• Vacation Rentals
    • California
    • Hawai’i
    • Washington
    • Dominican Republic
    • Stay for the Holidays
    • Free Night Promotion
  • Experiences
  • Vacation Rental Management
  • About Gather
    • Meet the Team
    • Our Property Managers
    • Blog
    • FAQ
    • Terms & Conditions
    • Privacy
    • Contact Us
  • Vacation Rentals
    • California
      • Del Mar
      • La Jolla
      • Rancho Santa Fe
      • San Diego Area
      • Napa Valley Area
    • Hawai’i
      • Big Island
      • Kauai
      • Maui
      • Oahu
      • Resorts
    • Washington
      • Bellingham
      • Birch Bay
    • Dominican Republic
      • Casa de Campo
    • Stay for the Holidays
    • Free Night Promotion
  • Experiences
  • Vacation Rental Management
  • About Gather
    • Meet the Team
    • Our Property Managers
    • Blog
    • FAQ
    • Terms & Conditions
    • Privacy
    • Contact Us
  • 877-692-1050

Learn more about vacation rental property management by Gather.


Jeremy Stice

Clear dates

Duration

Starting Month

October

November

December

January

February

March

Adults

Ages 18 or above

Children

Ages 2-17

Infants

Under 2

Pets

Bringing your pets?

Where to?

Search For

When

Who

Adults

Ages 18 or above

Children

Ages 2-17

Infants

Under 2

Pets

Bringing your pets?

Filters

Price range

The average night price is $383

$
$

Rooms

Baths

Property Type

Amenities

Page 1 of 3

    Relax on the spacious lanai, where plush seating and panoramic ocean views create the perfect spot for morning coffee or evening sunsets. Unwind on the lanai while soaking in the breathtaking ocean views, offering the perfect setting for relaxation and tranquility. The open-concept living area blends modern luxury with island charm, offering expansive ocean views through wide sliding doors. The plush sectional sofa and sleek kitchen with high-end appliances create an inviting space. The gourmet kitchen is a chef's dream, featuring a large central island with seating, top-of-the-line appliances, and rich wood cabinetry. The open design allows you to enjoy stunning ocean views while preparing meals, with elegant pendant lighting. The resort-style pool is a true tropical oasis, surrounded by lush greenery and dramatic rock formations. The tranquil waters feature cascading waterfalls, creating a serene ambiance. The primary suite offers a serene retreat with direct access to the lanai and breathtaking ocean views. The king-sized bed is complemented by luxurious linens and tasteful decor, creating a peaceful atmosphere for rest and relaxation. Relax on the plush sofa while soaking in uninterrupted views of the ocean, creating a seamless connection between indoor comfort and outdoor serenity.
(2)

Wailea Luxury Residence Hoolei 23-3

3 Beds
3.5 Baths
6 Sleeps

Starting at $817/night

    This resort-style pool features waterfalls, lounge chairs in the water, and a serene tropical setting perfect for relaxation. This open-concept living area offers seamless indoor-outdoor living with a spacious sectional and views of the lush surroundings. Open kitchen with granite island, cozy living area with TV, and a lanai offering tropical views. Step into a seamless blend of indoor comfort and outdoor relaxation on the lanai space, perfect for lounging or entertaining. Relax by the tropical pool and hot tub, surrounded by lush palms and serene landscaping. Perfect for unwinding in paradise. Spacious living area with a plush sectional sofa, modern ceiling fan, and open layout that flows into the kitchen, creating a perfect spot for relaxation and gathering. Dine in the elegant dining area with table for eight.

Wailea Luxury Residence Hoolei 93-3

3 Beds
3.5 Baths
8 Sleeps

Starting at $737/night

    Take in the breathtaking panoramic ocean views from your private lanai, the perfect spot to enjoy its beauty Spacious open-concept living area with stunning ocean views and modern décor. Enjoy your morning coffee on the private lanai. Welcome to Mahana 1119, your tropical home away from home! Welcome to Mahana 1119! Dining area with open-concept design and panoramic views of the ocean. The living area offers plush sectional sofa and open floorplan to the kitchen for seamless flow and connection.
(11)

Mahana 1119

2 Beds
2 Baths
6 Sleeps

Starting at $412/night

    Enjoy your meals or a glass of wine on the lanai, with sweeping views of the ocean and tropical landscape. The bright and spacious living room features comfortable seating and stylish decor, with large doors that open to the lanai The modern kitchen is fully equipped with stainless steel appliances, sleek countertops, and a breakfast bar The dining area offers breathtaking ocean views through large windows and sliding doors, creating a perfect setting for enjoying meals The spacious primary bedroom features a king-sized bed and direct access to a private lanai, offering a peaceful retreat with lush garden views. The modern bathroom offers dual vanities with sleek countertops and stylish round mirrors. The living room features comfortable seating, high ceilings, and large windows that let in natural light
(24)

Kapalua Ridge 1421

1 Beds
2 Baths
4 Sleeps

Starting at $294/night

    Take in the breathtaking ocean views and feel the warm tropical breeze from this stunning beachfront spot from Kaanapali Shores 502 The living room offers panoramic ocean views through floor-to-ceiling windows, creating a serene space for relaxation. The open kitchen leads into a bright living area with stunning ocean views, making it an ideal space for cooking and entertaining. The dining area offers a beautiful view of the ocean, creating the perfect setting for meals while enjoying the island breeze. This serene bedroom boasts direct access to a private lanai with stunning ocean views, perfect for starting or ending your day in relaxation. Enjoy a sun-soaked afternoon or a peaceful moment on the private lanai, complete with comfortable lounge chairs. Take in the stunning panoramic views of the ocean and nearby islands, a perfect backdrop for a day of relaxation by the shore.
(52)

Kaanapali Shores 502

2 Beds
2 Baths
6 Sleeps

Starting at $468/night

    Mahana 508-Come soak in this view Open living and dining space with breathtaking ocean views. Bright and spacious kitchen with seamless flow to the living area and ocean views. Enjoy your meals with a breathtaking ocean view in this bright and inviting dining area. Relax in the serene primary suite, featuring direct access to a private lanai with stunning ocean views. Separate vanity from the shower, perfect for getting ready for your special dinner Relax in comfort while enjoying stunning ocean views from the living room.
(12)

Mahana 608

1 Beds
1 Baths
4 Sleeps

Starting at $292/night

    Enjoy a refreshing drink while taking in the scenic views of lush greenery and the ocean view Relax in this cozy living space with comfortable seating, beautiful natural light, and stunning views of the outdoors Enjoy meals together in this inviting dining area, featuring stylish seating and a contemporary design This modern kitchen is fully equipped with stainless steel appliances, sleek cabinetry, and ample counter space This bright and inviting bedroom features a cozy bed and opens to a private lanai This stylish bathroom features a spacious walk-in shower and a well-lit vanity area Enjoy a peaceful moment on the lanai, perfect for sipping a morning coffee or unwinding with a glass of wine

Holiday Availability

(7)

Kapalua Ridge 2321

1 Beds
2 Baths
4 Sleeps

Starting at $205/night

    Relax on the lanai with stunning ocean views, perfect for enjoying a refreshing drink while soaking in the serene surroundings. A bright dining area with large windows and ocean views, perfect for enjoying meals with a view. Gather in the inviting living room, featuring plush seating and a vibrant ambiance perfect for movie nights or simply unwinding after a day of adventure. The kitchen offers modern appliances and ocean views, making meal preparation a breeze while enjoying the stunning scenery. The elegant dining area is perfect for intimate meals, with vibrant blue accents and beautiful views through floor-to-ceiling windows, creating an inviting space to enjoy your surroundings. This cozy bedroom features a luxurious canopy bed with soft drapery, perfect for enjoying a peaceful night's sleep while soaking in the fresh island air from the nearby lanai. Stunning view of the ocean with clear blue skies, framed by palm trees swaying in the breeze, offering a peaceful and tropical atmosphere
(10)

Wailea Ekolu 1106

2 Beds
2 Baths
6 Sleeps

Starting at $321/night

    The granite countertops and wood cabinetry provide a warm, inviting space for preparing meals This oceanfront balcony provides a perfect setting for enjoying a refreshing drink while soaking in panoramic views of the Pacific. This bright and inviting living area features floor-to-ceiling windows with stunning ocean views. Whether enjoying coffee or a meal, this space allows you to relax while taking in the beautiful scenery beyond Relax and unwind with breathtaking ocean views right from your king-sized bed. Cozy and private ocean front dining Enjoy panoramic ocean views from this cozy and inviting living space.

New Years Availability

(4)

Mahana 1118

1 Beds
1 Baths
4 Sleeps

Starting at $308/night

    Relax on the lanai with a refreshing drink and enjoy the view of the garden and ocean in the distance. The open-concept living and dining area offers a comfortable space to relax and enjoy the view through large sliding doors. The fully equipped kitchen offers modern appliances and a convenient layout, perfect for preparing meals The dining area is perfect for casual meals or enjoying a snack at the breakfast bar The spacious bedroom features a comfortable king-sized bed and a calming, beach-inspired decor. The modern bathroom features a sleek vanity and a glass-enclosed walk-in shower for a relaxing experience. Relax on the lanai with a refreshing drink while overlooking the pool and tropical surroundings.
(21)

Kaanapali Shores 213

2 Beds
2 Baths
6 Sleeps

Starting at $308/night

    The living and dining areas offer plenty of seating, creating a comfortable space to relax, dine, and unwind. Relax in the open living area that leads out to the lanai, offering a comfortable space for dining and lounging. The kitchen island provides ample space for meal prep and doubles as a perfect spot for casual dining or conversation with those in the living room. Relax on the lanai with a view of the ocean, the perfect spot to enjoy a morning coffee or an evening drink. Relax on the lanai with a view of the resort pool, the perfect spot to enjoy a morning coffee or an evening drink. Relax by the pool and enjoy the sunshine in this tropical paradise. Kaanapali Shores 903 Aerial view
(11)

Kaanapali Shores 903

2 Beds
2 Baths
6 Sleeps

Starting at $274/night

    Enjoy a refreshing drink on the balcony with views of the resort and ocean beyond. Relax in the comfortable living room with views of the balcony and resort. The kitchen is equipped with stainless steel appliances and offers plenty of counter space, ideal for meal preparation. The dining area features comfortable seating for four, with natural light flowing in from nearby windows The bedroom features a comfortable bed, large closet space, and a ceiling fan to keep you cool. Enjoy a refreshing drink on the balcony while taking in the view of the pool and ocean. Relax in the open living area that leads out to the lanai, offering a comfortable space for dining and lounging.

Holiday Availability

(11)

Kaanapali Shores 746

1 Beds
1 Baths
4 Sleeps

Starting at $227/night

    The vibrant tropical flowers surrounding the pool create a colorful and inviting atmosphere, with the ocean as the perfect backdrop for relaxation. The cozy living area offers comfortable seating with direct access to the lanai, perfect for relaxing while enjoying views of the garden and ocean. The open-concept living and dining area features large windows that bring in natural light and provide beautiful garden views. The kitchen opens to the bright living and dining area, allowing you to prepare meals while enjoying garden views. The serene bedroom features a comfortable king-sized bed and cozy seating area. The bathroom features a spacious vanity with plenty of counter space and a well-lit mirror, along with a walk-in shower. The cozy living area features a vibrant coastal design with comfortable seating, perfect for unwinding, and direct access to the lanai.

Holiday Availability

(10)

Papakea K-105

2 Beds
2 Baths
8 Sleeps

Starting at $274/night

    Enjoy sweeping ocean views from this spacious, covered lanai, where stylish tile flooring complements the home's first floor. It's the perfect spot to relax in the shade, savoring tropical breezes in ultimate comfort. Relax in the comfortable living room with natural light pouring in through the sliding glass doors This fully remodeled kitchen boasts sleek stainless steel appliances, complemented by granite countertops and modern cabinetry, making it a perfect space for preparing meals with ease and style. The bright, open-concept living and dining area is designed for relaxation and entertainment, with stunning floor-to-ceiling windows that offer panoramic ocean views. This spacious primary suite offers a serene retreat with a king-sized bed, brand new carpet, large windows, and direct lanai access that showcases expansive ocean views. Perfect for unwinding while taking in the stunning surroundings. This elegant bathroom offers a luxurious freestanding tub, perfect for a relaxing soak after a long day. Enjoy breathtaking ocean views from this cozy lanai, perfect for morning coffee or evening cocktails.
(12)

Kapalua Ridge 1622

2 Beds
3 Baths
6 Sleeps

Starting at $480/night

    The spacious lanai offers comfortable seating and beautiful ocean views. This open-concept living area connects seamlessly to the lanai, providing a perfect space to unwind and enjoy the ocean breeze. The kitchen features a cozy breakfast bar with seating for two, ideal for a quick meal or morning coffee. The open dining area provides seating for six with easy access to the lanai. Enjoy a peaceful view from the lanai surrounded by lush greenery and a glimpse of the ocean. Relax and unwind in this cozy outdoor seating area, perfect for enjoying the surrounding garden views. Comfortable seating on the covered lanai offers a great spot to relax and take in the tropical surroundings.

New Years Availability

(35)

Wailea Ekolu 1605

2 Beds
2 Baths
6 Sleeps

Starting at $322/night

  • 1
  • 2
  • 3
  • 1
  • 2
  • 3