Kailua Vacation Homes

<p><b>Kailua Vacation Homes </b><br>Kailua, the bustling beach town of Oahu - the heart of Hawaii - is only 30 minutes away from Honolulu and Waikiki and a favorite destination for visitors to soak up some Hawaiian fun and sun. If you're one of the many lured by Kailua's green cliffs, turquoise waters, botanical gardens, and soft white sands, we've got the perfect Kailua vacation home for you so you can explore this Windward Coast town that's the perfect blend of beautiful city and country island attractions. <br></p><p><b>Experience Kailua </b><br>With our selection of first-class Kailua vacation homes, you'll find properties that boast both sophisticated elegance and untapped island elements. Choose from modern beachfront accommodations that are steps to the beach or pick a plantation cottage that provides you that perfect Hawaiian retreat. Luckily, all of our Kailua homes are in close proximity to the world's best beaches so you can shop, snorkel, windsurf, or just read a good book. When you've had enough sun and sand, opt for a jaunt into Kailua Town for some shaved ice or a souvenir from one of Kailua's unique boutiques. Finally, don't forget to get some picture perfect photos on the one-hour Lanikai Pillbox hike, a great trail with stunning vistas that overlook Kailua and Lanikai. <br></p><p><b>Oceanfront Kailua Homes </b><br>The perfect ambiance for adventure and fun, Kailua Beach is one of the world's ultimate windsurfing and sailing destinations. Ocean lovers will appreciate the warm Pacific that invites them to try a variety of water activities including kiteboarding, kayaking, and scuba diving. With a gorgeous Kailua vacation property to call home, all of the town's main attractions are within reach. <br></p><p>If you prefer to eat, savor the delectable cuisines from a number of top-rated Kailua restaurants. Many feature farm-to-table dishes so you can taste the fresh offerings unlike anywhere else in the world. If shopping is on your agenda, head to the…

20 vacation rentals found. Page 2 of 2 shows 10 properties (10 per page, same as the live site).

Kailua Vacation Homes

Page 2 of 220 properties total — 10 per page (matches site listing view).

Lanikai Ohana Hale - 1BR Home Garden View + Private Pool

Kailua, Oahu
  • 1 Bed
  • 1 Full Baths

From $225.00 / night — Total price: $675.00

Discover your private island retreat at Charming Cottage in Lanikai by Gather, a beautifully renovated 1-bedroom, 1-bath home surrounded by lush tropical gardens. Fully remodeled in 2021, this peaceful hideaway blends modern comfort with the timeless charm of Lanikais coastal lifestylejust a short stroll from one of Oahus most beautiful beaches. What Youll Love About This Lanikai Cottage Newly renovated in 2021 with brand-new furnishings and appliances Peaceful tropical setting with privacy a

Lanikai Ohana Hale - 1BR Home Garden View + Private Pool

Makana's Place

Kailua, Oahu

Rating: 4.9

  • 1 Bed
  • 1 Full Baths

From $600.00 / night

Makana's Place is a one bedroom, one bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1400 square feet living quarters, which is equivalent to a three bedroom home. Beautifully decorated with fine quality furniture (Koa). Makana's Place features a full kitchen plus an extra queen sofabed and single bed. Wonderful for children. The beach, yes the beach. It is about a 5 minute drive away or 15 minute walk. It has been rated the #1 beach in "best beaches" survey. Most pe

Makana's Place

Makana's Place 3 Bedroom 2 bath home

Kailua, Oahu

Rating: 4.7

  • 3 Bed
  • 2 Full Baths

From $1200.00 / night

Makana's Place is a 3 bedroom, one bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1600 square feet living quarters, which is equivalent to a 4-5 bedroom home. Beautifully decorated with fine quality furniture (Koa). Makana's Place features a full kitchen plus kitchenette with 2 rooms, 1 bath an extra queen sofabed and single bed located in the extra large spacious living room. There is a very cozy patio area with a fountain and beautiful cooper lighting to enjoy out

Makana's Place 3 Bedroom 2 bath home

Manuela Place

Kailua, Oahu

Rating: 5

  • 3 Bed
  • 3 Full Baths

From $1485.00 / night

Manuela is a quiet spacious home, in charming Kailua town. This non-smoking home has 1400 square ft of living quarters. It is a 3 bedroom 3 bath home with a front patio and small yard safe for your children. Living and Dining room equipped with a spit A/C for your comfort. All bedrooms have air conditioning as well!!! Kailua beach is about a 3 minute drive or 10-15 minute walk. We take pride in our home and will make sure you enjoy your stay with us. There are many places to go see, ea

Manuela Place

Monet Room - Studio Cottage

Kailua, Oahu

Rating: 5

  • Studio
  • 1 Full Baths

From $235.00 / night — Total price: $705.00

Enjoy our Hawaiian sunshine and one of the most beautiful beaches in the world. Our studio has high ceiling with a Monet- designed decor. A Large queen size 4 poster bed, with a sitting area and dining area. There is a breakfast bar which includes a hotel sized refrigerator micro-wave oven, coffee maker, toaster, small rice cooker and a gas BBQ grill outside. This is truly island living at its finest. Residence has its own private entrance, private patio with umbrella table, parking and a large

Monet Room - Studio Cottage

Nani's Cottage - 2BR Home

Kailua, Oahu

Rating: 4.8

  • 2 Bed
  • 2 Full Baths

From $450.00 / night — Total price: $1350.00

This unit is brand new to the Vacation Rental market. A quaint 2 bedroom, 2 bath cottage is perfect for a small family. Enclosed property with front yard space for playing on the grass. A beach access is just 1 house over, so in about 1 minute walk you will be on the sand at a portion of beautiful Kailua Beach. Downstairs has a split system AC which cools the living area, kitchen and master bedroom. Extra person Fee of $25 per night per person after the 4th guest. This property is a le

Nani's Cottage - 2BR Home

Ocean Escape - 5BR Home

Kailua, Oahu

Rating: 5

  • 5 Bed
  • 4 Full Baths

From $3150.00 / night

This is a legally established property, please read below for more info... Hawaiiana home just steps from the world famous Kailua Beach. This Hawaiiana house second of two homes of the beachfront property. It is the perfect place to relax and enjoy paradise. The tropical large living room opens onto a spacious private lawn leading out directly via a secure gate beteen the two homes to a sandy walkway, steps to breathtaking Kailua beach. A rear private courtyard lanai with 15ft x 32ft

Ocean Escape - 5BR Home

Serenity Beachfront Cottage - 2BR License Number 90-TVU-0326

Kailua, Oahu

Rating: 4.9

  • 2 Bed
  • 1 Full Baths

From $1500.00 / night

Licensed-Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three miles of pristine white sand and turquoise water. Wander down to the local market for lunch, and picnic under the palm trees. Rinse off in your tropical outdoor shower before settling in for sunset. The cottage includes a c

Serenity Beachfront Cottage - 2BR License Number 90-TVU-0326

Tranquility Beachfront - 3BR Home

Kailua, Oahu

Rating: 4.9

  • 3 Bed
  • 3 Full Baths

From $2775.00 / night

Enjoy sunrises from the deck overlooking the beach, and sunsets from your own private perch in the sand. This beautifully decorated 3 bedroom beachfront home pampers you with a large, well-appointed kitchen, upstairs master suite with soaking tub and killer views. A large living room and dining room invite your Ohana to gather. The private den is ideal for curling up with a book, and so much more. From the kitchen, hear the birds sing, and the crashing of waves only steps from your retreat in pa

Tranquility Beachfront - 3BR Home

Tropical Breeze - Studio Cottage

Kailua, Oahu

Rating: 4.8

  • Studio
  • 1 Full Baths

From $325.00 / night — Total price: $975.00

Serene tropical comfort in your own private studio, just steps away from 1 of the top 5 best beaches in the world. Here you can walk for miles on a white, sandy beach or go wind surfing, kite sailing, boogie boarding, kayaking, snorkeling, or swimming. Kailua beach is truly special. The Tropical Breeze studio boasts garden views, tropical trade winds and the soothing sounds of the ocean waves. Come and enjoy the aloha spirit and warm sunshine. The studio has high ceilings with a tropical-d

Tropical Breeze - Studio Cottage