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

Total vacation rentals
Explore 350 vacation rentals in Lahaina

Nightly prices starting at
Lahaina vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 5,420 verified reviews to help you choose

Family-friendly vacation rentals
180 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
160 properties have a dedicated workspace

Wifi availability
340 of Lahaina vacation rentals include wifi 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.

Luxury Mahana Studio-Great Views-WiFi-Free Park
Locally Owned and Operated Studio 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. Located on North Kaanapali Beach. Enjoy stunning views and the warm Maui sun inside while central AC keeps you cool and comfortable any time of day.

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack
Escape and fall in love with “Ka Hale Aloha-The Love Shack” where paradise awaits you....This adventurous hideaway will leave you feeling refreshed, relaxed and more alive!! Experience all the life & Aloha the island of Maui has to offer in your private detached bungalow located on an old 8 acre fruit plantation turned condos, steps to the ocean & walking distance to 2 beaches. Ka Hale Aloha will make you feel like you’re truly living the island life. * Check us out on IG at @thoughtfulstays

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.

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.

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.

Ka'anapali Oceanfront Dream-view Retreat with AC!
This serene oceanfront retreat is located along the Kaanapali coast, less than 50' from the crashing waves. The unit offers a whole lot of Aloha, with unobstructed views of an expansive crystal blue/green ocean, swaying palm trees, adjacent islands, starry skies and sea life (sea turtles and monk seals all year long, migrating humpback whales from late Dec through April). The interior is clean, nicely appointed, & has lots of amenities to make your stay comfortable & enjoyable.

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.

Oceanfront Resort, Peaceful Mountain View Studio
Come stay at Lahaina Shores 506: - Oceanfront Building: Direct access to a sandy beach, pool, and hot tub just steps from the lobby - Mountain Views: Wake up to stunning sunrises from your 5th-floor lanai - Sunny & Clear: West Maui averages ~290 sunny days/year! - Amenities Nearby: Minutes drive to open spots like the Cannery Mall, Lahaina Gateway Center, & classic restaurants - West Maui: Only ~35 mins from the airport Note: Car recommended to explore the island

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

Absolute Beachfront with Million-Dollar Views!
My place is close to Kaanapali, Napili and Lahaina. The beach out front has gated access from only three resorts. You’ll love my place because of the view, the beach, and close proximity to Kaanapali, Kapalua, Napili, and all the beautiful scenery that West Maui has to offer. My place is good for couples, solo adventurers, and families (with kids).
Popular amenities for Lahaina rentals with a pool
House rentals with a pool

Relaxation in Kapalua-Specials!

Oceanfront Paradise with Pickleball gear!

Chic Villa 2 | Modern Vibes by the Ocean

Luxe 3BR Pualei Beach House Retreat

Stunning ocean view Villa, Heated pool, Wailea

Kula Jewel - Pool, Hot Tub & Awesome Views!

Studio Kaanapali Beach, Sleeps 3, Beach Cabana, Ja

Serene and Peaceful with Heated Pool
Condo rentals with a pool

Ocean Views- Beachfront- Steps to a Sandy Beach!

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

Beautiful Papakea 1 Bedroom with A/C

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

Luxury Vacationing Modern Condo Aug Specials $275

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

Whales Watch:180° Ocean views/Lux Remodel/Beach/AC

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

Kahana Ocean View Condo | Beach & Pool | King Bed

Maui Sunset View Ocean View Condo in Kaanapali, Hawaii

One of Our Best ~ Gorgeous Ocean Front!

Kapalua Ridge 1915- Platinum Ocean View Villa

Napili Point A6 | Cozy Oceanfront 1BR Retreat

Rooftop at Lahaina Roads

223 Island Delight, This Condo Is Calling Your Nam

Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt
When is the best time to visit Lahaina?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $491 CAD | $480 CAD | $418 CAD | $1,106 CAD | $1,124 CAD | $1,060 CAD | $977 CAD | $766 CAD | $507 CAD | $470 CAD | $526 CAD | $507 CAD |
| 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 |
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- Maui
- Kaanapali Beach
- Lahaina Beach
- Wailea Beach
- Polo Beach
- Honolua Bay
- Kapalua Bay Beach
- Maui Vista Condominium
- Kepuhi Beach
- Big Beach
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- Haleakala National Park
- Kihei Kai Nani
- Kamaole Beach Park II
- Maui Ocean Center
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- PacWhale Eco-Adventures
- Aston Mahana at Kaanapali
- Peahi
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- Kamaole Beach Park III
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