Cottage vacation rentals in Kailua

4.98 out of 5 average rating, 51 reviews

Cottage in Waianae

Stargazing Mountainside Cottage by Pristine Beach

Aloha! Come and rejuvenate yourself in this serene retreat in the beautiful Makaha Valley. The cottage offers a refreshingly elegant interior design and lush tropical landscape. The backyard presents stunning mountain views, perfect for morning coffee and stargazing at night. Additionally, it is conveniently located near a 7-mile stretch of pristine beaches, allowing guests to enjoy the beauty of the coast and the tranquility of the mountains in one location. 24/7 customer support by Kalo Homes.

Cottage in Makaha Valley

Support LOCAL: NEW! Mākaha Valley Home

🌺 Mahalo (thank you) for choosing to support LOCAL! 🤙🏻 We know you have many options available to you in this neighborhood from big corporations and companies, but we promise that you will be pleased with your decision. 😊 You may have noticed, there is no AirBnB Service fee AND many discounts. We CHOOSE to incur the 15% service fee with discounts as a way to show our appreciation to you for choosing LOCAL. SUPER family friendly home with minimalist design, cribs, high chairs, and more!

Cottage in Waimanalo

Waimanalo Beach Cottage 9 Studio with Kitchenette

Stay safe with us! Hawaii state Minimum mandated 14 night during COVID 19 from March to October 15, 2020. Outside of this month we have a 5-night minimum stay. This listing includes cottage 8, 9. 10 and 11. All have a separate entrance and kitchens. Historical Waimanalo Beach Cottages since 1957 is a unique quite get away from the noises of Waikiki. Our super cute beach community attracts guests from all over the world looking to experience a piece of Hawaii and the most amazing sunrises!

4.94 out of 5 average rating, 80 reviews

Cottage in Waialua

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

Hawaii’s Best Kept Secret: The cottage is next to sandy coves, driftwood, shells, and forested pastures filled with polo ponies. The ocean is excellent for snorkeling and fishing; there are two surf breaks within one mile, windsurfers get wind most afternoons, and the mountains behind us offer good hiking trails. The Colony has a nice pool and a large grass chipping green, and a tennis court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021.

Cottage in Waimanalo

4.5 out of 5 average rating, 4 reviews

Waimanalo Beach Cottage 5

Stay safe with us! Perfect for large groups and events. Hawaii state Minimum mandated 14 night during COVID 19 from March to October 31, 2020. Outside of these month we have a 5 night minimum stay. Perfect for large groups. 9 Amazing Cottages. Sleeps 24 to 30 guests Historical Waimanalo Beach Cottages is a beautiful country getaway. Steps from beautiful Waimanalo Beach where you see the most amazing sunrise. Our business is a Hawaii State Licensed vacation rental. Mahalo!

4.91 out of 5 average rating, 67 reviews

Cottage in Waiʻanae

MAKAHA SURF BEACH - Oahu, HI

Rustic 2 bedroom cottage located on beachfront property. Fenced yard and gated access to beach. I have lived here over 30 years and still think it the best beach and area. Please read National Geographic Feb 2015 "Hawaiian Renaissance" for more. To clarify: The rate per night is based on 1-2 adults. Thereafter it is $25 per night per adult up to 4 maximum. Also, if you don't see dates or availability for the time you are interested in on my calendar please send me an inquiry.

Cottage in Waimanalo

4.83 out of 5 average rating, 6 reviews

Waimanalo Beach Cottage 4

Perfect for large groups! Historical Waimanalo Beach Cottages is a beautiful country getaway. Steps from beautiful Waimanalo Beach where you see the most amazing sunrise. Our business is a Hawaii State Licensed vacation rental. We offer nine spacious cottages that comfortably accommodate up to 24 guests. We have full-size kitchens that include the comforts of home with your family and friends. Our local grocery stores are nearby making your stay relaxed and affordable.

Cottage in Waimanalo

4.89 out of 5 average rating, 9 reviews

Waimanalo Beach Cottage 1O

If you don’t love the out doors or the tropics including cats, birds, little critters such as ants and geckos including the salt air causing rust In certain areas. Stop here this is not a place for you. Historical Waimanalo Beach Cottages is an awesome country getaway. Steps from Waimanalo Beach where you see the most amazing sunrise. Our business is a Hawaii State Licensed Short term vacation rental. Offering nine cottages that comfortably accommodate 24 guests.

4.97 out of 5 average rating, 92 reviews

Cottage in Haleiwa

Tiny living! Quaint Haleiwa cottage

****Calendar is not always accurate, please inquire for availability. ******* Newly built cottage, equipped with everything to make your vacation a home away from home. High vaulted ceilings make the small home feel spacious, full kitchen for home cooked meals, a large covered deck for outdoor dining. In the heart of historic Haleiwa town, near Starbucks and 7-11, shopping and food trucks are down the street. We are located on site should you have any issues.

Cottage in Waimanalo

Waimanalo Beach Cottages 6

Waimanalo Beach Cottages is Perfect for large groups. We are Steps from beautiful Waimanalo Beach where you see the most awesome sunrise. We are in the tropics and you will experience occasional ants and geckos. We have cats and birds who live on property. We are so close to the beach the salt air does create rust. If this is not OK with you then please don’t book. What we do offer is a beautiful country getaway steps from the ocean and fresh air.

Cottage in Waimanalo

4.33 out of 5 average rating, 6 reviews

Waimanalo Beach Cottage 8 Sleeps 4

All have a separate enterance and kitchens. Historical Waimanlao Beach Cottages since 1957 is a unique quite getaway from the noises of Waikiki. Our super cute beach community attracks guests from all over the world looking to experience a piece of Hawaii and the most amazing sunrises! We are close to Kailua and Hawaii Kai. Two great locations for dining and shopping. Near by Hiking trails are a most to see the beautiful views of East Oahu.

4.79 out of 5 average rating, 90 reviews

Cottage in Haleiwa

2 Bedroom Ocean View Cottage. Walk to great Surf!

A hidden gem, this cozy 2 bd. has all for comforts of home. Fully equipped Kitchen + full size washer and dryer. Full bath with shower + tub. Dinning area and small living area w/flat screen TV inside with a good size outdoor covered deck with a stunning ocean view and an ample size patio table for outdoor dinning. 5 min walk to the beach + short walk to most famous surf spots. Go to: "the tree house hawaii dot com"

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Kailua cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a pool

4.91 out of 5 average rating, 67 reviews

Cottage in Waiʻanae

MAKAHA SURF BEACH - Oahu, HI

Cottage in Makaha Valley

Support LOCAL: NEW! Mākaha Valley Home

4.91 out of 5 average rating, 35 reviews

Cottage in Kailua

Kailua Ohana Cottage close to beach

4.94 out of 5 average rating, 80 reviews

Cottage in Waialua

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

Show all

Pet-friendly cottage rentals

Cottage in Waimanalo

4.38 out of 5 average rating, 8 reviews

Waimanalo Beach Cottage 3

4.79 out of 5 average rating, 90 reviews

Cottage in Haleiwa

2 Bedroom Ocean View Cottage. Walk to great Surf!

Cottage in Makaha Valley

4.5 out of 5 average rating, 4 reviews

Support LOCAL: NEW! Mākaha Valley Home

Cottage in Waimanalo

Waimanalo Beach Cottage 5

Cottage in Waimanalo

4.89 out of 5 average rating, 9 reviews

Waimanalo Beach Cottage 1O

Cottage in Waimanalo

4.83 out of 5 average rating, 6 reviews

Waimanalo Beach Cottage 4

Cottage in Waimanalo

Waimanalo Beach Cottages 6

Cottage in Waimanalo

4.33 out of 5 average rating, 6 reviews

Waimanalo Beach Cottage 8 Sleeps 4

Show all

Private cottage rentals

4.98 out of 5 average rating, 173 reviews

Cottage in Honolulu

Bright and Airy in Paradise: Month-Long Retreat

4.91 out of 5 average rating, 35 reviews

Cottage in Kailua

Kailua Ohana Cottage close to beach

4.97 out of 5 average rating, 92 reviews

Cottage in Haleiwa

Tiny living! Quaint Haleiwa cottage

4.84 out of 5 average rating, 51 reviews

Cottage in Haleiwa

Banzai Pipeline Beachfront home

4.91 out of 5 average rating, 67 reviews

Cottage in Waiʻanae

MAKAHA SURF BEACH - Oahu, HI

4.98 out of 5 average rating, 51 reviews

Cottage in Waianae

Stargazing Mountainside Cottage by Pristine Beach

4.79 out of 5 average rating, 90 reviews

Cottage in Haleiwa

2 Bedroom Ocean View Cottage. Walk to great Surf!

Cottage in Makaha Valley