Vacation rentals in Wailua Homesteads

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Top-rated vacation rentals in Wailua Homesteads

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

Cottage in Kapaa

Beachfront Cottage: Romantic and Family Friendly!

Private beachfront cottage with direct access to Baby’s Beach and the coastal bike path, nestled in a charming single-family residential neighborhood. Short walk to Kapa'a shops, restaurants, markets, galleries, and the beach. 2 King bed/1 bath (with tub), soaring vaulted ceilings, living room, fully equipped kitchen, dining areas (inside and out). Convenient to both north and south shores. Private deck with grill, outdoor shower and astonishing views. TVNC 4288/TMK 45002013 TAT066678067201

ValueLocationGrill

4.93 out of 5 average rating, 172 reviews

Guest favorite

The vibrant red exterior of the traditional Hawaiian-style house is framed by lush greenery and palm trees. Large windows allow natural light to fill the interior, while the mountainous backdrop enhances the tropical ambiance. A well-maintained lawn surrounds the property.

Cottage in Hanalei

Kaiolohia Hale Haena Walk to Tunnels Beach

TVNC#1146 - Gated entrance leads you through a 6 foot lava rock wall. The rear, ground level, traditional Hawaiian style house is privately tucked away behind the housekeepers front house. Backyard Lanai commands your attention onto conservation Lands with massive mountain and waterfall views . Cedar wood lined interior walls and local artwork adorn the 1600 square foot house. Walk 1/3 mile to Tunnels Beach 5 minutes Kauai lifestyle Note: property located in tsunami evacuation zone.

ValueFamilyKitchen

4.93 out of 5 average rating, 135 reviews

Superhost

A spacious bed is centered against a neutral wall, topped with white linens and a decorative pillow. On either side, minimalist bedside tables hold modern lamps casting soft light. A vibrant landscape artwork hangs above, depicting lush mountains and a coastal view.

Condo in Kapaa

East Coast Escape

Aloha! Cozy small private studio with all of the necessities! Nestled into the Kauai Kailani complex right on the beach in the centrally located and happening town of Kapa'a. The view from the pool is spectacular. Enjoy the pool directly on the ocean. Biking and walking distance to many local shops, restaurants and the beach! Lots of hiking, Coconut Coast bike path, beaches all within walking distance. Studio has a small kitchenette where you can cook meals, a king size bed, beach gear and more.

FamilyValueOutdoor spaces

4.83 out of 5 average rating, 283 reviews

Top guest favorite

An open-concept living area features a spacious blue sectional sofa and a dining table with wicker chairs. Large sliding glass doors frame ocean views, while vaulted wooden ceilings enhance the airy ambiance. A TV is mounted on the wall, complementing the contemporary decor.

Home in Wailua

Panoramic luxury beachside condo in paradise A/C

Oceanside Paradise. 180 degree Ocean views. Large private Lanai with breathtaking 180 degree views inside and out. See dolphins, whales, turtles, rainbows & amazing sunrises. Steps from beach & centrally located on the famous Coconut Coast & steps from the Lae Nani beach. Beach chairs & gear included. Beautifully remodeled with an open, custom kitchen/baths & vaulted ceiling. Boasts double master suites, Beautiful Pool, BBQ area, beach access, A/C, washer/dryer & private covered parking.

ValueLocationCleanliness

5.0 out of 5 average rating, 187 reviews

Guest favorite

A living area is visible through an open doorway, featuring two light blue chairs facing a wooden table. Large windows allow natural light to illuminate the space, with lush greenery and blooming flowers seen outside, contributing to a refreshing atmosphere.

Home in Wailua

The Lime House 4BDRM 2Bath Steps from the Beach!

The Lime House is centrally located on the island and just steps from one of our favorite beaches! One that Naomi grew up going to almost every day. It’s a beach that is great for the whole family. It is also located just across the street from the Coconut Marketplace where you can find shopping, free hula shows and farmers market! Just down the street is the Wailua river which is great for kayaking or taking a boat ride up to the famous fern grotto. Contact me after your booking for more info!

LocationValueHiking

4.96 out of 5 average rating, 296 reviews

Top guest favorite

A serene coastal view features vibrant blue waters meeting a sandy beach, framed by lush greenery. Two cups are placed on a wooden ledge, inviting a peaceful moment while taking in the expansive landscape under a partly cloudy sky.

Vacation home in Wailua

Beautiful OCEANFRONT Kauai Condo with beach access

Aloha, and welcome, to our Wailua Bay View condo, located on the East shore of Kauai in the Coconut Coast town of Kapa'a. Spectacular panoramic ocean views of the expansive sandy beach of Wailua Bay awaits you. Our 740 sqft. fully equipped ground floor condo features a spacious one bedroom and one bath, a fully equipped kitchen, a washer and dryer, an outdoor swimming pool/ BBQ area.A comfortable living area with a queen sofa/sleeper. We are centrally located to dining and shopping. Wi-Fi, tv.

ValueLocationBreakfast

4.93 out of 5 average rating, 162 reviews

Top guest favorite

A serene bedroom features a spacious bed with light-colored bedding. Large windows surround the room, offering views of the ocean and greenery. Natural light filters through bamboo blinds. A ceiling fan and air conditioning unit provide comfort, with wooden accents adding warmth to the space.

Vacation home in Lihue

Amazing Views from this Oceanfront Home

Enjoy amazing views & soothing ocean sounds from this cliff side home by popular Kalapaki Beach. 2 bedrooms, both with AC plus great ocean & mountain views. Master with en suite has a king bed. 2nd bd has a queen. 2nd bath, washer & dryer in hallway off living room, which has amazing views as well. Fully stocked kitchen. Balcony lanai with table & chairs for outdoor dining. Free parking in this gated community. Nearby elevator takes you to the beach with restaurants and shops nearby.

FamilyValueAir conditioning

4.89 out of 5 average rating, 213 reviews

Guest favorite

A Hawaiian-style home is set against a backdrop of palm trees and vibrant greenery. The exterior features a covered porch and large windows, with an expansive ocean view visible beyond the lush landscape.

Villa in Anahola

Oceanfront BeachHouse-Spectacular Views & Privacy

This beautiful beachfront Hawaiian style home commands a spectacular 220 degree view of the ocean from its large lanai where you can enjoy outdoor dining cool and ocean breezes. This is Hawaii at its best. We're on a small peninsula with our own secluded beach access to snorkeling, surfing, fishing, & paddle boarding. Explore the reef or paddle up the river toward Kong Mountain. This is the Hawaiian island experience that we all dream of. Come enjoy your own secluded piece of paradise.

FamilyLocationOutdoor spaces

4.93 out of 5 average rating, 121 reviews

Top guest favorite

A single-story house is framed by tall palm trees, set on a lush green lawn. The sky is partly cloudy, with bright sunlight peeking through, illuminating the surrounding greenery and creating a serene outdoor atmosphere.

Home in Kilauea

Northshore 5 acres plantation style home TVNC 4273

Northshore Plantation style house 5 acres. TVR-4273 Roomy, Private estate 2 min. drive to old Kilauea town for stores & restaurants. Great for family gatherings or 2 couples. Special spot, short walk down to Kalihiwai Bay & Secret Beach, 2 world class beaches. RELIABLE HIGH SPEED WIFI, perfect for remote-work. Creative property - seasonal fruit trees- avocados, coconuts, lemons, oranges, limes, guava, passion fruit. A truly blessed spot. A successful legal vacation rental since 2006.

ValueLocationTV

4.94 out of 5 average rating, 101 reviews

Top guest favorite

An aerial view showcases a charming cottage surrounded by lush tropical foliage. A private hot tub is nestled on a deck, complemented by a cozy lounging area. Vibrant flowers and greenery create a serene outdoor space, enhancing the sense of seclusion and tranquility.

Cottage in Hanalei

Romantic Garden Cottage,View! Pool! TVNC#1065

Escape to a secluded romantic haven nestled on an acre of lush gardens in Kauai’s breathtaking Wainiha River Valley. Perched on a bluff with panoramic valley views, this retreat offers tranquility and luxury. Unwind by your private pool and spa, surrounded by vibrant tropical flora, where nature creates an atmosphere of enchantment. Just a short drive away, explore some of the world’s most stunning beaches. Let this serene paradise immerse you in romance and blissful relaxation

LocationFamilyBeach

4.95 out of 5 average rating, 404 reviews

Guest favorite

An outdoor dining space is presented with a white table surrounded by six chairs. Lush greenery lines the edge, with views of the ocean and a vibrant sunset in the background. Palm trees frame the scene, creating a serene atmosphere.

Home in Kekaha

Oceanview, Air Conditioning, Clean and Cute

Two bedroom home has dramatic views of the ocean and a cute and comfortable place to call home. We are located just across the street from Davidsons surf break. Located in Kekaha which is loved for its sunny days and laid back vibe. As with most of the ocean view homes in Kekaha we are on Kuhio Hwy directly across from the ocean. Please consider the traffic noise and keep in mind that for most the views far outweigh the road noise.

ValueFamilyDecor

4.9 out of 5 average rating, 376 reviews

Guest favorite

A tranquil cottage is set within a lush landscape, surrounded by various tropical plants and trees. A winding stone path leads to the entrance, enhancing the natural beauty of the yard. Large windows allow for ample natural light to brighten the retreat.

Cottage in Anahola

Sweet Country Cottage

You are invited to a working farm, hosted by a generational Native Hawaiian family rooted in traditional values of mālama ʻāina and communal responsibility. Throughout the property, you’ll find food-bearing trees, native and medicinal plantings, and evolving horticulture projects supporting sustainability and land restoration. Guests may be welcomed to harvest seasonal fruits and or join goat yoga to hear the history of Hawaiʻi.

LocationValueOutdoor spaces

4.83 out of 5 average rating, 111 reviews