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

Home in Kihei

4.96 out of 5 average rating, 409 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

Guest favorite

Condo in Kihei

4.96 out of 5 average rating, 104 reviews

Romantic Beach Retreat, New King Bed & A+ Wi-fi

Hale Kamaole: Romantic Bright & Airy Beach Condo Across The Street from Kamaole III Beach in South Kihei! Tasteful heritage decor, fast internet, King bed, walk-in shower, 1st floor unit. Perfect for couple's getaway, anniversaries, honeymooners. Washer/Dryer. Spacious lawns & tropical gardens w/ 2 pools, Tennis court & BBQ grills. Popular snorkeling area. Eddie Pu walking trail w/ plenty of wildlife just steps away. Walk to shops & restaurants.Free Parking Pass NB:17.712% Hawaiian Transient Tax

Guest favorite

Condo in Wailea-Makena

4.94 out of 5 average rating, 261 reviews

A.R.A Retreats: The Molokini

FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful 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

Guest favorite

Condo in Wailuku. Maui

4.87 out of 5 average rating, 261 reviews

Oceanfront Condo. Pool & Spa, 1 Br.

MAALAEA OCEANFRONT. Oceanfront lawn, panoramic views, full kitchen, washer/dryer, granite counters, oceanfront lanai, all supplies, beach gear, quiet... with pool, jacuzzi/spa, BBQ, TempurPedic queen bed, desk, free wi-fi & parking. Nearby uninhabited 5 mile long beach walk & swim, Rooms have fans and windows /screens that allow cooling breezes along with one A/C unit Peaceful Maalaea neighborhood. Centrally located to explore Maui, 15 minutes to airport. Adults(2) only. No smoking.

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 169 reviews

Mana Kai 608- Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on incredible Keawakapu beach! This location is ideal, right 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.

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 142 reviews

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.

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 104 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and ocean front views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (unit 806) that 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 body surfing, whale watching, snorkeling, scuba diving paddle boarding and kayaking literally at your doorstep.

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 170 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.

Guest favorite

Condo in Wailea-Makena

4.94 out of 5 average rating, 104 reviews

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

This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!

Guest favorite

Condo in Wailea-Makena

4.98 out of 5 average rating, 117 reviews

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.

Guest favorite

Condo in Kihei

4.91 out of 5 average rating, 191 reviews

Renovated Penthouse Studio @ Maui Banyan (NICE!)

This freshly remodeled 1 bath studio penthouse in Maui Banyan is a very popular vacation getaway, conveniently located in South Kihei, just a short walk away from the beautiful Kamaole Beach Park II and the nearby shops and restaurants. The grounds are beautifully landscaped & exceptionally well-maintained, offering 2 swimming pools, 2 hot tubs, a tennis court & 2 outdoor BBQ areas.

Guest favorite

Condo in Wailea

4.97 out of 5 average rating, 152 reviews

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.