Holiday rentals with a pool in Kihei

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.

Location · Value · Outdoor spaces

Lovely Ocean View condo in Maui Vista Resort Kihei

This comfortable condo at Maui Vista Resort with a view of the ocean off in the distance has a tropical view facing toward the west. It is renovated with cool tiled flooring, granite countertops in the kitchen and bath areas, king bed, leather sofabed couch, with a sleek style. You'll love the open feel of this space and you'll have a great time being within easy walking distance of gorgeous beaches, delicious restaurants, lively bars, vibrant shopping, mesmerzing sunsets, and fun activities!

Location · Family · Grill

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.

Location · Family · Walkability

Beautiful Studio Condo with Partial Ocean View

This second-floor ocean view studio has everything you need to feel at home: Fully equipped kitchenette, dining area, comfy queen bed, cozy sitting area, SmartTV with streaming apps, Wifi, bathroom with bathtub, beach equipment, and much more. Resort amenities include a coin/card operated laundry room, pool, hot tub and tennis court. Less than 1 mile from shopping and restaurants. Enjoy stunning sunset views from the lanai or cross the street to Kalepolepo Beach to be with the sea turtles.

Location · Value · Parks

NEW Ocean View 1 Bedroom Condo with Common Hot Tub

Designed as our personal 2nd home, this beautifully furnished and decorated condo features high-end appliances. Your 5th-floor unit offers an unobstructed ocean view—no sidewalks, power lines, or parking lots in sight. Enjoy tennis, pickleball, pool, BBQ area, putting green, hot tub, and direct beach access—just steps away! The free parking lot is out-of-eyesight. 17.5% TA Tax is included. Sunsets are magical from your lanai. Both your living room & bedroom boast breathtaking ocean views.

Family · Value · Indoor spaces

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.

Value · Location · Nearby

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.

Family · Location · Air conditioning

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. 🌴☀️

Value · Family · Pool

Walk to Beach XL 1 Bedroom w/Pool & Jacuzzi

This is your perfect getaway place right across the beach! 1 b1 b condo includes fully set up kitchen, dining area and living room, Cal King size bed, full size washer and dryer in the unit(+laundry detergent), TV, beach chairs and cooler, wifi internet, shared jacuzzi and pool. Located in North Kihei across the street from Kalepolepo Beach Park and Turtle Sanctuary. 5 minute drive to stores and shopping. Building is secluded from the road and traffic.

Family · Location · Decor

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.

Location · Family · Access

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.

Family · Location · Check-in

Kihei Akahi C304-Newly Remodeled-Well Equipped-AC

Book with confidence this brand new remodeled, 1 bedroom, 1 bathroom (655 sq. ft) condo that provides an exceptional vacation experience. The condo offers tremendous value with it's beautiful level of finishes, and location. PMI Maui manages many units in South Maui. Please let us know if you are interested in any of our units and we will send you the Airbnb link to view all of our listings and reviews.

Value · Family · Laundry