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.
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Premium Bay Villa | 2 Units, 2 Bedrooms | KBV ML-2008
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Premium Bay Villa | 2 Units, 2 Bedrooms | KBV ML-1981
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Large Master Suites | 2 Units, 2 Bedrooms | KBV ML-1984
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Premium Bay Villa | 2 Units, 2 Bedrooms | KBV ML-1960
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Large Master Suite | 2 Units, 2 Bedrooms | KBV ML-1966
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
NEW! Honua Kai | Free Rental Car | 2 Bedroom, 2 Bath Ocean View | Spacious Lanai | HKH-305
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Napili Point | 2 FREE Rental Cars | KBM Resorts | Water Front | 2 Units, 2 Bedrooms | NAP ML-2490
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kapalua Ridge Villas | 2 Free Rental Cars | KBM Resorts | 180 Degree Views! | 2 Units, 2 Bedrooms | KRV ML-2162
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
2 Bedroom Resort View - Platinum
Kaanapali Alii 3343 Bedrooms | 2 Bathrooms | Sleeps 8 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 334, a gorgeous 2-bedroom, ocean-view residence with a fully enclosed den that comfortably serves as a third bedroom. This...
Kaanapali Alii 2116
Welcome to Kaanapali Alii 2116, a luxury vacation rental nestled in the heart of Lahaina, Maui. This deluxe two-bedroom, two-bathroom condominium offers a serene escape with breathtaking views of the West Maui Mountains and lush greenery. Ideal for a family-friendly...
Kaanapali Alii 4113
Kaanapali Alii 41132 Bedroom | 2 Bathrooms | Sleeps 4 | Mountain View________________________________________Welcome to Kaanapali Alii 4113, a beautifully appointed one-bedroom mountain view residence with a fully enclosed den that comfortably serves as a second...
Makahuena 2-105 Ocean View 2 Bedroom 2 Bath, Sleeps 6, Ground Floor
Beautiful new renovation to this charming two bedroom 2 bath, ground floor condo. The living and dining areas are spacious and breezy, just steps from the pool. Generous kitchen for cooking fabulous meals, and the lanai looks out over the ocean with a great view of...
Waikiki 2 Bedroom - 2 Bath, washer/dryer in unit, full kitchen, free parking
PROPERTY OVERVIEW2-bedroom, 2-bathroom condo with fully equipped kitchen, in-unit washer/dryer, and a free assigned parking space. A second parking space is available upon request. Sliding doors allow natural trade winds to flow through the unit. High-floor location...
2 Bedroom Cottage - Platinum
Welcome to your tranquil haven at Cottage 2, nestled in the heart of Koloa. This charming 3-bedroom, 3-bathroom retreat offers a perfect blend of comfort and elegance, ideal for families or groups of friends. Each bedroom is equipped with a plush king-sized bed,...
The Lodge at Kukui‘ula - Bungalow 15
Step into the pinnacle of tropical luxury and comfort when vacationing in a two-bedroom bungalow at The Lodge at Kukui'ula on Kaua'i. Guests staying at Bungalow 15 enjoy privileged access to the esteemed amenities of The Club at Kukuiʻula. This exclusive enclave along...
The Lodge at Kukui‘ula - Bungalow 10
Indulge in the opulent comfort of the two-bedroom bungalows at The Lodge at Kukui‘ula on Kaua'i, offering privileged access to the esteemed amenities of The Club at Kukui'ula. This exclusive enclave along Kaua'i's southern coast boasts an 18-hole Tom Weiskopf designed...
The Lodge at Kukui‘ula - Bungalow 7
Bungalow 7 is a spacious ocean-view vacation home along Kaua'i's ideal southern coastline. It is the only two-story bungalow in our collection, offering commanding ocean views from the upstairs primary bedroom. This bungalow is conveniently within walking distance of...
The Lodge at Kukui‘ula - Bungalow 6
Welcome to Lodge at Kukui'ula Bungalow 6, a luxurious two-bedroom private retreat nestled on the pristine South Shore of Kauai. This idyllic bungalow offers the perfect blend of tranquility, modern comforts, and island charm. Designed with meticulous attention to...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | 180 Degree Views | 2 Units, 2 Bedrooms | KBV ML-1531
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
2 bedroom Waikiki Apt sleeps 6
This roomy apartment is perfect for a family or group. There are two separate bedrooms-both with queen sized beds. Both bedrooms also have a basic desk with chair which can also be used as a vanity table. The living room has a pull out queen size sofa bed. I have...
Whaler | 2 Free Rental Cars | KBM Resorts | Kaanapali Beach | 2 Units, 2 Bedrooms | WH ML-1580
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kapalua Golf Villas | 2 Free Rental Cars | KBM Resorts | Large Bedroom, Free Rental Car, Kapalua Golf Villas | 2 Units, 2 Bedrooms | KGV ML-1207
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Bali Hai Villas - 2 Bedroom Deluxe
Nestled high in the cliffs of Princeville, this Kauai resort blends natural and man-made pleasures into magnificent harmony. Take the opportunity to enjoy a meditative retreat at the on-site spa, or use the resort as a basecamp for your many Hawaiian adventures.NOTE:...
Kauai 2 Bedroom Villa Sleeps 8
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.The resort is beautifully landscaped with waterfalls and lagoons, lush tropical plants, and the sandy shores of Poipu Beach just steps away. While the beach is perfect for children, the...
Kona Hawaiian Resort 2 Bedroom w/ POOL
At Kona Hawaiian Resort in Kailua-Kona on the Big Island's west coast, you'll feel transported to a simpler, unspoiled era. Designed to evoke the charming traditional Hawaiian island ambiance of the 1930s, the resort blends nostalgic details with modern amenities and...
Wailea Point | 2301 - 2 Bedroom Ocean View Condo - 30+ Night Luxury Stays
Wailea Point is the ultimate in privacy and elegance for those seeking stays of 30 nights or longer. For shorter stays, please select from one of our other beautiful Wailea resort properties. The finest development in the finest neighborhood on the finest Hawaiian...
Wailea Grand Champions 52 - 2 Bedroom Garden View Condo
Welcome to your dream vacation in Wailea, Maui! This beautiful two-bedroom residence combines comfort, style, and convenience for an unforgettable stay in paradise. Upon entering, you\'ll be welcomed by a spacious, open living area, tastefully furnished for a relaxed...
Wailea Grand Champions 185 - 2 Bedroom Garden View Condo
This two-bedroom, two-bath villa at Wailea Grand Champions offers a perfect blend of contemporary style and tropical paradise. The open floor plan seamlessly connects the fully-equipped kitchen, dining area, and spacious living room, creating an inviting atmosphere for...
Wailea Grand Champions 140 - 2 Bedroom Garden View Condo
Wailea Grand Champions 140 is a remarkable vacation rental nestled in the upscale Wailea community of Maui. This charming property combines elegance with comfort, offering a luxurious retreat that is perfect for both relaxation and adventure. Upon entering Wailea Grand...
Wailea Grand Champions 102 - 2 Bedroom Golf Course View Condo
Welcome to Wailea Grand Champions 102, a luxurious 2-bedroom, 2-bathroom residence nestled between the fairways of one of Maui\'s most popular championship golf courses. This spacious second-floor unit, spanning over 1,400 square feet, offers a perfect blend of privacy...
Wailea Elua Village 707 - 2 Bedroom Ocean View Condo
Ideally situated in a quiet corner along the northern edge of the resort, Wailea Elua Village 707 is just a short stroll to the beachfront pavilion with swimming pool. This vacation rental in the heart of Wailea offers guests a comfortable and upgraded home which...
Wailea Beach Villas PH404 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1,978 sq. ft. of elegant indoor-outdoor living. Situated on the fourth floor, this penthouse enjoys sweeping views of the Pacific Ocean, Kaho\'olawe and...
Wailea Elua Village 706 - 2 Bedroom Ocean View Condo
Welcome to your dream vacation retreat in Wailea! As you step inside the newly renovated Wailea Elua 706, you\'ll immediately be captivated by the spacious and thoughtfully designed interior. The open concept living area is flooded with natural light, creating a warm...
Wailea Elua Village 2108 - 2 Bedroom Ocean View Condo
Welcome to Wailea Elua Village #2108. This two-bedroom, two-bath residence is fully remodeled and redecorated, features an extra-large floor plan of more than 1,500 square feet, and boasts gorgeous, elevated views of the ocean, off-shore islets, and lush tropical...
Wailea Beach Villas PH106 - 2 Bedroom Garden View Penthouse
Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui’s most prestigious beachfront communities. This stunning 1,899-square-foot villa offers the perfect blend of island elegance and modern comfort, making it an exceptional...
Wailea Elua Village 1510 - 2 Bedroom Ocean View Condo
Wailea Elua 1510 is a charming two-bedroom, two-bathroom vacation rental located in the premier Maui vacation destination of Wailea. This upstairs condo offers stunning ocean views and is just a short stroll away from the pristine Ulua Beach, one of the favorite...
Wailea Beach Villas PH104 - 2 Bedroom Garden View Penthouse
Marvel at the sophisticated style and décor of Wailea Beach Villas Penthouse 104, where a touch of Bali influence seamlessly merges with rustic undertones to create an unforgettable ambiance. The interior design captivates with elements like a textured wall-mounted...
Wailea Elua Village 1509 - 2 Bedroom Garden View Condo
Wailea Elua Village offers tropical vacation condos set amid Wailea’s resort hotels, making it a perfect luxury destination. Enjoy easy access from this vacation condo at Wailea Elua Village to the restaurants and spas of the Wailea resorts via the picturesque Wailea...
Wailea Elua Village 1504 - 2 Bedroom Ocean View Condo
Wailea Elua Village 1504 is a luxurious vacation rental located in the picturesque Wailea area of Maui. This beautifully designed two-bedroom, two-bathroom condo will check all the boxes your are looking for in your Maui vacation rental steps from the beach. The...
Makena Surf B204 Beachfront Resort - 2 Bedroom Oceanfront Condo
Experience the ultimate beachfront getaway at this luxurious 2-bedroom oceanfront vacation rental at Makena Surf, located on the stunning shores of Maui. This exquisite condominium offers breathtaking views of the Pacific Ocean and the nearby islands, including Molokini...
Makena Surf A204 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf A204 is a luxurious oceanfront residence offering a serene Hawaiian retreat. This spacious 1,600 square foot condo, located on the second floor, boasts breathtaking ocean views and direct access to the pristine Po\'olenalena Beach. The open-concept layout...
Kapalua Golf Villas | 2 Free Rental Cars | KBM Resorts | Large Bedrooms | 2 Units, 2 Bedrooms | KGV ML-2108
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Wyndham at Waikiki Beach Walk - Deluxe 2 Bedroom Condo
Located in Honolulu, Hawaii the Wyndham at Waikiki Beach Walk is just a short walk to a beautiful sandy beach and many great restaurants and shops including the Royal Hawaiian Shopping Center. Each of the units in this timeshare property feature a fully equipped...
Kihei 2 Bedroom Condo Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Located in South Maui, nestled within five acres of lush tropical landscaping. This low-density complex features amenities such as a large swimming pool, hot tub, tennis and pickleball...
Monthly- Chateau Waikiki 3513 2 Bedroom Ocean / Diamond Head
PANORAMIC OCEAN / Diamond Head VIEWS, 10 Minute Walk to Beach, 2 Bed Room, Furnished. No smoking condo. 2 Parking, Pool, Utilities, WIFI, BBQ, Gym, Security, Washer/Dryer Included. 2 Month Minimum / contact Agent.Spectacular ocean, volcano, mountain and town views from...
Napili Point | 2 Free Rental Cars | KBM Resorts | Ocean View 1-bedroom Villa At Napili Point Maui | 2 Units, 2 Bedrooms | NAP ML-1559
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Napili Point | 2 Free Rental Cars | KBM Resorts | Ocean View 1-bedroom Villa At Napili Point Maui | 2 Units, 2 Bedrooms | NAP ML-1547
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kanai A Nalu 416 Oceanfront 2 bedroom Overlooking South Maui Ocean
Book with us and come to Maui to explore everything we have to offer!Enjoy the ocean breeze in your luxury 2 bedroom/2 bath condo home. Wander right out to the beach. The split air-conditioned unit is fully equipped, including an in-unit washer/dryer. The primary...
Napili Point | 2 Free Rental Cars | KBM Resorts | Ocean View 1-bedroom Villa At Napili Point Maui | 2 Units, 2 Bedrooms | NAP ML-1553
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Grand Champions | 2 Free Rental Cars | KBM Resorts | Extra Large Corner Suite | 2 Units, 2 Bedrooms | ML-1493
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...