Hawaii Two-Bedroom Vacation Rentals
Two-bedroom vacation rentals in Hawaii are the ideal choice for families, couples traveling together, or small groups looking for comfort and flexibility. These spacious accommodations offer separate sleeping areas, fully equipped kitchens, and scenic lanais-perfect for relaxing after a day of island adventure.
Whether you're seeking an oceanview condo in Waikiki, a resort villa on Maui, or a secluded beach cottage on Kauai, our curated list of two-bedroom Hawaii vacation rentals offers something for every traveler. Enjoy the freedom of preparing meals in your own kitchen, gathering with loved ones on the lanai, and retreating to private sleeping quarters for a restful night.
These rentals are located across Hawaii's most popular areas-from the Big Island's Kona Coast and Kailua-Kona to Waikiki on Oahu and Kaanapali on Maui. Many include access to resort amenities like pools, tennis courts, and BBQ areas, and are steps from beaches, golf, and hiking trails.
Key Features of Two-Bedroom Vacation Rentals
- Two separate bedrooms with queen/king beds or bunk/trundle options
- Ideal for families, friends, and multi-generational groups
- Full kitchens and in-unit laundry for added convenience
- Private lanais or patios with ocean, mountain, or garden views
- Locations near beaches, attractions, and dining
- Many rentals with access to resort pools, hot tubs, BBQs
Planning a larger stay? Browse three-bedroom rentals or private estates in Hawaii for even more space and privacy.
Wailea Point | 3203 - 2 Bedroom Ocean View Condo - 30+ Night Luxury Stays
Wailea Point #3203 offers a luxurious and serene retreat with stunning ocean views, located in the exclusive gated community of Wailea Point. This elegant condo is perfect for those seeking privacy and a minimum stay of 30 nights, providing an ideal setting for a...
Wailea Grand Champions 71 - 2 Bedroom Golf Course & Partial Ocean View
Wailea Grand Champions 71 is a beautifully updated ground-floor vacation rental that offers both fairway and ocean views from the living room and private lanai. This spacious two-bedroom, two-bath condo comfortably accommodates up to six guests, providing ample room for...
Wailea Grand Champions 43 - 2 Bedroom Garden View Condo
Wailea Grand Champions 43 is a stunning vacation rental nestled in the heart of Wailea, offering a luxurious escape with breathtaking views and unparalleled comfort. This elegantly designed property is ideal for those seeking both relaxation and adventure on the...
Wailea Grand Champions 31 - 2 Bedroom Golf Course View Condo
Wailea Grand Champions 31 is a recently updated vacation rental that offers a perfect blend of comfort, style, and convenience in the heart of Wailea. This two-bedroom, two-bathroom condo features modern upgrades including granite countertops, new cabinetry, and...
Wailea Grand Champions 183 - 2 Bedroom Garden View Condo
Welcome to Wailea Grand Champions 183, a luxurious vacation rental that perfectly blends comfort and style in the heart of Maui\'s paradise. This stunning two-bedroom, two-bathroom retreat offers an exceptional experience for discerning travelers seeking a memorable...
Wailea Grand Champions 111 - 2 Bedroom Garden View Condo
Wailea Grand Champions Villa 111 is a spacious two-bedroom, two-bath vacation rental condo that accommodates up to six guests, making it an ideal choice for families or friends traveling together. The first bedroom features a comfortable king-sized bed, while the second...
Wailea Beach Villas PH502 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spectacular sunset views all year long. This top floor penthouse has been exquisitely redecorated with an elegant, casual décor. Your private elevator...
Wailea Beach Villas PH411 - 2 Bedroom Ocean View Penthouse
Let the sounds of palm fronds brushing against each other in the gentle trade winds sing you to sleep this vacation. With relaxing views of the ocean and the manicured tropical landscaping, Wailea Beach Villas Penthouse 411 leaves no stone unturned in the pursuit of...
Wailea Beach Villas PH410 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas PH410 is a fourth floor penthouse suite that overlooks the central swimming pool with spectacular views of the Pacific Ocean and Wailea Beach, along with views of Kaho’olawe, Molokini and Lana\'i. From your private elevator landing, the suite opens...
Wailea Elua Village 708 - 2 Bedroom Ocean View Condo
Wailea Elua Village 708 is a luxurious two-bedroom, two-bathroom vacation rental located in the prestigious Wailea community on Maui\'s southern coast. This beautifully remodeled condo offers a serene retreat, accommodating up to six guests, making it ideal for families...
Wailea Beach Villas PH406 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 406 is desirable for its remarkable Pacific Ocean and Island views. This upscale penthouse vacation rental features two bedrooms, two bathrooms, exotic hardwood furnishings, an incredible antiquities collection, and an amazing ocean view....
Wailea Elua Village 705 - 2 Bedroom Garden View Condo
Wailea Elua 705 is an exquisite vacation rental located on the stunning shores of Maui. This newly renovated, two-bedroom, two-bathroom beach house inspired condominium offers a spacious layout ideal for families or groups of friends seeking a luxurious getaway. With...
Wailea Beach Villas PH402 - 2 Bedroom Ocean View Penthouse
Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale watching from your spacious, private lanai with scenic views of the Maui horizon, Molokini Crater and the island of...
Wailea Beach Villas PH307 - 2 Bedroom Ocean View Penthouse
In Wailea Beach Villas PH307 you can immerse yourself in luxe tropical comforts blended with blue ocean views. This delightful Maui ocean view vacation residence will cultivate long lasting memories and leave you feeling rejuvenated upon departure. Centrally located on...
Wailea Beach Villas PH306 - 2 Bedroom Ocean View Penthouse
Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with exceptional ocean and island views are sure to inspire the luxury, comfort and serenity you deserve. Thoughtfully designed...
Wailea Elua Village 2104 - 2 Bedroom Garden View Condo
Wailea Elua 2104 is a charming two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. Designed with an island-inspired aesthetic, this condo blends comfort with contemporary style, making it an ideal getaway for families or groups of friends....
Wailea Beach Villas PH210 - 2 Bedroom Garden View Penthouse
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish...
Wailea Elua Village 2006 - 2 Bedroom Ocean View Condo
Wailea Elua Village 2006 is a charming vacation rental that epitomizes the luxury and tranquility of Maui. This beautifully appointed two-bedroom, two-bath condo offers an ideal retreat for families or friends seeking a relaxing island escape. The residence boasts a...
Wailea Elua Village 1704 - 2 Bedroom Oceanfront Condo
Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches on Maui. This spacious two-bedroom, two-bathroom corner unit spans approximately 1,600 square feet and comfortably accommodates up to six guests,...
Wailea Elua Village 1703 - 2 Bedroom Oceanfront Condo
Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach and the Wailea Beachfront Walking Path. What sets it apart is its unique privacy, surrounded on three sides by lush, meticulously landscaped gardens...
Wailea Beach Villas PH111 - 2 Bedroom Garden View Penthouse
Curated with our guests in mind, Wailea Beach Villas PH111\'s outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine Wailea Beach is located...
Wailea Elua Village 1604 - 2 Bedroom Oceanfront Condo
Expansive unobstructed views of blue Pacific waters and gentle waves will greet you each time you step out onto the lanai and soak in all the beauty that Wailea Elua 1604 offers. Evenings offer gorgeous sunsets framed by swaying coconut palms, perfect for a relaxing...
Wailea Elua Village 107 - 2 Bedroom Ocean View Condo
Located just steps from the beach in the heart of Wailea, Elua Village 107 is a beautifully appointed two-bedroom, two-bathroom ground-floor residence that offers the perfect blend of comfort and island elegance. With a spacious layout and tasteful décor, this vacation...
Wailea Ekolu Village 1107 - 2 Bedroom Ocean View Condo
Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning views of the ocean, mountains, and the island of Lana\'i. Guests can enjoy the soothing sounds of tropical birds without the disturbance of street...
Wailea Ekolu Village 1007 - 2 Bedroom Ocean View Condo
Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for relaxation and comfort. Located along the picturesque Wailea Blue Golf Course, this ground floor vacation rental offers breathtaking views of the lush...
Wailea Ekahi Village 38F - 2 Bedroom Ocean View Condo
Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui escape. This stunning two-bedroom, two-bathroom condo takes full advantage of its second floor positioning and boasts panoramic ocean views. Take...
Wailea Ekahi Village 19B - 2 Bedroom Ocean View Condo
Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to four guests. This beautifully designed residence features island-inspired décor, creating a cozy and inviting atmosphere perfect for families or...
Wailea Ekahi Village 11C - 2 Bedroom Garden View Condo
Wailea Ekahi 11C is an ideal Hawaiian retreat for friends or families traveling together. Each of the two bedrooms in this spacious condo feature a private lanai and en suite bathroom. Many guests return to this condo year after year for its close proximity to the pool...
Polo Beach Club 801 - 2 Bedroom Oceanfront Condo
Perched on the top floor, this vacation home offers breathtaking views and a touch of sophistication. The spacious kitchen, featuring a central island, provides ample room for culinary creativity while allowing you to enjoy the company of guests in the open living area....
Polo Beach Club 409 - 2 Bedroom Oceanfront Condo
Polo Beach Club 409 is a luxurious oceanfront vacation rental located in the world-renowned beach vacation destination of Wailea. This two-bedroom, two-bathroom condo offers a premium beachfront experience with direct access to Polo Beach out front and stunning ocean...
Polo Beach Club 407 - 2 Bedroom Oceanfront Condo
Polo Beach Club 407 is a premier oceanfront vacation rental located in the upscale resort area of Wailea. This two-bedroom, two-bathroom condo offers guests a luxurious and comfortable stay with sweeping ocean views and direct beach access out front. If looking for the...
Polo Beach Club 301 - 2 Bedroom Oceanfront Condo
Welcome to Polo Beach Club 301, a stunning third-floor corner residence that offers breathtaking views of Polo Beach. This spacious unit exemplifies the indoor-outdoor lifestyle that Hawaii is famous for, making it perfect for both entertaining and relaxing with friends...
Makena Surf F306 Beachfront Resort - 2 Bedroom Oceanfront Condo
Experience effortless mingling and entertaining in Makena Surf F306, where the open living area seamlessly connects to a spacious lanai. Enjoy the refreshing ocean breezes beneath the cathedral ceilings while taking in the stunning ocean views. This residence boasts...
Makena Surf F208 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf F208, a luxurious oceanfront vacation residence that offers an unparalleled Hawaiian retreat. Situated on the second floor, this 1,313 square foot residence is designed to provide the ultimate in comfort and relaxation, featuring elegant touches...
Makena Surf C207 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf C207, a vacation rental nestled in paradise. This spacious suite offers a serene escape, featuring two large lanais surrounded by the sweet scent of Plumeria. Unwind after a day at the beach by relaxing with friends and family, engage in a...
Makena Surf B106 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf B106, a stunning two-bedroom beachfront suite just steps away from the golden sands and the ocean\'s edge. This beautifully appointed residence combines luxury and comfort, featuring elegant tray ceilings, exquisite wood cabinetry, and...
Maui Banyan F-103 Stunning 2 Bedroom Condo With AC
**Please note: This is a ground floor unit, although there are stairs down from the parking lot and another set of stairs down to the ground floor hallway. Everything in the unit has been upgraded! Floors, newly built walk-in showers in both bathrooms, new bathroom...
Makolea#11: Steps from the Beach, Beautifully Appointed 2 bedroom condo
Island Living at Its Best – Remodeled 2BR/2BA Ground Floor Condo Steps from Kahaluu BeachWelcome to Unit #11 at Makolea Condominiums — your perfect Big Island getaway! This beautifully remodeled 2-bedroom, 2-bathroom ground-floor condo is tucked away in the heart of...
2 Bedroom Condo-Princeville, Kauai-Family Friendly!
Perched above the sparkling waters of Hanalei Bay, this resort offers families a front-row seat to some of Princeville’s most awe-inspiring natural beauty—from the dramatic Na Pali Cliffs and iconic Bali Hai Mountain to cascading waterfalls, golden beaches, and palm...
Gorgeous 5th Floor 2 Bedroom Condo. - Kihei Surfside #501
Kihei Surfside #501 – Top-Floor Oceanfront Views and Tranquility in a Rare 2-Bedroom LayoutWelcome to Kihei Surfside #501, a rare and spacious 2-bedroom, 2-bathroom oceanfront condo perched on the top floor of one of South Maui’s most sought-after properties. With...
Marriott's Waiohai Beach Club: New Years week: 2 Bedroom, full amenities
Experience the unparalleled magic of Hawaii at Marriott Waiohai Beach Club, a premium vacation ownership resort. Located by the ocean on Poipu Beach, we offer Kauai villa rentals and an array of resort amenities for your visit to the Garden Isle. Discover your family's...
Kailua Village#705 Top Floor, Gorgeous Remodeled 2 bedroom, in Heart of Town
Experience Paradise in This One of a Kind Stunning Two-Bedroom Penthouse in Downtown Kailua Kona, at the Famous Kailua Village. Escape to tropical bliss in this fully remodeled, top-floor(7th floor) penthouse located in the heart of Kailua Kona, Hawaii. With...
KAANAPALI COTTAGE 2 bedroom cottage within walking distance of Kaanapali Beach
International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres....
2 Bedroom Poipu Condo with Pool, Hot Tub walk to Beaches
Regency at Poipu Kai 911 is an air conditioned, ground floor suite located just steps to the pool. This 2-bedroom, 2-bath suite is great families and walking distance to the beach. This stunning condo has been upgraded throughout and is one of the few air-conditioned...
Makahuena Condo #1-304 - Modern Oceanview 2 Bedroom Condo With Pool
Step into the breezy, island-inspired comfort of Makahuena 1-304, where stunning ocean views and the charm of Kauai’s southern shore await you. This beautifully updated two-story condo offers 1,113 square feet of living space and includes 2 bedrooms and 2.5...
2 Bedroom Garden View - Maui Banyan #T108AB
Maui Banyan T108AB: With a functional floor plan and connecting door make this the ideal two-bedroom/two-bathroom ground floor unit for a family getaway. Exotic patterns and warm color tones set the mood while oversized windows allow for natural light and serene garden...
Wailea Ekolu 1207 2 Bedroom 2 Bath Condo
Relax at our quiet 2 bedroom /2 bath condo with stunning views overlooking the Wailea Blue golf course all the way to the ocean. Guests can enjoy amenities like a washing machine, AC, and WiFi during their stay. We hope you'll enjoy your stay at our condo.
Beachfront 2 Bedroom / 2 Bathroom Condo in Kihei
Indulge in luxurious island living at this oceanfront 2-bedroom, 2-bath condo in Kihei, Hawaii! This well-appointed condo is located directly on Keawakapu Beach, so you can spend your days splashing and snorkeling under the sun. Explore the excitement of the area at top...
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
FAMILY FUN at Pili Mai, 2br + Game room (bumper pool, poker table, classic video game console, board games, piano, masks and snorkels, beach chairs, croquet, bocce ball, spike ball, and small yard for the kids to play) 2.5 bath, sleeps 6, no stairs, back yard lawn....
2 bedroom home minutes to world class beaches, surf, scuba, snorkeling & golf!
Welcome to Puako Kai Hideaway, a beautifully updated vacation home in charming Puako. Located only minutes away from world class beaches, surf, scuba, snorkeling and golf. Extensive resort amenities, restaurants, shops and farmers markets are a short drive away.This...