Maui. This RARE 3br/2ba villa has enough space for a large family or a group of good friends. Just a short walk to some of the most beautiful beaches in the world, World class shopping mall and 5 star resorts. Enjoy all the comforts of home while taking in breath taking Grand views of the Deep Blue Pacific, Hole 2 of the Blue Wailea Golf Course and Mount Haleakala.

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.

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.

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.

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.

A.R.A Retreats: Garden Oasis
Nicknamed “Garden Oasis” for its beautiful little garden walk out off the Lanai onto a beautiful field. While it also has a amazing view of the pacific ocean the beautiful private walkout really set the tone for a relaxing and private oasis. Wailea Ekolu Village is a three-minute drive or 18 minute walk to the beautiful golden sands of Wailea Beach. The Shops at Wailea, Monkeypod Kitchen and so much more just a short walk away!

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

Wailea Ekolu Village 2/2 with stunning ocean view!
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.

*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

Stylish 1 br. gr. floor unit. Steps from the beach
Discover an exceptional South Maui escape just steps from the pristine sands of Kamaole III Beach, one of Kihei’s most celebrated stretches of shoreline. This elegantly furnished 800 sq. ft. residence offers a refined yet relaxed island experience, ideal for up to four guests seeking comfort, convenience, and an unbeatable location. Both short and long terms stays are available.
Popular amenities for Wailea outdoor seating rentals
House rentals with outdoor seating

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

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

South Maui Guesthouse

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

12 Minute Walk Kamaole Beach II-Quiet Private Easy

Oceanview Townhome • Modern • 2 Min Walk to Beach!

40% off monthly stay! 4 Bed Family Home (Kihei)

PAIA HALE Walk to beach and town
Apartment rentals with outdoor seating

Mavi Bay luxury ocean view condo

Oceanview Remodl, Sleeps 8 @ Kam 2, Pool, HTub, 5 Star!

Stunning Luxury Oceanview Condo

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

Updated 1st Floor Maui condo

Endless Ocean Views - 1bd/2 bath

Wailea Ocean View Escape

Next to Beach, Foods & Shops - Updated w/ View!
Condo rentals with outdoor seating

Fully remodeled, Ocean View, 3 mins walk to beach

Coastal Dream Oceanfront Condo!

Oceanfront Getaway, Brand New, Steps To Beach

Fabulous Ocean Views at Ho'okipa at Wailea Ekolu!

Spectacular Beachside 2BR+2BA at Maui Kamaole

☀Very Desirable South Kihei | Enlivening Getaway ☀

Grand Champions 169 Beautiful 3 BR on the Fairway!

Beautiful Palms At Wailea #608-Mar./April specials
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$70,555 GYD | G$72,845 GYD | G$72,845 GYD | G$64,103 GYD | G$57,235 GYD | G$59,108 GYD | G$57,027 GYD | G$54,113 GYD | G$52,240 GYD | G$56,403 GYD | G$63,479 GYD | G$77,423 GYD |
| 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 vacation rentals with outdoor seating in Wailea

Total vacation rentals
Explore 770 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at G$22,894 GYD per night before taxes and fees

Verified guest reviews
Over 31,530 verified reviews to help you choose

Family-friendly vacation rentals
430 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
730 properties feature pools

Rentals with dedicated workspaces
520 properties have a dedicated workspace

Wi-Fi availability
770 of Wailea vacation rentals include wi-fi 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
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