Vacation rentals with a pool in Wailea, Wailea-Makena

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Top-rated rentals with a pool in Wailea, Wailea-Makena

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Guest favorite

Condo in Kihei

4.96 out of 5 average rating, 226 reviews

Beautiful Modern Decor in a Light-Filled Condo

This ground floor unit is perfectly located and easily accessible to all the complex's amenities; sparkling clean pools, gas and charcoal bbq's (that are cleaned daily) and a tennis court. You also have your own personal lanai to enjoy the cool island breeze as you sip your morning coffee or afternoon mai tai! Natural light fills this open and spacious condo and which is completely decked out with all new furnishings including a King size CASPER mattress with premium bedding, queen size sleeper sofa with 6 inch memory foam mattress, a 50" LED Smart TV (so you can watch your favorite Amazon or Netflix shows) or use the blu ray player all while listening through a 36" Bluetooth sound bar. If you plan to cook we have a large, fully stocked kitchen with all brand new everything including: Calphalon pots and pans, Cuisinart knife set and Cuisinart coffee maker, pyrex, cooking utensils, bamboo cutting boards, rice cooker, blender, toaster, dishware, glassware, flatware, BBQ tools, and more; All BRAND NEW! Planning on some fun in the sun? We got you covered with beach towels, beach chairs, ice coolers, tennis racquets, and a bunch of pool and beach toys!! We also have 2 brand new Air Conditioning units (one in the living room and one in the master bedroom) to help you stay cool and comfortable! Need to do some laundry during your stay? No problem, our place has a Washer and Dryer inside the unit for your added convenience! Or are you an over-packer? We’ve got you covered with plenty of closet space, hangers, and dresser drawers. You have access to our whole condo which includes a washer/dryer inside the unit as well as all of the amenities including 2 pools, charcoal and gas BBQ’s and a tennis court. We want you to love staying in our place as much as we do so we are available as often or as little as you need! Feel free to message (or call!) us with any questions about our property, our favorite place to watch sunset, or where the best shave ice on Maui is! (Hint, it’s pretty close!) This condo is in the well-manicured grounds of Hale Kamaole. This is a family-friendly complex with sprawling grass lawns, a tennis court, swimming pool, and barbecue stations. Directly across the street is a large grass park and beach shoreline. We find that one of the best ways to explore and get around the island is by renting a car or for the more adventurous type a 4x4 Jeep. This way you are able to see all that Maui has to offer! Whether it’s the lavender farm or wine tasting up in Kula, checking out the world renown wind surfing in Paia or hiking to waterfalls along the road to Hana you will want to rent a car to take you to these beautiful locations! There is plenty of free parking directly outside of our ground floor unit as well as through the perimeter of the complex!

Oct 15 – 22

ﺩ.ﺇ1,081 per night

Guest favorite

Home in Kihei

4.96 out of 5 average rating, 389 reviews

Stunning ocean view, heated pool at home by Wailea

Last minute bookings 5 days before arrival, and week long stays are 10% off. 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

Oct 24 – 31

ﺩ.ﺇ2,044 per night

Guest favorite

Condo in Kihei

4.91 out of 5 average rating, 135 reviews

160KReno-Stunning Palms in Wailea Condo-Beach/Golf

Brand New 160K Renovation+Redecoration 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 floor condo with private lanai that overlooks the grass.King Master Bed with a private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel/take long tropical beach walk.BOOKINGS UP TO 365 DAY

Apr 7 – 14

ﺩ.ﺇ1,298 per night

Guest favorite

Condo in Wailea-Makena

4.95 out of 5 average rating, 172 reviews

A.R.A Retreats: The Waterfall

Nicknamed “The Waterfall” for its massive 105 inch by 65 inch peninsula with it large waterfall countertop, perfect for cooking and entertaining. This was the first time we had done this Waterfall feature in our unit. Located in Grand Champions Villas in Wailea. Guests can enjoy the spacious NEW condo that has everything you should need for your trip! Guests can enjoy the spacious and comfortable condo that has everything you should need for your trip--including smart TV's in each room :)

Dec 18 – 25

ﺩ.ﺇ2,778 per night

Guest favorite

Condo in Kihei

5.0 out of 5 average rating, 137 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

SPECTACULAR OCEAN AND SUNSET VIEWS, including outer islands from the living room and lanai. You'll enjoy drinks in the evening watching the incredible sunsets. The condo has been totally redecorated and upgraded. The kitchen and bathroom are newly remodeled with maple cabinets and elegant granite counter tops. There is a very comfortable king size bed, a well-stocked kitchen, central AC, bamboo floors throughout, and a washer / dryer. The Condo is owned and maintained by Maui residents.

Feb 20 – 27

ﺩ.ﺇ1,832 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 132 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.

Dec 25 – Jan 1

ﺩ.ﺇ3,755 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 131 reviews

Maui Dream Place at Maui Kamaole G-209, Ocean View

Maui Dream Place is our vacation home rental property in Maui, Hawaii. This two story condo has plenty of space for your family, plus hotel-style amenities which include access to two swimming pools, hot tubs and tennis courts. In our opinion, our condo has the best views of the sunset in Kihei. Our condo is located at Maui Kamaole, a luscious and vibrant Hawaiian vacation rental community set on a hilltop on the south end of Kihei located only 25 minutes away from Kahului Airport.

Oct 20 – 27

ﺩ.ﺇ2,158 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 114 reviews

Romantic, Luxury Maui Getaway with Ocean View

This is a luxury 1 bedroom 2 bathroom 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 Wailea Palms 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

Aug 3 – 10

ﺩ.ﺇ1,512 per night

Guest favorite

Apartment in Kihei

4.94 out of 5 average rating, 106 reviews

Wailea Couples Retreat, 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.

Apr 12 – 19

ﺩ.ﺇ1,897 per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 146 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on Keawakapu beach! This location is ideal, on the border of Wailea and Kihei. We have designed our remodel 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 come stay with us! We have hired the best Property Manager in Maui, Tracy O'Reilly to take care of our guests.

Sep 2 – 9

ﺩ.ﺇ2,993 per night

Guest favorite

Condo in Wailea

4.93 out of 5 average rating, 145 reviews

Stunning ocean view! 2/2 in the heart of Wailea

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 condo is in the Wailea Resort area, and does not infringe upon nor remove housing from the local neighborhoods of Maui.

Oct 9 – 16

ﺩ.ﺇ1,962 per night

Superhost

Condo in Kihei

4.79 out of 5 average rating, 99 reviews

Your Paradise Awaits at Sunny Kihei Kai Nani!

Step into your own private tropical oasis! This adorable ground floor unit is walking distance to one of the most incredible beaches on Maui with tantalizing turquoise blue waters of the Pacific! This condo boasts an open and airy living space you will love. Enjoy your favorite grilled meals al fresco on the Weber gas BBQ grill and table with seating for four, just steps from your lanai.

Jun 6 – 13

ﺩ.ﺇ627 per night