
Holiday rentals with a pool in Kihei
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kihei
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Penthouse Island Surf Shack -AC in BR & Living Room
We were thrilled when this 6th floor penthouse condo in the heart of Kihei became available! It offered everything that we love about visiting Maui. It's across the street from a beginner surf break & next door to a surf school so we could walk outside our door, pick up surfboards and walk across the street to surf. It's a gorgeous walk to our FAVORITE beach, and next door to a variety of restaurants, shops and a grocery store. So we arrive, park, and have everything we love at our fingertips!

'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.

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.

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.

Stylish garden oasis next to 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. Soak in paradise on two lush garden patios!

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)

Full Ocean- Full Sunsets- Beaches at Royal Mauiian
Hawaii License: T-174-283-2640 Full ocean & beach front - all year sunsets. Royal Mauiian - Highly sought location in S. Kihei. Nicely done 1 BR - 1 BTH Nicely furnished, very streamlined open feel. Walk to restaurants, steps to Kam 1 beach, close to shops & activities. Rent a paddleboard, buy Hawaiian memorabilia, or shop at Harvest Moons - close by. Split Air in Bedroom & Living Area. Fully equipped kitchen. In Unit Laundry GET & TAT tax total of 18.5% included in final price.

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.

Ekahi Ocean Studio: Wailea Paradise by the 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.

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.
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

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

A201a-The closest Maui Banyan studio to the beach
Apartment rentals with a pool

Oceanfront Getaway, Brand New, Steps To Beach

Oceanfront Penthouse Vistas

Cozy Beach Condo Ocean & Mountain View’s

Modern Renovated Palms at Wailea Condo!

Spacious S. Kihei Suite New A/C across from Kam 3

ONLY $125/night June openings

Modern studio by the beach - Taxes included

Kihei Kai Nani ~ Building 6 Dream Location
Other holiday rentals with a pool

Kihei Oceanfront Condo - Steps to Beach & Surf

Ocean and beach view 1-bedroom condo

Kihei Maui Getaway

Modern Luxury Oceanview! Best views in complex!

Ma'alaea Surf Oceanfront 2 Bedroom Condo on 2nd Fr

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

Maui Kamaole A-206, Dramatic Ocean Views, Split AC

Maui Oceanfront Penthouse at Nani Kai Hale (609)
When is the best time to visit Kihei?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $323 SGD | $343 SGD | $315 SGD | $265 SGD | $250 SGD | $250 SGD | $245 SGD | $229 SGD | $220 SGD | $228 SGD | $252 SGD | $301 SGD |
| 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 holiday rentals with a pool in Kihei

Total holiday rentals
Explore 2,740 holiday rentals in Kihei

Nightly prices starting at
Kihei holiday rentals start at $115 SGD per night before taxes and fees

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

Family-friendly holiday rentals
1,230 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

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

Wifi availability
2,720 of Kihei holiday 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
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Polo Beach
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- Ka'anapali Golf Courses
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