
Vacation rentals with a pool in Kihei
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Top-rated rentals with a pool in Kihei
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Spacious garden oasis near Maui's best beaches!
Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located next to Keawakapu Beach and minutes to Wailea. Our condo is perfectly suited for couples and small families wanting space with stylish comfort in a prime location. Relax on a luxurious king-sized bed, sectional sofa w/ memory foam sleeper, and a pack and play for toddlers! Enjoy the essentials of modern connectivity, a fully stocked kitchen, with two full bathrooms. Unwind in paradise on two lush garden patios!

'E Komo Mai' ! 1 Bed/1 Bath in Tropical Gardens
Across the street from Kalepolepo Beach this 621 sqf. condo is nestled in the tropical Zen gardens of Kihei Resort and features a spacious lanai. The one-bedroom unit was completely renovated and has all amenities including a Queen bed in the bedroom and a futon sleeper in the living room, fully equipped kitchen, WiFi, Samsung Smart TV, keyless entry, indoor laundry, designated parking, beach equipment (chairs, towels, toys, Snorkel gear) Pool and Hot Tub. Please inquire for special rates.

Coastal Dream Oceanfront Condo!
Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

Oceanfront, Beautiful View, Newly Renovated!
Our Maui vacation home is a beach front condo on the FOURTH floor in Kauhale Makai on the beach side of South Kihei Rd, steps to the beach. Beautiful ocean views from both bedroom and living room and features hotel-style amenities; an adult pool, kiddie pool, large hot tub, putting green, shuffleboard and free parking. Recently remodeled, our condo has central air-conditioning and easy access to all parts of the island! All taxes are included in the price. Ta-163-430-2464-01 (TAT LICENSE)

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.

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 have maple cabinets and elegant granite counter tops. There is a comfortable king size bed, a well-stocked kitchen, central AC, with all new bamboo floors throughout, and a new washer / dryer. The Condo is owned and maintained by Maui residents.

<2 min to Beach! Kihei Condo w/ Ocean View and AC
This updated, partial oceanview, modern 1 bed 1 bath condo comes equipped with a fully set up kitchen, California king sized bed, full size washer/dryer, TV, beach gear, internet, shared jacuzzi and pool, and (NEW) AC in the bedroom! Enjoy watching the whales during season, viewing the Maui sunset, and relaxing with a beverage and a book on the large lanai in the front of the condo. Located in North Kihei across from Kalepolepo Beach Park, this small complex is a peaceful Maui gem!

Newly Renovated Corner Unit w/ View at Maui Vista
Aloha - welcome to your Maui escape! Just steps from the iconic Charley Young and Kamaole I beaches, our newly remodeled condo offers comfort and convenience, with amazing dining and drink options a short walk away. Enjoy fresh seafood, tropical cocktails, and all the island vibes. Thoughtfully designed and continuously updated, our space has everything you need for a relaxing, unforgettable stay. Book your tropical getaway today—we’d love to host you! Mahalo, Dave & Neldie

Very Comfortable Kamaole Sands Condo Sleeps 4
Very comfortable end unit 1 bedroom condo 2 bathrooms (818 sq ft) with views of the pool, partial ocean view, remodeled kitchen and bathrooms, recently painted, new flooring in living room and conveniently located to everything you need, unit is airy and bright with extra windows. The kitchen is well stocked with all the essentials and cooking utensils. A 5 mins walk to the beach and 10-15 mins leisurely stroll to nearby shops and stores. I take my own photos for my unit.

Live, Love, Loft in Beautiful Maui
Experience the beautiful island of Maui and all its wonder in this modern loft in Central Kihei. You’re just minutes away from stunning beaches, local markets, and some of the best food on island. Nothing feels like you’ve arrived in Maui like the welcoming sand and warm waters of Charlie Young Beach, just across the street. Head down to The Cove to surf or paddle board with the locals. Or simply relax, put on a classic record and enjoy the sunset from the balcony.

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

Walk to Beach • FREE Paddleboard • Pools
Walk to the beach in minutes and enjoy a FREE paddleboard during your stay. This spacious Kihei condo features resort pools, beach gear, and a relaxed Maui vibe—perfect for couples or up to 4 guests 800 sq ft ground-floor condo just steps from the sand. Enjoy a pool, hot tub, and nearby pickleball courts. Watch whales (Dec–Apr) or kitesurfers from shore, with fast WiFi, AC, beach gear, parking, and on-site laundry.
Popular amenities for Kihei rentals with a pool
House rentals with a pool

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

Go for an Ocean Swim From a Fun Beach Villa

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

Oceanview Home with Private pool and hot tub

Maalaea Kai 307 - Maui Prime Oceanfront

Centrally located and steps to the beach!

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu
Condo rentals with a pool

A.R.A Retreats: The Townhouse

Renovated Condo | 3 Min Walk to Toes in the Sand!

Modern and Relaxing Oceanfront Vistas

Cozy Beach Condo Ocean & Mountain View’s

Penthouse Island Surf Shack -AC in BR & Living Room

BIG Ocean View, Hotel Zoned,3 minute walk to Kam 1

Remodeled Ground Floor| 3 mins walk to Kam I beach

Amazing views at Oceanfront Studio
Other vacation rentals with a pool

Kihei Maui Getaway

Luxurious Wailea Ocean Vistas

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

Ocean Front Vibes Maui

Maui Oceanfront Penthouse at Nani Kai Hale (609)

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

Top Floor Ocean Views | Beach & Restaurant Access

Recently Renovated - Iconic Ocean Views
When is the best time to visit Kihei?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $344 CAD | $366 CAD | $336 CAD | $283 CAD | $267 CAD | $267 CAD | $261 CAD | $245 CAD | $235 CAD | $243 CAD | $269 CAD | $321 CAD |
| 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 a pool in Kihei

Total vacation rentals
Explore 2,740 vacation rentals in Kihei

Nightly prices starting at
Kihei vacation rentals start at $123 CAD per night before taxes and fees

Verified guest reviews
Over 147,340 verified reviews to help you choose

Family-friendly vacation rentals
1,230 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
1,270 properties have a dedicated workspace

Wifi availability
2,720 of Kihei vacation rentals include wifi access

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

4.8 Average rating
Kihei stays are highly rated by guests—averaging 4.8 out of 5!
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- Maui
- Kamaole Beach Park II
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