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

Makani A Kai A5 beachfront, pool, a/c, w/d, 2 sups
Halerentals MAK A5 is a completely renovated beachfront condo, with high end materials throughout. RH furniture, cotton sheets, marble shower, gourmet kitchen, & a/c in every room-- just steps away from 3 miles of undeveloped beach! Bright spacious ground floor 1bed/1bath condo with fully stocked kitchen, and views of the beach, bay, & Haleakala volcano. King RH sofa bed in living room for up to 4 guests. Ideal for swimming, SUP, snorkeling, and surfing-- amazing value for families and couples.

â Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL
This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze ⊠soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! â Jump Start to The to the Road to Hana! â â New Cold Central AC â â Cliff Walk â â Ocean Viewâ â Private Hot Tub â â 44 ft Swimming Pool â King Bed â â Sunrise Viewâ â Star Gazingâ

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.

Spectacular views, prime location Kapalua, Maui.
Prime Kapalua location this stylish, romantic two-level villa offers elevated panoramic ocean views. Wake in a luxurious California King bed to stunning Pacific sunrises and fall asleep to the soothing sound of ocean waves. Relax on your private upstairs lanai or spacious patio and take in the breathtaking views. Walk to beaches, scenic trails and dining. Peaceful, magical- your perfect Maui escape. A/C on both levels and bright, airy interiors, this villa is a tranquil upscale Maui retreat.

NEWLY REMODELED OCEAN VIEW CONDO, STEPS FROM BEACH
Your next relaxing Lahaina escape awaits at this stunning 1-bedroom, 2-bath vacation rental condo - steps away from Kapalua Bay Beach & located next to The Resort at Kapalua Bay (formerly Montage). Your group of up to 6 guests will love returning to the comfort of this home, offering over 1,100 sq ft of living space. With easy access to championship golf courses, fine dining, walking/hiking paths, spas, & several bays/beaches for snorkeling, surfing, & relaxing, this is the perfect home base.

Oceanside 2-Bedroom 2-Bath Cottage, Stunning Views
Relax & enjoy stunning ocean & sunset views, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, two-story oceanfront cottage with a large covered lanai. This no-smoking cottage is located at the Kepuhi Beach Resort, close to pristine beaches, trails, and an oceanfront pool. The cottage is a peaceful place to work online, explore, or unplug & relax. You will enjoy blue ocean & beach views, colorful sunsets, breezes, tropical birds, waves, and whales in the winter.

Kula Jewel - Pool, Hot Tub & Awesome Views!
Pamela has been hosting two fully permitted listings for the last 11 years with over 1,000 five star reviews. BUT this one, Kula Jewel, burned to the ground in the Maui wildfires in 2023. We have recently completed building the NEW Jewel, and it is GORGEOUS! We just had our first guests stay, and this was their review: "Pamelaâs place is extraordinary! The views are stunning! The design and decor are fabulous in every detail! Iâve stayed in many Air B&Bs; I give her place my highest rating!"

Amazing Kapalua ,Stay 7 nights, only pay for 6 !
Our place is close to 3 beautiful beaches, 2 spectacular golf courses, tennis garden, hiking trails, whales, zip line, shops, restaurants, pools, barbecue, and spas. Youâll love our place because of the incredible views from the outdoor garden. It is huge and we call it our living room on the lawn. You'll love the ambiance, neighborhood, people. You will love everything about the Ridge at Kapalua. Our place is good for couples, solo adventurers, business travelers, not suitable for children.

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi
Locally Owned and Operated 1BD/2BA condo with the best direct beachfront location, panoramic Ocean views, sunsets, and seasonal whale watching. The ownerâs spared no expense in renovating this unit making it handâs down one of the nicest units in all of the Mahana. Wake up to the cool tropical breeze and sounds of the shoreline just 50 feet away. Floor to ceiling windows in the living area and bedroom bring the stunning views and warm Maui sun inside while central AC keeps you cool inside.

Ocean Front Paradise! Quiet Romantic!
THERES NO PLACE LIKE MAUI! OCEANFRONT condo greets you with endless ocean views, open floor plan and the feeling you have just arrived in Heaven! Step out onto the private lanai and you are captivated by the soothing sound of the waves, warm sunny breezes and turtles everywhere! You deserve the BEST and this home offers it! Located in a perfect location far from the maddening crowd yet walking distance to restaurants, shopping, nightlife, and sightseeing tours. APN2380140110057000

Whales Watch: Luxe Beachfront-180° Ocean views/AC!
Watch Whales breach during their migration and boats sailing by while snuggled up in your dreamy oceanfront bedroom kingsize bed with a cup of coffee! If you love the sound of the ocean, then this is the place for you. This luxuriously remodeled, secluded corner unit, Maui hideway is just 15 feet from the ocean with unbeatable, 180 degrees ocean views. Located on the 5th floor of Valley Isle Resort in Kahana (Within the Hotel Zone).

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
Popular amenities for Maui County rentals with a pool
House rentals with a pool

Relaxation in Kapalua-Specials!

Tranquility on West Moloka'i

Newly Remodeled Cottage

Go for an Ocean Swim From a Fun Beach Villa

Luxe 3BR Pualei Beach House Retreat

The Artists House

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

Aloha Aku Honu2 Suite â Relax by the Sea in Tranqu
Apartment rentals with a pool

Direct Waterfront, Air conditioned, Amazing Views!

Luxury Oceanfront Turtles Sunsets - Maui, Hawaii -

Full Ocean- Full Sunsets- Beaches at Royal Mauiian

Very Comfortable Kamaole Sands Condo Sleeps 4

Turtle Cove Oceanfront Views Island Sands Resort

Comfort and views near best beaches on Maui

Panoramic Views right on a Sandy Swimmable Beach

Boho Beach Retreat *OCEAN VIEWS*
Other holiday rentals with a pool

Ocean Views- Beachfront- Steps to a Sandy Beach!

Mahana 1215 Penthouse

Kihei Maui Getaway

Turtles & Tales: Luxe Beachfront w/AC & Ocean view

All New Beachy Chic Remodel, Ocean front with AC

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

Chasing Life On Maui - AC, Pool, Hot Tub

Oceanfront Lahaina Studio on the Sand 327
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Polo Beach
- Wailea Beach
- Kapalua Bay Beach
- Ka'anapali Golf Courses
- Maui Ocean Center
- Black Rock Beach
- Old Lahaina Luau
- Ulua Beach
- HÄmoa Beach
- Big Beach
- Maui Vista Condominium
- Whalers Village
- Black Sand Beach
- Haleakala National Park
- Peahi
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- Kihei Kai Nani
- Kahana Beach
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- Things to do United States
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