Kalaheo vacation rentals

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Top-rated vacation rentals in Kalaheo

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Guest favorite

Guest suite in Koloa

4.98 out of 5 average rating, 386 reviews

SUITE DREAMS 3 min. walk to beach Air Conditioning

Located in the UPSCALE POIPU KAI RESORT, on a tropical greenbelt, that borders 2 beaches. This is an attached 1 bedroom 1 full bath suite with a Jacuzzi tub, large walk-in shower & kitchenette. PRIVATE entry & a private fenced outdoor area with a large covered Patio. 3 min walk along a peaceful greenbelt to the BEACHFRONT GRAND HYATT RESORT & SPA. Walk to Beaches, Pool, Hot Tub, Spa, Golf, Tennis, Restaurants, Bars, Nightlife, Luau, and Shops Private off-St. parking. 24 hr. security patrol.

Oct 14 – 21

G$63,610 GYD per night

Guest favorite

Condo in Koloa

4.98 out of 5 average rating, 231 reviews

Slice of Kiahuna Paradise-A/C-BEACHFRONT-POOL

Remodeled bright & breezy top floor, corner unit in exclusive Bld 23. Steps away from top rated Poipu Beach. View. Whole home A/C (dual split in living room & window unit in bedroom). Super fast Wifi. New master bed & queen sleeper sofa in the living room comfortably sleeps up to 4 people. New living & dining furniture and appliances. 65” Smart tv. Unit is supplied w/extra amenities, suggested experiences & babysitting recommendations around the island to offer a fantastic & unforgettable stay!

Oct 27 – Nov 3

G$135,995 GYD per night

Superhost

Condo in Koloa

4.81 out of 5 average rating, 134 reviews

Bamboo Retreat

PK 136 is a quiet, ground floor, private, affordable condo steps from the pool or beach in sunny Poipu. A well appointed unit, it is one of the best bargains in Poipu. Besides the king size bed, full couch, & complete kitchen, the studio has a separate dressing room and bath, closet space, and a small lanai. The unit has free wifi. The common area has a pool, grill area, laundry, & parking spot. Smoking is prohibited in the unit, and permitted only in the designated smoking area on the grounds.

Apr 10 – 17

G$36,121 GYD per night

Guest favorite

Bungalow in Kalaheo

5.0 out of 5 average rating, 101 reviews

Eco Luxe Villa, Infinity Pool

No house should ever be on a hill or on anything. It should be of the hill, belonging to it. Hill and house should live together, each the happier for the other." -- Frank Lloyd Wright Nestled in the Kalaheo hills 20 minutes north from Poipu, this oasis offers modern barefoot luxury with breathtaking views of the lush tropical landscape. The Longhouse has full privacy from the main residence located on the same parcel, it is the place to unplug and unwind, surrounded by nature's beauty.

Dec 16 – 23

G$216,248 GYD per night

Guest favorite

Guesthouse in Koloa

4.99 out of 5 average rating, 147 reviews

Poipu Tropical Retreat with AC & Pool/Gym Access

Discover beautiful Kauai from this spacious 1 bedroom vacation home, built in 2018, in the heart of sunny Poipu. Located in Poipu Beach Estates, the newest upscale neighborhood bordering the Kiahuna Golf Course, that is just minutes from the best beaches on Kauai, shops and restaurants. Create lifetime memories from this modern retreat with its tropical Asian decor. This is a stand alone house, very private, not an apartment. Enjoy a complimentary Poipu Beach Athletic Club membership.

May 28 – Jun 4

G$85,347 GYD per night

Guest favorite

Condo in Princeville

4.99 out of 5 average rating, 210 reviews

Sea and Sky Kauai, an Oceanfront Penthouse

This modern and newly renovated honeymoon beach retreat has breathtaking panoramic ocean and coastline views. Lounge in the daybed while gazing at the sweeping vista from Anini reef to Kilauea Lighthouse. Some have said "it feels like being on a ship at sea" as they witness whales breaching in the ocean and waves peeling on the reef from this magical location. A rare penthouse unit with high ceilings, views from every room, even the famous Bali Hai from the deck. Truly a couple's dream!

Jan 27 – Feb 3

G$116,710 GYD per night

Superhost

Guesthouse in Koloa

4.89 out of 5 average rating, 193 reviews

Luxury Beach Cottage, Sleep 4, walk to beach/shops

This 1 bed/ 1 full bath unit is nestled on the 2nd floor above the garage, with another home located on the property. It has a full kitchen, BBQ, split system AC, memory foam beds, and beach gear included. Poipu Beach is the best place to stay on Kauai. Within a few miles from the house you have, great surf spots, hiking, snorkeling, diving, fishing spots, world-class golfing, excellent restaurants and local boutique shops. Come to the south shore of Kauai for an ultimate get away.

Sep 29 – Oct 6

G$69,029 GYD per night

Guest favorite

Condo in Koloa

4.9 out of 5 average rating, 263 reviews

Garden Isle Condo

Welcome to the garden island condo, just steps away from the wonderful temperate Hawaiian waters and well within walking distance of most of your needs, local restaurants, stores, Starbucks, Poké you name it. Affordable accommodations that allow you to spoil yourself on other things. Plenty of open and covered parking available. Quiet, friendly and inviting, allowing you complete freedom to explore the Island and relax when you return. Settle in and let the adventure begin!!!

Oct 7 – 14

G$43,902 GYD per night

Superhost

Cottage in Hanalei

4.93 out of 5 average rating, 270 reviews

Romantic Garden Cottage,View! Pool! TVNC#1065

Escape to a romantic paradise, tucked away on an acre of lush gardens in the dazzling Wainiha River Valley. Perched atop a bluff overlooking the valley, you are immersed in the serenity and opulence of your private pool and spa, surrounded by vibrant colors and lush greenery, creating a truly surreal and romantic atmosphere. Just miles away, discover some of the world's most beautiful beaches. Let this idyllic retreat transport you to a world of pure romance and bliss.

Nov 26 – Dec 3

G$141,435 GYD per night

Superhost

Home in Hanalei

4.95 out of 5 average rating, 184 reviews

Nico Hale

Our home was recently voted one of the best Airbnbs in Hawaii by Conde Nast Traveler. The home is a secluded jungle cottage on the North Shore of Kauai. We are located just a short drive from local beaches and hikes on the north shore of Kauai in the neighborhood of Wainiha, which is 15 minutes from Hanalei town. The home is surrounded by lush tropical jungle, fruit trees and sweeping jungle views from every window. Listing photos have been updated June 2023 Mahalo

Sep 5 – 12

G$143,810 GYD per night

Guest favorite

Guest suite in Princeville

4.92 out of 5 average rating, 283 reviews

Cozy & private guest suite in Princeville with AC

Clean, quiet and comfortable guest suite in Princeville. Lockout room on opposite side of the main house with private entrance and parking space. The room has a queen bed, mini-fridge, microwave, keurig, WiFi, smart TV and AC. New en-suite bathroom with walk-in shower. Small seating area outside, perfect spot to enjoy a morning cup of coffee. Small cooler provided. Within walking distance to Happy Talk, Hanalei Bay Resort, Queen’s Bath and Hideaways.

Feb 1 – 8

G$29,577 GYD per night

Guest favorite

Condo in Kapaa, Kauai

4.81 out of 5 average rating, 372 reviews

Ocean view Studio in Hotel complex - Kauai

Kamaaina discount offered!! Ocean view condo in a Hotel complex, near the town of Kapaa. 3 adults max in the space. Ocean, pool and garden views. Just steps from the beach and the pool. Beautiful Hawaiian décor. The Islander on the beach, is a quaint Beachfront condo/hotel on 6 pristine acres of tropical paradise. Ground floor studio with two queen beds with private bathroom. Beautiful Air conditioning. Great WIFI/ Cable TV. Double clean between guests.

Feb 11 – 18

G$38,280 GYD per night