Chesapeake Vacation Rentals
<div class="aboutUsText"><p>Our Hawaii vacation rentals provide affordable and luxurious places to stay in all of the most desirable areas of Hawaii, from the excitement of Honolulu and Waikiki on Oahu to pristine, remote locations on the outer islands of Maui, Kauai, Molokai, and the Big Island for a Hawaii vacation experience you will remember the rest of your life.</p></div>
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<h3>Things To Do</h3>
<p><span class="aboutTextLeft"></span> On Oahu enjoy a spacious north shore vacation rental home or luxury appointed Turtle Bay condo, both near the world-famous surfing beaches of Banzai Pipeline, Waimea and Sunset Beach. Heading over to the windward side take advantage of award winning, postcard-perfect beaches in one of the Lanikai Beach rentals or Kailua vacation rentals set on immaculate white sands and crystal blue water, where kayaking and windsurfing are popular along with bodysurfing and snorkeling.<br><br>On Oahu's southern shore enjoy a convenient location near historic downtown Honolulu or seaside in a condo on the famous beaches of Waikiki. Nearby you can stay at the elegant Ko'Olina Resort area or in a luxury vacation rental in the prestigious neighborhoods of Diamond Head and Black Point where the only sounds will be waves lapping at the shore.<br><br>On Maui we offer accommodations in all the finest areas from the scenic Makena and Wailea condos to the white-sand beaches of Kaanapali and Kapalua. You can also stay in vibrant Lahaina town or Kihei, in lush and tropical Hana with its many waterfalls and scenic beaches, or near the flower farms of Upcountry Maui on the slopes of Haleakala.<br><br> On Kauai's sunny south side, enjoy the luxury of a Poipu condo in a resort area lined with beautiful beaches with great snorkeling and swimming areas. Poipu luxury rentals also provide the opportunity for lots of activity including sailing tours, horseback riding, ATV tours, ziplining and hiking trails along the remote Mahaulepu coastline.<br><br>On Kauai's majestic north shore is crescent-shaped Hanalei Bay, an ocean playground cradled by mountains and streaming with waterfalls, and the elegant Princeville Resort with championship golf and other amenities including nearby horseback riding, ziplining, and hikes to swimming holes and waterfalls.<br><br>On the Big Island find a vacation rental or condo in historic Kona known for its sunny weather, great beaches…
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<h3>Eat And Shop</h3>
<p><span class="aboutTextRight"></span>Fresh seafood, exotic fruit or tasty fare are part of just about every menu on Hawaii, whether it's from roadside trucks, local bakeries, sunshine (farmers') markets or upscale seaside eateries. Coconut, macadamia nuts, poi, Kona coffee, breadfruit, poke (tuna that is grilled or sauted) and yes, Spam, are a few of the local foods to explore. The regional Hawaiian cuisine is prepared by some of the world's most innovative chefs.<br><br>Explore open-air markets, boutiques, grand shopping centers overlooking the ocean and seaside art galleries. Visit coffee farmstour, taste and shopwhere you'll enjoy a combination of shopping while sightseeing. Authentic handcrafted items are the top souvenirs, especially those created in front of you, and simply because they are literally a piece of Hawaii to take home. Jewelry, handbags, gourmet food, apparel and candy will fill your bags as easily as shopping for them will fill your days.</p></div>
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<h2>Getting Around</h2>
<p>Hawaii has some public transportation, but the best way to get around is by rental car. Your own schedule, flexibility and the spontaneity of a rental car are benefits to other transport. Nevertheless, on occasion, you may want to see the island and explore without worrying about parking or driving. Take a trolley, shuttle, TheBus or other local transport. Take the ferry between Maui and Molokai for the day. Inter-island travel is easy and the airports are easily navigable, with plenty of taxis and ground transport. Indulge in a limousine for special occasions. Local car rentals are generally more affordable, often with a hotel package and will allow you to select features (convertible, 4WD) that work best for you and the number of people in your travel party</p></div>
893 vacation rentals found. Page 5 of 90 shows 10 properties (10 per page, same as the live site).
Chesapeake Vacation Rentals
Page 5 of 90 — 893 properties total — 10 per page (matches site listing view).
Hale Kaila Hou - 4BR Fairway View Home
Princeville, Kauai- 4 Bed
- 3 Full Baths
From $720.00 / night — Total price: $2160.00
Wake up to rainbows and waterfalls cascading down the lush mountains of Namolokama. Located directly on the golf course in the heart of Princeville, this expansive, high-ceiling estate blends amenities with tropical relaxation at this lovely 4 bedroom home. Unwind in your private wellness backyard, cook in a kitchen with full size appliances, or watch the sunset from the massive slate-tiled lanai. Location Highlights: You are minutes away from Kauais most iconic North Shore destinations Beac
Hale Kamaole - 1BR Condo #215
Kihei, Maui- 1 Bed
- 1 Full Baths
From $139.00 / night — Total price: $417.00
Wake up to a peaceful Maui morning just steps from Kamaole Beach III. Hale Kamaole 215 offers a clean, relaxing retreat in South Kihei, perfect for recharging and enjoying the island at your own pace. Set within a beautifully maintained low-rise property known for its laid-back, residential feel, this condo is ideal for guests looking for a more easygoing Maui experience. Surrounded by lush tropical landscaping, Hale Kamaole offers a comfortable setting while still being close to everything. G
Hale Koaniani - 3BR Ocean View Home
Wainiha, KauaiRating: 5
- 3 Bed
- 2 Full Baths
From $790.00 / night — Total price: $2370.00
TVNCU#1059 - TA# 121-109-0944-01 - "House with the Cooling Breeze" A true oasis, Hale Koaniani is a meticulously cared for three bedroom, two and a half bath home and a rare find on Kauai's spectacular North Shore. Its elegantly constructed and furnished and has ocean and mountain views. Experience exceptional quality with honed black granite counter tops, custom cabinetry, a Sub Zero refrigerator, a Wolf 6 burner range, oven, and a built-in office nook. Waterworks fixtures, and Cumaru hardwood
Hale Kuikahi - 4BR Home Ocean View
Hilo, Big Island- 4 Bed
- 3 Full Baths
From $899.00 / night — Total price: $2697.00
Step onto the grounds of our oceanfront botanical garden retreat - Hale Kuikahi! Located in the quiet Paukaa area of Hilo just above famed Honolii surf beach, Hale Kuikahi boasts a private botanical garden walk onsite. Enjoy sweeping oceanfront views from almost every room in the house. The open kitchen, dining area and living room in the center of the house are accented by large windows and view doors to the ocean. The lanai boasts an overhanging section where you feel like you're on the
Hale Lani - 4BR Home Golf View
Princeville, Kauai- 4 Bed
- 3 Full Baths
From $532.60 / night — Total price: $1597.80
Experience the best of Kauais North Shore at Hale Lani, a beautifully designed 4-bedroom, 3-bath home in the exclusive Princeville community. With air conditioning throughout, breathtaking views of the Makai Golf Course and Bali Hai mountains, and a quiet cul-de-sac location, this is your ideal island retreat. Just a short walk to the Princeville Centers shops, dining, and park, and a quick drive to Hanalei Bay or Anini Beach for world-class snorkeling, surfing, and sunbathing, Hale Lani is per
Hale Mahina - 2BR Condo Beach Front #B-405
Lahaina, Maui- 2 Bed
- 2 Full Baths
From $199.00 / night — Total price: $597.00
Welcome to Hale Mahina #B-405, a stunning top-floor oceanfront condo in the highly sought-after Hale Mahina Beach Resort on West Maui. Overlooking the Pailolo Channel with panoramic views of Molokai and Lanai, this remodeled two-bedroom, two-bathroom retreat is perfect for seasonal whale watching, breathtaking sunsets, and the soothing sounds of the ocean. Nestled within lush tropical gardens and just steps from a secluded sandy beach, this condo offers the ideal balance of comfort, privacy, and
Hale Mar - 3BR Home Ocean View King
Keaau, Big Island- 3 Bed
- 2 Full Baths
From $599.00 / night — Total price: $1797.00
Hale Mar - Welcome to our Oceanfront vacation home - E komo mai! Panoramic ocean views and the sound of crashing surf from every room, and your own private 38' pool & hot tub! Spaciousness, luxury and privacy located on the Big Island near Hilo and the famous Volcano Park. New home on private 1/2 acre of absolute oceanfront with gourmet kitchen, color TVs with wireless high speed Internet for streaming, fenced and gated, charcoal barbecue, down pillows and high thread count linens, what else ca
Hale Mauka
Volcano, Big IslandRating: 5
- 2 Bed
- 1 Full Baths
From $225.00 / night — Total price: $675.00
Volcano Hale Mauka welcomes you to a lovely private cottage nestled in the middle of the rainforest! Our house is very clean and well appointed. Hale Mauka offers you a place to come home and relax after a long day out exploring and playing. Rates are for up to 4 guests. Do not exceed occupancy of 4. SOAK in our 110 gallon tub for TWO with private rain forest views! Our tub is so insulated that it stays warm for hours! Who needs Jacuzzi or Spa? .. Our two bedrooms are each appointed with co
Hale Moi - Studio Condo Studio King #216
Princeville, KauaiRating: 5
- Studio
- 1 Full Baths
From $250.00 / night — Total price: $750.00
Hale Moi #216A. Welcome to your Garden Island oasis: a stylish island-style retreat in the heart of Princeville. This beautiful, newly renovated studio is your perfect home base for trips to Hanalei town (10 mins) and the incredible beaches on Kauai's North Shore. Enjoy your morning coffee on the spacious, private balcony with mountain views, sprawl out in the laid-back living room after a long day in the sun, and at night, make your way up the spiral staircase to the cozy bedroom for a night o
Hale Napali - 3BR Mountain View Home + Private Hot Tub
Princeville, KauaiRating: 5
- 3 Bed
- 2 Full Baths
From $437.40 / night — Total price: $1312.20
Refreshed in 2024, this beautifully updated home is the ultimate North Shore retreat, located in the prestigious Sunset Drive neighborhoodone of Princevilles most sought-after communities. Guests enjoy exclusive access to a private clubhouse with a pool, tennis court, and designated parking. Just minutes away, youll find Princeville Park, shopping and dining at the Princeville Center, scenic Kenomene Outlook, Hanalei Town, Anini Beach, tropical hiking trails, and local farmers markets. Perfect
