House vacation rentals in Wailea, Wailea-Makena

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Top-rated house rentals in Wailea, Wailea-Makena

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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

Sep 19 – 26

G$107,456 GYD per night

Guest favorite

Home in Kihei

4.98 out of 5 average rating, 102 reviews

Mana Hale Vacation Rental

This private home is nestled in a beautiful garden just 1 mile from the ocean. The house is spacious with 2 bedrooms & 2 full bathrooms. Front and back decks offer ample opportunity for lounging with a good book, grilling, visiting with friends and family or even just a romantic getaway. The house is close to cafe's, shopping, restaurants and many of the idyllic maui beaches. Perfect for retreat, fun and healing in paradise. STKM 2018/0002 HITax # GE-087-066-3168-01 HI TAT # TA-087-066-3168-01

Dec 15 – 22

G$125,689 GYD per night

Guest favorite

Home in Kula

4.91 out of 5 average rating, 303 reviews

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela (owner/host) has been hosting two fully permitted listings for the last 10 years with over 1,000 five star reviews. BUT this one, Kula Jewel, burned to the ground in the Maui wildfires in August last year. We are in the process of rebuilding a GORGEOUS new home, and we are taking bookings for 2025, but we donʻt have photos yet. Iʻm including some photos of the STYLE of house we are building, but not the *actual* house. Ask about our special refund policy if we are not ready by Christmas!

Apr 13 – 20

G$67,477 GYD per night

Guest favorite

Home in Haiku-Pauwela

4.97 out of 5 average rating, 216 reviews

Live Like a Local; near Coffee, Road to Hana and Haleakala

Grab a coffee and drive to the beach to catch waves or watch sea turtles nesting in the sand. This peaceful home with a private yard, outdoor shower, and fun surfboard fence is a great base for exploring the Road to Hana or Haleakala. Located on the quiet north shore of maui, opposite side of island from the fire. Ideal for returning maui visitors who want to stay on the north shore or guests splitting their stay between 2 sides of the island of Maui. Sleeps: 4 Adults max plus 1 child under 12

Mar 22 – 29

G$78,388 GYD per night

Guest favorite

Home in Kihei

4.97 out of 5 average rating, 133 reviews

12 Minute Walk to Kam Beach II-Quiet Private Easy

This 1 bedroom/1 bath suite is a self contained, attached apartment (ohana or ADU) with private entry. Off street parking is 10 seconds from your door. A 12 minute walk to beautiful Kamaole Beach II, as shown in the photos. And... NO CLEANING FEE! Ideal Location, Quiet and Private. I am a SUPERHOST, see the 4.97 reviews and comments. INSTANT BOOK for a great stay. All fees and taxes are listed & collected when you book. There are no surprise or additional costs. Permit #BBKM 2O19/OOO2

Oct 27 – Nov 3

G$50,106 GYD per night

Guest favorite

Home in Kihei

4.94 out of 5 average rating, 200 reviews

The Maui Beach Ohana• Prime Location• Maui Vibes

Aloha! Updated Spacious Corner Villa! 1 Master- 1 Studio- 1 Bath •Downstairs- South Kihei Rd. Side- Corner Unit with Driveway Parking Connecting to a Private Entrance. •Our Ohana has everything you will need to make you feel at home. Private Deck Black out curtains Remodeled Kitchen Full size WASHER AND DRYER Xtra Linens A/C (2) LED- Mirror Vanity Black Rock Shower 5 Min walk to COFFEE & Restaurants 3 Min Walk- Beachs, Cove And Charley's Plenty of USB- 500+ Net Beach equipment & Boards

Apr 6 – 13

G$66,326 GYD per night

Guest favorite

Home in Lahaina

4.91 out of 5 average rating, 127 reviews

Kaanapali Cottage ICC 29 Indoor/Outdoor Living

International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

Sep 20 – 27

G$84,775 GYD per night

Guest favorite

Home in Kihei

4.87 out of 5 average rating, 130 reviews

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

WONDERFUL! Three bedroom hale (home) in the Central Kihei area of Maui. Wood floors, lots of space, kitchen fully stocked, BBQ and so much more. Great for kids, elderly, and young at heart. This house is your home away from home. We have all of the necessary items for a home. If we do not have something please let us know and we will try our best to accommodated. Walking distance to the beach, shopping, park, public transportation, etc... You will not find a better place in Kihei.

Nov 29 – Dec 6

G$92,372 GYD per night

Guest favorite

Home in Haiku- Pauwela

4.97 out of 5 average rating, 196 reviews

Hale Leialoha (BBPH 20 17/00 04,SUP 20 17/00 10)

Hale Leialoha (GE-046-437-3760-01, TA-046-437-3760-01) is a beautiful plantation style cottage located in "upcountry" Maui. Our Cottage is permitted for a total of 4 adults and up to 6 people. The cottage easily fits a family of 6 (4 adults & 2 children or 2 adults & 4 children or 3 adults & 3 children) (License # BBPH 2017/0004, SUP 2017/0010) As our guest, you will enjoy the modern finish and conveniences as well as a large roomy covered deck amidst the casual feel of old Hawaiiana.

Sep 17 – 24

G$81,490 GYD per night

Guest favorite

Home in Haiku-Pauwela

4.9 out of 5 average rating, 176 reviews

Spacious Private 3 BR Home: A/C, WiFi & CBL

Hale Roselani is a 2,000 sq ft private home, situated on a quiet family oriented culdesac just below the Pauwela Cannery in Haiku. It is equipped with everything you'll need while you are here on your Hawaiian holiday. The open floor plan with large windows & doors opening up to the spacious lani offers an inviting space to spend time with family & friends. Our place is great for couples, ocean & outdoor enthusiast, & families looking for a quiet getaway on Maui's charming North Shore.

Nov 8 – 15

G$81,748 GYD per night

Guest favorite

Home in Haiku-Pauwela

4.99 out of 5 average rating, 116 reviews

Charming Hoku Pauwela Breathtaking ocean views!

Located on the north shore of Maui, Hoku Pauwela (Maui County B&B Permit# BBPH 2019/0002 and Hawaii State TAT # TA-036-968-8576-01) is the ideal location from which to experience the northshore, upcountry, Haleakala crater, and the epic drive to Hana. Spacious, quiet, and family-friendly you'll have all you need to explore Maui and a peaceful living area to relax in after a day of adventuring.

Oct 12 – 19

G$102,248 GYD per night

Guest favorite

Home in Lahaina

4.98 out of 5 average rating, 123 reviews

Private 4bd Home, Walk to Beach

The Kahana Beach House is a spacious and comfortable home located across the street from a secluded beach. Close to some of Maui's best restaurants, golf, and exciting island attractions the beach house serves as a great central hub to explore the island of Maui. The fully equipped kitchen has everything you need and the outside deck is great for lounging in a hammock or grilling on the BBQ.

Mar 21 – 28

G$197,182 GYD per night