Hawaii Vacation Rentals » Hawaii Vacation Rentals Discounts and Specials

Hawaii Vacation Rentals Discounts and Specials

Unlock exceptional savings on your next island escape with exclusive Hawaii Vacation Rentals Discounts and Specials. From oceanfront condos in Kihei to designer homes in Princeville, these curated deals offer luxury accommodations at unbeatable rates. Enjoy amenities like private pools, gourmet kitchens, and stunning ocean views, all while benefiting from seasonal promotions and limited-time offers. Whether you're planning a romantic getaway or a family vacation, these specials provide the perfect opportunity to experience Hawaii's beauty without compromising on comfort or budget.

Take advantage of these Hawaii Vacation Rentals Discounts and Specials to explore the islands' diverse landscapes and attractions. With properties available across Maui, Oahu, Kauai, and the Big Island, you can find the ideal home base for your adventures. Don't miss out on these limited-time offers—book now to secure your dream vacation rental at a fraction of the regular price.

Sort By

It's Special - This Award Winning Designer Masterpiece is Phenomenal!

Kauai Haven is nestled within a classic Hawaiian style backdrop, resting on the edge of a bluff overlooking the spectacular Pacific Ocean. An award-winning designer, who is part of the Coastal Living Network of designers, has designed this

2 bedroom
2 bathroom
Sleeps 4

from $566

View Property

Makai Hideaway 600ft from Ocean Giant Deck/GameroomnAsk about 10 day special

Ask about 10 day specials/ 2 person stays and 8th night free if you book a 7th night stay!!!!
https://www.youtube.com/watch?v=VigSB3M4z3w
The above is the link to a video of my house.
Makai Hideaway is quiet and peaceful. Unwind and

3 bedroom
3 bathroom
Sleeps 10

from $295

View Property

100% OCEAN VIEWS FROM ALL ROOMS, Cancellation June Special!!, Hokulani #525

**A guest cancelled and our misfortune is your opportunity to book a great deal... book any dates (6 night minimum) from June 5th -June 16th 2025 for $995/night. Book one more night and receive an even better deal with our 7 night

4 bedroom
3 bathroom
Sleeps 8

from $1,163

View Property

MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage

Maui Permit #BBPH 2009/0002 , Hawaii Permit #SUP2 2002/0005
Hawaii Tax I.D. TA035-442-8928-01 TMK (2)2-7-035-010-0000
Maui's Ultimate Private, Romantic Cottage! ...a unique architectural Polynesian Pole home on Magical Maui.

1 bedroom
1 bathroom
Sleeps 2

from $487

View Property

April Special 199/night! Honomū Haven - At the Gateway to Akaka Falls 🏝

Aloha and welcome to Honomū Haven!

Our home is located in the quaint & charming town of Honomū, just 13 miles north of Hilo and 3 miles from 'Akaka Falls on the Big Island of Hawaii. This 5 bedroom, 2 bathroom home was meticulously

5 bedroom
2 bathroom
Sleeps 10

from $341

View Property

Special 1/12-3/9/25! Beachfront, 1 BR/1BA apartment. Steps away from the ocean!

Located in central Kihei, nestled in on the northern end of beautiful Halama Street. Family-owned and operated legal short-term rental. This ocean front, 1 bedroom 1 bath unit, has a full kitchen and bathroom. Cozy, quiet, great for couples and

1 bedroom
1 bathroom
Sleeps 3

from $354

View Property

ONLY $129 ...... LUXURY CONDO SPECIAL TOTAL REMODEL Bldg 1

OCEAN VIEW

BOOK WITH US TODAY!

BEST REMODEL in MAUI VISTA

Completely gutted with NEW EVERYTHING!!!

Tigerwood Hardwood Floors, Italian Tile, Travertine, Fresh Paint, Ceiling Fans, All New Furniture, New Mattress

1 bedroom
1 bathroom
Sleeps 2

from $306

View Property

Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views

This eco-friendly home is powered from the grid using net metering with 10 KW solar on the roof and is surrounded by 2 acres of organic orchard of mangoes, avos, figs, citrus, papayas and tropical fruits. Solar carport sports a charger for an

3 bedroom
3 bathroom
Sleeps 6

from $808

View Property

Beachfront Condo B303 May 10-15 available at special rate of 750 per night

Relax and enjoy panoramic views and beachfront perfection. The 2 bedroom, 2 bath home is located in the B building and sits only steps from an extraordinary sandy beach offering the famous 'five island view' along with the accompanying

2 bedroom
2 bathroom
Sleeps 4

from $1,097

View Property

A Perfect Kapalua Beach and Golf Getaway - Specials!!!

Come enjoy our spacious 1 bedroom, 2 bathroom condo in one of the most beautiful spots in all of Maui. Located directly on the 4th fairway of the Kapalua Bay Course can be both entertaining and comical as you watch the golfers pass by. A

2 bedroom
2 bathroom
Sleeps 4

from $408

View Property

SPECIAL LOW RATES- Spacious Studio-5 stars-Amazing Lanai with ocean view

HONUA KAI RESORT AND SPA SUITE 215 welcomes you with so much ALOHA....

This spacious studio unit with full bath can accommodate up to 4 guests.

Included in our fabulous price are many owner-supplied extras such as:
• Beach

1 bedroom
1 bathroom
Sleeps 4

from $416

View Property

Special Rates! Lush Garden Views! Maui Banyan H205

Your dream vacation awaits you on the Island of Maui in this beautifully upgraded condominium located across the street from Kamaole II Beach Park. Surrounded by lush tropical landscape, Maui Banyan is just steps away from restaurants, shops,

2 bedroom
2 bathroom
Sleeps 4

from $277

View Property

WOW!!! Great Winter Special Minutes from the Beach. NEW AC for your Perfect Stay

Top to bottom fully renovated 2 bdr 2 bath 1244 sq ft condominium in Maui Kamaole. Largest floor plan in the complex.

Enjoy ocean views and the quiet location of our unit located in the D Cluster of Maui Kamaole.

Tastefully

2 bedroom
2 bathroom
Sleeps 4

from $398

View Property

SPECIAL RATE! 5/11/25 to 5/16/25 1,150 per nightnLOCATION! LOCATION! LOCATION!

Hale Halia is just steps from Poipu Beach park with unparalleled oceanfront views and is a great family vacation destination. This lovely two-story floor plan is a design that takes full advantage of the magnificent Poipu coastline and sunset

4 bedroom
3 bathroom
Sleeps 10

from $1,548

View Property

New May Specials, 5 Star Reviews! F403 Top Floor 2 BR/3 BA

Welcome to the Waipouli Beach Resort and Spa! The premier resort on Kauai!

Waipouli Beach Resort and Spa is located beach front on the Coconut Coast between the historic towns of Kapaa and Wailua. Located convenient to both Princeville

3 bedroom
3 bathroom
Sleeps 6

from $679

View Property

- Luxury Vacationing Modern Condo - Spring Specials -299 USD-

***The pool has just been renovated and is gorgeous beginning November 1st 2024***JUST RENOVATED DESIGNED BY A NYC ARTIST. THIS BEAUTIFUL CONDOMINIUM IS BORDERING KIHEI AND WAILEA IN SOUTH MAUI, HAWAII. IT IS LOCATED AT THE GORGEOUS MAUI HILL

3 bedroom
2 bathroom
Sleeps 6

from $476

View Property

🤙 APRIL+May Request SPECIAL 🏝️ at the upgraded LIVE ALOHA SUITE

Receive a discountfrom the listed price by contacting me through VRBO! THE LIVE ALOHA SUITE is a tastefully designed condo by Stannard Architects, of an international design firm, Olson Sundberg. It is a reflection of the tropics, well

1 bedroom
1 bathroom
Sleeps 4

from $605

View Property

KULALANI 904 ~ SPECIAL RATES & DINE ON US LAVA LAVA BEACH CLUB!!

$350/NT+TAX SPECIAL PLUS $100 LAVA LAVA BEACH CLUB CARDS FOR A LIMITED TIME!

UNBELIEVABLE SPACIOUS TOWNHOME ILLUMINATED WITH A WALL OF NATURAL LIGHT!

Kulalani 904 is one of the newest homes developed within the resort. At a

2 bedroom
3 bathroom
Sleeps 4

from $522

View Property

Take advantage of our SUMMER SPECIAL DISOUNTS on this beautiful property

SEE OUR SUMMER SPECIAL
This is the perfect SUITE located in the east of the property for an outdoor lover who wants to feel the connection with nature and enjoy of an amazing

1 bedroom
1 bathroom
Sleeps 2

from $290

View Property

Take advantage of our SUMMER SPECIAL DISOUNTS on this beautiful property

CHECK OUR SUMMER SPECIALS
you could consider the West suite a little more private with the kitchen area inside but You will also hear the waves crashing. See the turtles in front of your vacation Suite. Enjoy the

1 bedroom
1 bathroom
Sleeps 2

from $290

View Property

SPRING SPECIAL! See Our Location!..Read Our Reviews!..So Many Extras!

Our 'home away from home' townhome is the perfect place to enjoy your vacation! It is luxuriously decorated with top of the line furnishings and orginal art work, yet extremely comfortable and welcoming. Since our townhome is NOT a full-time

2 bedroom
3 bathroom
Sleeps 5

from $405

View Property

WORLD CLASS Special May Disc 13-18 & 25 to 6-1. Full AC, 2 Suites 550

Spectacular views from high on top of the cliffs of Princeville. This top-level condominium is terraced at the edge of the bluff, commanding unobstructed blue Pacific Ocean views, including Hanalei Bay. Easterly trade winds caress the property

2 bedroom
2 bathroom
Sleeps 4

from $805

View Property

Nihi Kai 422 Summer & Fall Specials-Ocean Views, Five Star Ratings!

OFFERING DISCOUNTS FOR FALL 2025 !!

This large 1400 square-foot, two-bedroom, single level, beautifully furnished condo has spectacular ocean views from the front lanai, living room, master bedroom, and kitchen. This third-floor unit has

3 bedroom
2 bathroom
Sleeps 6

from $505

View Property

Special ~ Kapalua Golf Villa 24T8 - 1BD Luxury

SPRING SPECIAL!
Kapalua Golf Villa 24T8 – Ocean View Elegance at Its Finest

Indulge in the tranquil beauty of Maui at Kapalua Golf Villa 24T8, a beautifully appointed 1-bedroom, 2-bathroom villa that perfectly blends luxury, comfort,

2 bedroom
2 bathroom
Sleeps 4

from $333

View Property

Summer Special! 10% Discount With 7 Day Stay

Nestled in the heart of Waikoloa Villas, this top-floor 2 bedroom/2 bath condo offers serene views overlooking the Waikoloa Village golf course. Just a short drive away, you'll find the island's best beaches at Waikoloa Beach Resort, along with

2 bedroom
2 bathroom
Sleeps 4

from $327

View Property

'Best Vacation Ever' Say Our Guests! Special May Rates

You will love this luxurious, air conditioned, two bedroom, two bath, 1300 square foot Villa! Fully furnished, with its own spacious, private dining lanai, this unit was completely remodeled in 2020. It is immaculate, impeccably maintained and

2 bedroom
2 bathroom
Sleeps 6

from $440

View Property

Sunset Beach House in paradise! Inquire for special 30 day rates!

Unit B1 is Ocean Front at Sunset Hale. Newly updated 2-bedroom 2.5-bath ground floor oceanfront unit.
The Kitchen, living room and dining area are all facing out to beautiful ocean and sunset views! Enjoy these views from inside or

2 bedroom
2 bathroom
Sleeps 5

from $952

View Property

Beautiful 2bd/2bth Wailea Grand Champions Condo- Special Rates!

Our beautifully appointed condo is perfect for a family (6 maximum), a couple or two couples (as there are 2 primary bedroom suites, each with a king size bed, private bath and flatscreen ). The condo features a spacious living and dining area

2 bedroom
2 bathroom
Sleeps 6

from $511

View Property

Spectacular Beach Resort Condo - Summer Special - Amazing Views

You will love how close we are to the beaches, shopping, restaurants and central to travel and hiking spots and hidden gems. This second floor 2 bed 2 bath unit has phenomenal mountain views with peak a bay ocean view and located on the Kings

2 bedroom
2 bathroom
Sleeps 5

from $389

View Property

SPRING BREAK SPECIAL! Lau'eki Estate ~ Hualalai ~ Sweeping Views ~ Infinity pool

Welcome to your tranquil oasis at the exclusive Lalani Lau'eki Estate at the Four Seasons Hualalai Resort. This private estate is nestled between exquisite and expansive ocean and Hualalai mountain views—perfect for beautiful Hawaiian

4 bedroom
5 bathroom
Sleeps 8

from $5,241

View Property

5-star and rave reviews. Amazing views. Newly furnished. Specials for April/May!

SPECIAL RATES for April/May!

Relax in what feels like your open-air home in paradise!

Stunning views. Savor the outside air and breezes on your lanai. Superbly maintained. Consistent rave reviews (for years as we are original

3 bedroom
3 bathroom
Sleeps 8

from $1,190

View Property

SPRING BREAK SPECIAL!! Waiulu Tropical Sanctuary ~ Hualalai

Welcome to the exclusive Waiulu Tropical Sanctuary resting within the Hualalai Resort. Be one of the first to enjoy stunning contemporary interiors completed masterfully by the renowned Henderson Design Group. Every detail has been

4 bedroom
5 bathroom
Sleeps 8

from $5,949

View Property

Haleiwa oceanfront inquiry special rate options

Discover the delightful onebedroom getaway nestled right within Haleiwa. Nestled just a 22-minute drive from the renowned Banzai Pipeline and 24 minutes from the stunning Turtle Bay Beach, this cozy retreat offers the perfect base for your

1 bedroom
1 bathroom
Sleeps 3

from $556

View Property

Last minute special 180 from 7/1/24-7/31/24! nCome and enjoy Aloooooohaa!!

Yes you can afford this great vacation in our wonderful condo, located near Wailea . We are in the Hale Kamaole resort and are on the ground floor.
Features include:
1. Walking distance to Kamaole Beach 3 (it's right across the street :)

1 bedroom
1 bathroom
Sleeps 4

from $325

View Property

Summer Special Gorgeous Golf Course and Ocean Views Luxury Living Private Pool and Spa Mauna Lani Resort Includes 6 person Golf Cart

Enjoy the splendor of this Luxury 2 story townhome, at the exclusive Residences of Laulea located within the world class Mauna Lani Resort.

This Luxury residence is designed for comfort and serenity. The main level of this property offers

4 bedroom
5 bathroom
Sleeps 8

from $2,005

View Property

LUXURY OCEANFRONT MAKENA SURF - 3 BR/3 BA - CONTACT OWNER FOR SPECIAL RATE

Welcome to the newly renovated, top floor ''Turquoise Cove'' Villa - Makena Surf F301. This amazing property has unsurpassed ocean views, with a unique, double wrap-around lanai, perfect for enjoying tropical sunsets or catching the occasional

3 bedroom
3 bathroom
Sleeps 8

from $1,750

View Property

Spring Special! Live Inspired! Live Kapalua Beautiful Villa! – No Resort Fees

Step into luxury island living at this beautifully upgraded one-level, two-bedroom Golf Villa in the heart of Kapalua Resort. From the moment you walk through the door, pride of ownership is evident in every detail. This corner location villa

2 bedroom
2 bathroom
Sleeps 6

from $570

View Property

SPECIAL!!! Christmas week @ Westin Ocean Villas N, 2 BR Ocean View, by Owner

First, to see pictures of the rooms, please go to the vistana website. Google THE WESTIN KĀ‘ANAPALI OCEAN RESORT VILLAS NORTH. Then look up TWO-BEDROOM LOCKOUT VILLA. They have tons of photos, better than we can take.

This area is

3 bedroom
2 bathroom
Sleeps 8

from $1,769

View Property

Large End Unit - Special Pricing - Luxurious 3 Bedroom/3 Bath Town Home

This beautiful 1850 square foot 3 bedroom / 3 bath town home is a very private end unit which has a wall of windows that fill the living area with natural light. On the main floor, you will find a gourmet kitchen with granite counter tops and

3 bedroom
3 bathroom
Sleeps 7

from $657

View Property

MAUI OCEAN Beach FRONT AMAZING VIEWS Summer special 275 nightly

Our beautiful condo is located on the world famous Kaanapali Beach and shores. You can't get any closer to the ocean then the MAUI KAI Resort, the Bldg. Is just feet away with the best snorkeling right outside the front door. As you relax on

1 bedroom
1 bathroom
Sleeps 4

from $341

View Property

Ocean View Studio #264 - May 11-19, 2025 - Special

**Spring to Maui **Special

May 11-19, 2025 Available
$250 + tax p/n
5 night minimum required

** No Host Fee EVER **

Located on pristine Kaanapali Beach, the Whaler is truly a spot of absolute paradise; no other

1 bedroom
1 bathroom
Sleeps 2

from $324

View Property

SUMMER SPECIAL! AMAZING VIEW! Book Between May 25th - Aug 31 375/night!

Breathtaking views from our Unit 507 at The Whaler on Kaanapali Beach. 1 back from oceanfront! 1 bedroom unit has a king sized bed and a full size Murphy bed. 2 full baths. Sleeps 4 comfortably. Also a well equipped full

1 bedroom
2 bathroom
Sleeps 4

from $481

View Property

SPRING SPECIAL Fairway Villas : Golf View-AC- 2br - Golf Discount

Aloha and welcome to our Hale Okakopa, Fairway Villas A22 in the Waikoloa Beach Resort. Each room features its own treasures: from intuitive Sapele built-ins like the kitchen desk and entry bench, to the tropical elegance of the primary

2 bedroom
2 bathroom
Sleeps 4

from $355

View Property

There is NO PLACE like Wailea especially in a two-storey townhouse! Enjoy!

WELCOME TO OUR HAWAIIAN RETREAT in Wailea!
We purchased our second property in Wailea - November 2019. Enjoy your getaway at our new home-away from home! We spent the 2019 holiday season buying new furniture for EVERY room, decorating,

2 bedroom
3 bathroom
Sleeps 6

from $417

View Property

Steps to Kahana Beach from this fully remodeled condo - Listing Special 40% OFF

Welcome to @Maui Makai Condo!

This lovely 1 bedroom, 1 bathroom condo is situated in the hotel zone and just a stone's throw away from Kahana Beach in West Maui (conveniently nestled between Ka'anapali and Kapalua).

Following

1 bedroom
1 bathroom
Sleeps 4

from $261

View Property

Next Generation / Remodeled-2 Bedroom-2 Full Bath-End Unit-Specials!

Magnificent large 7th floor end unit condo, considered the corner suite, is fully equipped with new furnishings, including barn doors, new ceilings, new bathrooms, new kitchen, new flooring and ultra modern features throughout. This condo has

3 bedroom
2 bathroom
Sleeps 6

from $422

View Property

Papakea Paradise, G102, 2 Bedroom & 2 Bathroom, Ground Level, Air Con, Specials!

The much coveted ground floor, one level, 2 bedroom - 2 bathroom floor plan at Papakea. No steps! Also, brand new ductless air conditioning system in both bedrooms and living room / kitchen area. An amenity not all of the condos have! Enjoy

2 bedroom
2 bathroom
Sleeps 6

from $402

View Property

Special Rate 1/12/25-3/9/25! Escape to our Cozy 2 BR/1BA COTTAGE in Kihei!

Located in central Kihei, nestled on the northern end of beautiful Halama Street. Family-owned and operated legal short-term rental. A cozy 2 bedroom, 1 bath cottage with a large deck for sunbathing or BBQS. Less than a three-minute walk on the

2 bedroom
1 bathroom
Sleeps 4

from $462

View Property

Relax in the Kapalua Golf Villas - Listing newly back on the market - Specials!

Relax in paradise! Top floor condo with a one level floor plan. All new furnishings, carpet and paint. Lovely lanai to watch the golfers go by and enjoy the views and smells of the island of Maui. There are 4 pools in the Kapalua Golf

1 bedroom
2 bathroom
Sleeps 4

from $310

View Property

Kolea 3B - Special Rates Plus Lava Lava Beach Club!!

Kolea 3B Special Rate $550/nt+tax Plus $100 Lava Lava Beach Club for a limited time!

3 bedroom, 3.5 bath
2nd floor level with semi private elevator
Partial ocean and mountain views
Master suite king bed with private lanai,

3 bedroom
4 bathroom
Sleeps 6

from $861

View Property

Showing 1 of 5 pages.