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

180* Oceanfront View w/ AC! Remodel+2Pools+Clean
We are a LEGAL Short Term Rental. If STRs are banned, we will refund your reservation money. We are 6 miles north of the fire. Our beaches, sunsets & ocean are still amazing. Remodeled Large Studio w/ AC. Sleep 30' from the ocean to the sound of waves! PANORAMIC VIEWS/SUNSETS! 2 Relaxing Oceanside POOLS & hot tub. Fully-equipped kitchen. Walk-in rain shower. GREAT LOCATION! Close to Kaanapali, Kapalua, groceries, restaurants, beaches. TURTLES love this area. Free Parking. No Resort Fees.

Ka'anapali Oceanfront Dream-view Retreat with AC!
This serene oceanfront retreat is located along the Kaanapali coast, less than 50' from the beach and waves. The unit offers a whole lot of Aloha, with unobstructed views of an expansive crystal blue/green ocean, crashing waves, 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.

Lahaina Studio: Beachfront, Mountain View, Hot Tub
Pineapple Lahaina Studio invites you to experience a tranquil Maui retreat in the heart of Lahaina. Nestled within a quiet rebuilding enclave, our bright, fully‑equipped studio offers modern comforts: king bed, kitchen, AC, and our resort pool and hot tub. Step outside to abundant nature: native trees, flowers, birds, and gentle ocean breezes. A quick drive brings you to vibrant dining, shopping, and the historic Old Lahaina Luau. Ideal for travelers craving peace and access to Maui’s culture.

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 & centrally located next to the Montage Resort. 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, shopping, spas, & several bays/beaches great 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.

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.

Ka Hale Aloha (The 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 than ever before!! 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, just steps from the ocean. This is a unique experience...there’s nothing quite like "Ka Hale Aloha" on island * Check us out on IG at @kahalealoha

3-min Walk to Beach, Modern & Fun Condo
- Walk across the street to beautiful, uncrowded Kahana Beach - Beach Bag, Beach Towels, Beach Chairs and Umbrella Included Free - See sea turtles and monk seals swimming in the ocean - 8 minute drive to Ka'anapali and Kapalua golf courses - Arcade machine with classic 80's games - Drop down bar on the lanai - A/C in the bedroom and living room - King size bed and queen sleeper sofa - Cable TV and smart TV, WiFi stereo - Walk to nearby groceries, restaurants, and bars - Fast WiFi

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.

Beachfront Designer Remodel/AC, 180⁰ Ocean View
Watch the Whales breach during their migration and boats sailing by while sitting up in your dreamy oceanfront bedroom with a cup of coffee! If you love the sound of the ocean, then this is the place for you. Luxuriously remodeled Island Oasis, just 15 feet from the ocean with unbeatable, 180 degrees ocean views. Super private, secluded corner unit located on the 5th floor of Valley Isle Resort in Kahana. Inside the Hotel Zone.

DIRECT OCEAN FRONT STUDIO W OCEAN IS UR BACK YARD!
This is a hotel-zoned condo. It will not be affected by potential upcoming county regulations. Book with confidence!! Thank you for considering my direct ocean front studio condo in Kahana, my condo is located minutes outside of Lahaina , Kaanapali , Napili and Kapalua. You'll find the ocean view from my lanai/ room to be breathtaking and serene. This is truly an hidden gem on Maui.

Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt
Spectacular Ocean & Outer Island views from your Air Conditioned condo! Enjoy snorkeling with Sea Turtles in your backyard, seasonal Whale Watching from your kitchen, and breathtaking Sunsets... Welcome to Paradise! Traveling with family or friends? Please see our other listing just few doors down: Oceanfront Oasis! Sea Turtle Cove B17 Napili Point
Popular amenities for Lahaina rentals with a pool
House rentals with a pool

Mahalo Pono @ Ka'anapali Royal

Newly Remodeled Cottage

Oceanview Home with Private pool and hot tub

3BR/3BA Pualei Beach House

Wake Up to Sweeping Ocean Views in Platinum Style

Stunning ocean view, heated pool at home by Wailea

Kula Jewel - Pool, Hot Tub & Awesome Views!

Bungalow walk to beach + Pickleball gear and Bikes
Apartment rentals with a pool

Direct Waterfront, Air conditioned, Amazing Views!

Luxury Oceanfront Turtles Sunsets - Maui, Hawaii -

Napili Nani cottage for 2 w/AC ~ *Renovated*

Beautiful Papakea 1 Bedroom with A/C

Oceanfront Bliss (direct ocean view) Maui.

Beautiful Ocean View on Quiet Side of Honua Kai!

Kaanapali Fairway Vista - Legal STR Hotel Zoned

Ocean's Edge Romance: Sunsets, Whales, Views!
Other holiday rentals with a pool

Maui Beach Frt Condo w/ AC Kaanapali Shores Resort

Stunning Panoramic Oceanfront 2 Bed Bath with AC

Oceanfront penthouse - stunning view!

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

Royal Kahana+WasherDryer in Unit +Kitchen+AC

Gorgeous Kapalua Home with Views

New Remodel Oceanfront Sunset Paradise

Stunning Maui Villa
Quick stats about holiday rentals with a pool in Lahaina
Total rentals
280 properties
Nightly prices starting at
€ 69 before taxes and fees
Total number of reviews
4.4K reviews
Family-friendly rentals
160 properties are a good fit for families
Rentals with dedicated workspaces
120 properties have a dedicated workspace
Wifi availability
270 properties include access to wifi
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- Maui
- Kaanapali Beach
- Kahului Beach
- Kepuhi Beach
- Lahaina Beach
- Honolua Bay
- Sandy Beach
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- Spreckelsville Beach
- Olowalu Beach
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