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

Total holiday rentals
Explore 340 holiday rentals in Lahaina

Nightly prices starting at
Lahaina holiday rentals start at $35 NZD per night before taxes and fees

Verified guest reviews
Over 5,000 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wi-Fi availability
330 of Lahaina holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Lahaina rentals

4.8 Average rating
Lahaina stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Lahaina
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Ocean Views- Beachfront- Steps to a Sandy Beach!
Views! Views! Views! From the moment you enter Valley Isle unit 110 you will be mesmerized with ocean views from every room. This corner unit is located on the 1st floor and has direct access, steps to a sandy beach. Watch rainbows, turtles or whales from the spacious Lanai, a comfortable scenic space where you can spend your mornings, days or evenings, located within 15 feet from the ocean. Bedroom sliding door opens to tranquil sound of the ocean, doz-off with open doors to the sound of waves.

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.

Best Papakea Oceanfront *No resort fees* Unit A106
Relax at my ground floor direct oceanfront studio condo with stunning ocean views facing the island of Molokai and Lanai. Papakea Resort is located at North Kaanapali Beach and features 13 acres of lush landscaped grounds, fresh water Koi ponds, 2 swimming pools, 2 large jacuzzi's, 12 gas BBQ's, 2 putting greens, 2 shuffleboard courts and 3 tennis courts. ** PLEASE NOTE** that your quoted price includes the Hawaii State and Maui County TAT tax and GED taxes totaling 18.5%. No resort fees!!

Kula Jewel - Pool, Hot Tub & Awesome Views!
Pamela has been hosting two fully permitted listings for the last 12 years with over 1,500 five star reviews. BUT 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: "The Jewel is extraordinary! The views are stunning! I’ve stayed in many Air B&Bs. I give her place my highest rating!" Btw, we have not raised our prices. The service fee now shows.

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. You’ll 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.

Kaanapali Cottage ICC 29 Indoor/Outdoor Living
International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

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 owner’s spared no expense in renovating this unit making it hand’s 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.

Maui Full Oceanfront Paradise
Indulge in the ultimate Maui getaway at our full oceanfront condo. The cozy balcony beckons you to unwind and marvel at the mesmerizing sea life. Sip on your morning coffee, or relish a sunset cocktail while you watch the ocean's playful inhabitants. For those warm tropical nights, rest easy knowing that the condo is equipped with air conditioning to ensure a comfortable night's sleep. The fully stocked kitchen provides all the essentials for cooking up a delightful island feast.

Napili Bay Oceanview Resort Hideaway
Welcome to Napili Bay, Maui's hidden gem, and a favorite spot for some of the best snorkeling on Maui. Relax in the ocean breeze from your private lanai. Enjoy ocean views throughout the condo. Lush tropical landscaping, plumerias, monkeypods, and many more plant varieties throughout the property. 2nd floor studio condo, beautiful vaulted ceilings, low density property, old school Hawaiian resort. Easy access to world-class beaches, restaurants, shopping and golfing.

Kapalua, luxe, ocean view, beach, spa, golf/tennis
KAPALUA - Best location! Welcome to the luxuriously Kapalua Bay Villa #37B1. Bright and airy, with comfortable furniture and modern appliances. Scenic ocean view, a 5-minute walk to Kapalua Bay, Montage Resort, tennis, golf, hiking, zip-lining, amazing restaurants, and a first-class spa. Kapalua Bay Villas is a low-density community within the Kapalua Resort—a 15-minute drive to Kaanapali, and a 40-minute drive to Central Maui to explore the island.

Stylish Love Hideaway, Maui Kaanapali Oceanfront
Oceanfront studio in one of a kind boutique condominium, on world famous Kaanapali Beach. Wake up to a breathtaking oceanview, take it all in from spacious lanai, fall asleep to the sound of the ocean every night Located on the 3rd floor with close touch to ocean breeze and fantastic views, easy access to world-class beaches, restaurants, shopping and golfing

Kaanapali Fairway Villa 3BR/3BA.
Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.
Popular amenities for Lahaina rentals with a pool
House rentals with a pool

Relaxation in Kapalua-Specials!

Oceanfront Paradise with Pickleball gear!

Newly Remodeled Cottage

Go for an Ocean Swim From a Fun Beach Villa

Luxe 3BR Pualei Beach House Retreat

Stunning ocean view Villa, Heated pool, Wailea

Studio Kaanapali Beach, Sleeps 3, Beach Cabana, Ja

Aloha Oceanfront Retreat 327
Condo rentals with a pool

Luxury Oceanfront Turtles Sunsets - Maui, Hawaii -

Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba

Stunning Panoramic Oceanfront 2 Bed Bath with AC

Mahana 1015 - Luxury Oceanfront Condo (1bd/2ba)

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

Whales Watch Beachfront Oasis, 180° Ocean views/AC

Oceanfront Resort, Peaceful Mountain View Studio

Kaanapali Fairway Vista - Legal STR Hotel Zoned
Other holiday rentals with a pool

58-4 Puamana, Views, Views, INCREDIBLE Views!!

Spectacular views, prime location Kapalua, Maui.

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack

One of Our Best ~ Gorgeous Ocean Front!

Rooftop at Lahaina Roads

Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt

Lanai life like on a Boat Deck. Ocean front lux!

Beachfront Surf Hale Puamana 272-4
When is the best time to visit Lahaina?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $608 NZD | $594 NZD | $517 NZD | $1,368 NZD | $1,390 NZD | $1,311 NZD | $1,208 NZD | $948 NZD | $627 NZD | $582 NZD | $651 NZD | $627 NZD |
| Avg. temp | 23°C | 23°C | 23°C | 24°C | 25°C | 26°C | 27°C | 27°C | 27°C | 26°C | 25°C | 24°C |
Destinations to explore
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- Maui
- Kaanapali Beach
- Lahaina Beach
- Whalers Village
- Wailea Beach
- Polo Beach
- Kapalua Bay Beach
- Honolua Bay
- Maui Vista Condominium
- Kepuhi Beach
- Big Beach
- Old Lahaina Luau
- Black Rock Beach
- Haleakala National Park
- Black Sand Beach
- Ka'anapali Golf Courses
- Kihei Kai Nani
- Kamaole Beach Park II
- Maui Ocean Center
- KOA Resort
- Hāmoa Beach
- Maui Arts & Cultural Center
- PacWhale Eco-Adventures
- Peahi
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