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

Total holiday rentals
Explore 2,900 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 150,680 verified reviews to help you choose

Family-friendly holiday rentals
1,280 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

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

Wifi availability
2,860 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!
Top-rated rentals with a pool in Kihei
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

The Whale Watch 208-Oceanfront Kihei
HOTEL ZONED, NOT affected by new Hawai’i legislation banning 1/2 of Maui’s Airbnbs Next to Pacific Whale Sanctuary, this newly renovated 2bed, 2bath is a modern oceanfront oasis. On the 2nd floor, overlooking a heated pool with sweeping ocean, sunset, and mountain views. Steps away to a protected ancient Hawaiian beach perfect for snorkeling, viewing sea turtles and whales shopping, dining and sightseeing just moments away. Sip cocktails or grill out on the rooftop deck with 360* views of Maui.
4.88 out of 5 average rating, 139 reviews
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
4.97 out of 5 average rating, 106 reviews
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.
4.93 out of 5 average rating, 206 reviews
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.
4.98 out of 5 average rating, 125 reviews
Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
Mana Kai 608 is a remodeled oceanfront condo DIRECTLY ON Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, on the border of Wailea and Kihei. Our condo is designed with a modern surf feel in mind, welcome to the beach! If you enjoy Wailea's 5 star resorts right down the beach, but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best PM in Maui, Tracy O'Reilly to take amazing care of you!
4.99 out of 5 average rating, 232 reviews
STUNNING Unobstructed Ocean View*Beachy Condo!
This inviting 602-square-foot retreat features an expansive lanai with breathtaking, unobstructed views of the Pacific Ocean. The open-concept layout creates a bright, airy atmosphere complemented by coastal décor that captures the essence of island living. Enjoy restful nights in the comfortable king bed, and extra space with a queen-size sleeper sofa for additional guests. Every detail is thoughtfully designed to offer a relaxing, beach-inspired escape with all the comforts of home.
4.89 out of 5 average rating, 237 reviews
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.
4.9 out of 5 average rating, 177 reviews
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.
4.99 out of 5 average rating, 151 reviews
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. 🌴☀️
4.85 out of 5 average rating, 153 reviews
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.
4.93 out of 5 average rating, 221 reviews
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.
4.92 out of 5 average rating, 197 reviews
Oceanfront Mana Kai Penthouse..Heaven meets Earth!
Wake up to breathtaking, panoramic north-to-south ocean views from the Mana Kai’s top-floor penthouse level, just steps from Keawakapu Beach—2.75 miles of Wailea’s longest sandy shoreline at your door. Snorkel, swim, paddleboard, body surf, or watch whales from your private 200 sq. ft. lanai. This spacious 2-bedroom, 2-bath oceanfront suite sleeps four, with two king beds and a beautifully updated private bathroom for each bedroom.
4.96 out of 5 average rating, 143 reviewsPopular amenities for Kihei rentals with a pool
House rentals with a pool

Condo in Kihei 2 BR - 2 bath Condo
4.88 out of 5 average rating, 119 reviews
Stunning ocean view Villa, Heated pool, Wailea
4.96 out of 5 average rating, 469 reviews
Go for an Ocean Swim From a Fun Beach Villa
4.92 out of 5 average rating, 153 reviews
Aloha Aku Bamboo Suite – Discover Beachfront Seren
4.98 out of 5 average rating, 45 reviews
Oceanview Home with Private pool and hot tub
4.94 out of 5 average rating, 50 reviews
Stunning One Bd Partial ocean, AC, wifi,Pool C209
4.98 out of 5 average rating, 47 reviews
Oceanfront Stunner w/ Cruiser Bikes & Pickleball
4.74 out of 5 average rating, 128 reviews
Kihei 533- OceanView, 5 min drive to stores/food
4.75 out of 5 average rating, 55 reviewsApartment rentals with a pool

Fun Updated Ocean View Condo at Maui Vista Resort
4.91 out of 5 average rating, 328 reviews
Beautiful Studio Condo with Partial Ocean View
4.91 out of 5 average rating, 170 reviews
Ocean View Superior Deluxe - 200
4.84 out of 5 average rating, 432 reviews
King Bed + Pools | Steps to Kamaole Beach
4.96 out of 5 average rating, 238 reviews
Walk To Sand Beach, 2BR/2BA, Cozy Condo for Family
4.89 out of 5 average rating, 190 reviews
Island Surf #206 Your South Maui Gem is here
4.88 out of 5 average rating, 234 reviews
15 Steps to Beach! 2 Bedroom w/XL Kitchen & Pool!
4.86 out of 5 average rating, 343 reviews
Amazing views at Oceanfront Studio
4.85 out of 5 average rating, 572 reviewsOther holiday rentals with a pool

Family Oceanview | Pool + Hot Tub | Private Lanai
4.89 out of 5 average rating, 213 reviews
"Dancing Turtle's "Guest Suite"
4.97 out of 5 average rating, 428 reviews
Romantic, Luxury Retreat w/Ocean View-Couples Only
4.99 out of 5 average rating, 199 reviews
Ocean Front With Ocean View! AC, King Bed, 2 Bath!
4.93 out of 5 average rating, 163 reviews
Maui is Open - Come Support the Locals
4.98 out of 5 average rating, 120 reviews
Stylish Kihei Condo in Oceanfront Resort Complex
4.99 out of 5 average rating, 147 reviews
Fully remodeled, Ocean View, 3 mins walk to beach
4.96 out of 5 average rating, 248 reviews
2 Bed/2 Bath Modern & Elegant Oceanfront Vistas
4.94 out of 5 average rating, 157 reviewsWhen is the best time to visit Kihei?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $318 SGD | $337 SGD | $300 SGD | $269 SGD | $253 SGD | $255 SGD | $244 SGD | $228 SGD | $219 SGD | $227 SGD | $251 SGD | $300 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 |
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