
Vacation rentals with a pool in Kihei
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Kihei

Total vacation rentals
Explore 2,900 vacation rentals in Kihei

Nightly prices starting at
Kihei vacation rentals start at €77 per night before taxes and fees

Verified guest reviews
Over 150,680 verified reviews to help you choose

Family-friendly vacation rentals
1,280 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
1,310 properties have a dedicated workspace

Wi-Fi availability
2,860 of Kihei vacation rentals include wi-fi 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!
Top-rated rentals with a pool in Kihei
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

Family Oceanview | Beach Gear + Beach Access
Make family memories in this top-floor ocean-view condo in Kihei. Enjoy Pacific views, ocean breezes, year-round sunsets, and seasonal whale watching from the private lanai. Just steps away, the beach across the street is ideal for morning walks, beachcombing, dipping your feet in the water, and sunset strolls. The shallow, rocky shoreline is not ideal for swimming, but some of South Maui’s favorite swimming beaches are just a short drive away. A comfortable home base for Maui adventures nearby.

Mana Kai Palms Oceanfront Condo: Keawakapu Beach
Welcome to Mana Kai Palms Our luxurious, newly renovated condominium is located on Keawakapu Beach, named Maui's best for its pristine sand, clear waters, and abundant marine life. The Mana Kai Resort offers a wide range of amenities and with only 100 units, provides a warm, family feel. We are conveniently located minutes from all South Maui has to offer. Hosted by Tracy O'Reilly, a Superhost and #1 rated rental agent on Maui. Do as much as you want or as little as you desire at Mana Kai Palms

Groovy bright condo 2 bed / 2 bath South Kihei
Enjoy our home away from home! Bright Groovy Beach Condo offers you a naturally lit and engaging space to relax with two bedrooms each with their own en suite bathrooms (4th bed is the pull out sofa bed in the living room). Enjoy your morning coffee on the lanai and listen to the birds. Haleakala Shores is located 300 meters from world famous Kamaole Beach III. You are also located within a casual stroll (or snorkel or paddle board) north to Kamaole Beach II, I and finally Charley Young Beach.

Lovely Oceanfront Condo with pool
Discover Paradise: Lovely Oceanfront Condo with Pool & Unforgettable Views Wake up to the symphony of waves and endless blue horizons in this stunning oceanfront condo, your ideal escape for relaxation, romance, or family adventures. Nestled right on the edge of the beach, this beautifully appointed retreat offers breathtaking panoramic ocean views from your private balcony—perfect for sipping morning coffee as the sun rises over the water or unwinding with a glass of wine at sunset.

Spacious 2BR + Private Alcove @ Maui Sunset, AC
Welcome to Maui Sunset in beautiful Kihei, Maui! Our spacious 2 Bedroom (plus extra bonus room), 2 Bathroom condo comes with full kitchen, air conditioning, washer dryer, and kid-friendly extras like a Pack ’n Play. Rare bonus room adds extra space for groups. Great location and steps to the beach. Enjoy the pool, hot tub, tennis, fitness gym, BBQs, and free parking. Elevator and stair access to our 2nd floor unit. Easy beach access and excellent value for your Maui stay in Kihei.

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.

Kihei Condo: Steps from Beach & Yummy Eats!
✨ Your Maui Escape Awaits! 🌺 Nestled in the heart of Kihei, our condo is just steps from Kamaole Beach Park—famous for golden sands, calm waters, and stunning sunsets. Stroll to local shops, food trucks, and restaurants, or unwind on your private lanai in true island comfort. With a central location near Haleakalā, the Road to Hana, and Twin Falls (waterfalls), this tranquil retreat is the perfect home base to savor all of Maui’s beauty, flavor, and adventure. 🌴☀️

Oceanfront Condo on magic Sugar Beach - Ocean View
•EAST/SOUTH MAUI IS OPEN FOR BUSINESS AND WELCOMING TOURISM• Life is sweet on Sugar Beach. Our oceanfront condo is fewer than 100 steps to a world-class beach that stretches for 5 miles. The smooth sand, gentle waves, and warm water create the ideal swimming experience. And when you are ready to come in, you can relax on our private beachfront lawn with your own lounge chair, table, and umbrella. Or maybe you prefer the pool? It’s perfectly maintained and private.

Upscale Oceanfront Penthouse Vistas
Full remodel and decorated ourfitted with all new furnishings. This elegant 2-bedroom, 2-bath condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei at Menehune Shores resort, all of Maui is within reach. Beach chairs, umbrellas, towels, and a cooler are all provided. We offer a fully stocked kitchen for those who want to cook. Experience the resort's many amenities such as beach access with snorkeling, a private pool, and grills.

Walk To Sand Beach, 2BR/2BA, Cozy Condo for Family
Enjoy your stay at our 2BA/2BR condo in Maui’s desirable S. Kihei. This our family's lifetime vacation home and we love the convenience & perfect location of this uint. Within the walking distance (~5 minutes) to Kihei's famous Charley Young Beach and Kamaole I Beach, you're free to enjoy the beach. Not to mention the unit is also close to bunch of local stores, restaurants in S.Kihei, Kihei Cafe, Coconut's Fish Cafe, Surf school and more for you to explore

3BR spacious Condo with Ocean View in top location
Enjoy ocean views and island living from this spacious 1,400 sq ft 3-bed/2-bath condo in the heart of Kihei. Located directly across the street from the beach, you can watch whales from the lanai or relax by the pool and BBQ area. Shores of Maui offers easy access to Kihei’s best beaches, shops, and restaurants, all within minutes. A perfect home base for families and groups looking for comfort, convenience, and the South Maui lifestyle.
Popular amenities for Kihei rentals with a pool
House rentals with a pool

Condo in Kihei 2 BR - 2 bath Condo

Stunning ocean view Villa, Heated pool, Wailea

Maui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool

Go for an Ocean Swim From a Fun Beach Villa

Kihei 533- OceanView, 5 min drive to stores/food

Oceanview Home with Private pool and hot tub

Oceanfront Stunner w/ Cruiser Bikes & Pickleball

Stunning One Bd Partial ocean, AC, wifi,Pool C209
Condo rentals with a pool

15 Steps to Beach! 2 Bedroom w/XL Kitchen & Pool!

Ocean View · King & Queen · Pool & Jacuzzi

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Spacious comfy unit Netflix & huge pool Maui Hill

Live, Love, Loft in Beautiful Maui

Premier Ocean Front unit 519 Guaranteed Hotel Zone

Coastal Dream Oceanfront Condo!

Romantic, Luxury Retreat w/Ocean View-Couples Only
Other vacation rentals with a pool

Newly Remodeled Ocean View Condo

NEW Ocean View 1 Bedroom Condo with Common Hot Tub

Stunning Ocean Views - September Specials $189

Sugar Beach Renovated 10% Discnt on 7 days Booking

Ocean Front Vibes Maui

King Bed + Pools | Steps to Kamaole Beach

Penthouse: Ocean View - Right on the Beach!

Stylish Kihei Condo in Oceanfront Resort Complex
When is the best time to visit Kihei?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €214 | €227 | €202 | €181 | €170 | €172 | €164 | €154 | €148 | €153 | €169 | €202 |
| 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 |
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