
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 G$4,174 GYD 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 & kid-friendly amenities

Rentals with dedicated workspaces
160 properties have a dedicated workspace

Wi-Fi availability
340 of Lahaina vacation 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.

A.R.A Retreats: The Molokini
FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

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

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.

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.

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.

Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba
A legal short term rental! 1 bedroom, 1 bath with open floor plan. This condominium has a comfortable Cal-King bed in the bedroom and sofa sleeper in the living-room. **Central A/C*Fully equipped kitchen w/ granite counters*refrigerator*stove top + oven*coffee maker* microwave* dishwasher* washer/dryer* Free in room WiFi** Onsite gym is managed by an outside contractor and charges $9/day for useage.

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!

Oceanview Townhome • Modern • 2 Min Walk to Beach!

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

Maui direct ocean front . Super private
Condo rentals with a pool

Ocean Views- Beachfront- Steps to a Sandy Beach!

Fresh Reno on 8th Floor Studio - Amazing Views

Beautiful Papakea 1 Bedroom with A/C

Soothing Waves with 180° View In Kahana, HI

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

Oceanview Lanai, Pool, Hot Tub, Across the Beach

Luxury condo • 180° Ocean Views • Steps to Beach

Oceanview Maui Condo, Turtles, Whales, Rainbows
Other vacation rentals with a pool

Guest Favorite: Beachfront AC, Seals, Honu & Surf

Romantic Oceanfront Escape | Panoramic Views

Island Views Oceanfront 2 Master Bedrooms, Cold AC

Kahana West Maui Beach Condo | Ocean Views & Pool

Maui Sunset View Ocean View Condo in Kaanapali, Hawaii

LahainaShoresBeachfrontPanoramic Endless OceanView

87-1 Escape to Paradise at Puamana's Hale Nalu

Rooftop at Lahaina Roads
When is the best time to visit Lahaina?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$73,044 GYD | G$71,375 GYD | G$62,192 GYD | G$62,401 GYD | G$62,401 GYD | G$62,401 GYD | G$145,254 GYD | G$113,949 GYD | G$75,340 GYD | G$69,914 GYD | G$78,262 GYD | G$75,340 GYD |
| 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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