Vacation rentals with a pool in Napili Bay

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Top-rated rentals with a pool in Napili Bay

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Kihei

4.92 out of 5 average rating, 144 reviews

Beach Area Condo

Steps from the beach, restaurants, shopping, coffee, sunset views. Roomy condo with large sofa and king bed. Steps to the pool, sauna, and hot tub and grill area. Quiet, off the main street location, but easy walk to everything, even a health food store! AC, floor fan, and ceiling fans. Large kitchen, tile shower, stone floors in living areas, easy access to highway, or walk to the water's edge and enjoy! Free parking on site. GE116536524801 TE116536524801 Special for June,July, August

Guest favorite

Home in Kihei

4.96 out of 5 average rating, 409 reviews

Stunning ocean view, heated pool at home by Wailea

Last minute bookings 5 days before arrival, and week long stays are 10% off. 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

Guest favorite

Home in Kula

4.91 out of 5 average rating, 303 reviews

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela (owner/host) has been hosting two fully permitted listings for the last 10 years with over 1,000 five star reviews. BUT this one, Kula Jewel, burned to the ground in the Maui wildfires in August last year. We are in the process of rebuilding a GORGEOUS new home, and we are taking bookings for 2025, but we donʻt have photos yet. Iʻm including some photos of the STYLE of house we are building, but not the *actual* house. Ask about our special refund policy if we are not ready by Christmas!

Guest favorite

Condo in Kihei

4.89 out of 5 average rating, 123 reviews

Incomparable Maui Sunset condo, includes all taxes

This Renovated, beach themed condo in the Oceanside Maui Sunset is shaded from the afternoon sun on the B side. Our rate includes the 19% state tax! 2 full bathrooms, a new 75" TV, stove, dwasher quartz counters and new thick futon mattresses. The view from the lanai is over the resort's beautiful grounds (with largest private pool in Kihei) to the ocean. Good architecture and concrete construction keep units in this well managed complex private and safe. High speed internet (196Mbps).

Superhost

Condo in Kihei

4.83 out of 5 average rating, 143 reviews

Palms At Wailea #608-2 BR/2 BA. Oct./Nov Special

Beautiful Palms At Wailea Condo, located in the heart of Wailea surrounded by $mil.homes. 5* location.New Vinyl wood flooring & Split Air-system throughout.New outdoor dining set & LG dishwasher. Immaculately clean & comfortable. Walking distance to shops, hotels, restaurants, beaches.1200 sq. ft., 2BR/2Ba, wide open floor plan ,2nd. fl.unit. Very private. Large lanai with full size barbecue. Low rise complex with tiled pool & jacuzzi. Views from the Club House & Pool.The best place to stay!

Superhost

Condo in Kihei

4.82 out of 5 average rating, 261 reviews

Sea Views entire 1 Bedroom Apartment Poolside

Unobstructed sea views. Small 16 unit property with Pool outside your door. Remodeled 478 sf sunny and cozy apartment. Queen Bed in master, sofa bed in living room. Island Counter has 3 stools and serves as a computer table. Very convenient location in central Kihei. 3-4 Short blocks to restaurants, marketing, shopping and entertainment at the Triangle. Cove Beach across the street for water sports and surf lessons. Pet Deposit is $800 and refunded 30 days after checkout.

Superhost

Condo in Kihei

4.8 out of 5 average rating, 238 reviews

Adorable Romantic Studio

Sweetest studio in Maui. Cute little Queen bedroom with stunning mural, barn doors to bathroom. View of sunrise over Haleakala. Located across from the Cove and Kalama Park. Ideally situated for beaches, surfing, bars, restaurants and shopping all within easy walking distance. In-room fridge and coffee. Communal pool, grill and poolside dining area. Free parking lot behind the building. (GET and TAC taxes inc). Please note that there may be construction in the building 1/12-3/18.

Guest favorite

Condo in Lahaina

4.97 out of 5 average rating, 103 reviews

2024 Special! Ocean views! Updated+Air Conditioned

At last, you’ve found an extraordinary combination of secluded privacy, breath taking ocean views & magical sunsets. Our split Air Conditioned apartment has been beautifully updated and features a large private bedroom with a King size bed & a Queen sofa sleeper in the living room. The apartment has all new modern furniture, 700 count linens, granite counter tops & stainless steel appliances. Direct water access, 2 pools, hot tubs, Koi ponds, putting greens and more!

Superhost

Condo in Kaunakakai

4.71 out of 5 average rating, 167 reviews

*VEHICLE INCLUDED! Wavecrest Resort EAST MOLOKAI

TA-075-407-5648-01 THIS UNIT COMES WITH THE ABILITY TO USE OF AN SUV...... UPDATE!!!! We now have dedicated internet!!!!No more bad resort Wi-Fi!!! This unit is located on the island of Molokai. After years as a long term rental, my cozy,semi-private location at Wavecrest Resort is a vacation rental again. Often described as a home away from home this unit will bring a warm feeling to your heart and soul.

Guest favorite

Condo in Lahaina

4.98 out of 5 average rating, 170 reviews

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.

Superhost

Condo in Kihei

4.84 out of 5 average rating, 351 reviews

Cheap Cozy Studio- Very active legal vacation zone

Our place is close to the beach, family-friendly activities, Shops of Wailea, many Wailea Hotels: Andaz, Fairmont, Marriott Four Seasons Hotel, etc., restaurants, golf courses, tennis court. You’ll love my place because of the comfy bed, big TV, the views, overlooking pool and palm trees with easy access straight down to pool/jacuzzi/BBQ from your lanai. .

Guest favorite

Condo in Kihei

4.86 out of 5 average rating, 177 reviews

Studio w/Beach, Pool, Hot Tub, Tennis, & BBQ! 15A

Experience a tropical retreat in our newly renovated studio condo, infused with Hawaiian flair and located in a peaceful part of the complex. Just across the street from a sandy beach and ancient Hawaiian fishpond, it’s perfect for turtle spotting and enjoying stunning sunsets. Guests can relax with amenities such as a pool, hot tub, BBQ, and tennis court.