Vacation rentals with a pool in Kihei

Silhouetted palm trees frame a golden sunset over the ocean, with the sun partially obscured by clouds. Gentle waves reflect the warm light, and grassy areas are visible in the foreground, contributing to a serene coastal scene.

4.96 out of 5 average rating, 187 reviews

Stunning Ocean Views -October Specials $174

*PLEASE NOTE A 14.8% HAWAII STATE TA/GE TAX WILL BE ADDED AND COLLECTED BY THE END OF YOUR STAY** COMPLETELY REMODELED THIS SUMMER IN A COMFORTABLE MODERN-TROPICAL STYLE. THE HIGHEST THREAD- COUNT LINENS AND TEAK THROUGHOUT THIS HIGH STYLED CONDO. HUGE VIEWS FROM THE MODERN KITCHEN, LIVING ROOM AND LANAI All SET IN THE HEART OF KIHEI. FABULOUS LOADS OF BEACH GEAR SURFING LESSONS DOWNSTAIRS BIKE RENTALS DOWNSTAIRS PARKS AND BEACHES ACROSS THE STREET 2 BLOCKS FROM SOME OF KIHEI'S FINEST RESTAURANT

4.99 out of 5 average rating, 124 reviews

The image captures a vibrant sunset over the ocean, with hues of orange, pink, and purple reflected across the water. Silhouetted palm trees line the foreground, adding a tropical feel. The landscape features rocky shorelines and gentle waves under the colorful sky.

Condo in Wailea

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and bi-coastal oceanfront views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (806) and includes two-bedroom suites on the world-famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent snorkeling, body surfing, whale watching, scuba diving, paddle boarding, and kayaking literally at your doorstep

An aerial view of a sandy beach is captured with gentle waves lapping at the shore. Shadows of palm trees stretch across the sand, creating a serene contrast against the turquoise water. The scene evokes a tranquil atmosphere, ideal for relaxation.

4.91 out of 5 average rating, 264 reviews

Gorgeous Getaway on the Beach

A freshly updated, fully-furnished condo situated across the street from the beach and nestled in a welcoming and quiet complex. Enjoy a beautiful space complete with a king-sized bed, renovated kitchen, a new sleeper sofa and a quiet lanai. With modern design and minimal decor, this space is perfect for you to unwind and relax. Complete with an in-unit washer and drier, this will be your home on the island and your oasis to rest. Steps away from food, drinks, a pool and the beach! Come stay!

An aerial view captures the coastal Menehune Shores complex, showcasing its resort-style architecture alongside the ocean. Lush green lawns extend towards the shore where gentle waves lap against the sandy beach. The backdrop features the expansive landscape of Maui, highlighting both land and sea.

4.99 out of 5 average rating, 123 reviews

Stylish Kihei Condo in Oceanfront Resort Complex

This 2 bed 2 bath home away from home offers everything you need for your Maui vacation and sleeps up to 6. Situated in the Hotel zoned oceanfront Menehune Shores complex, the condo is just steps to the beach and features an oceanfront pool, shuffleboard courts and acres of grassy lawn. Snorkel with the turtles in the ancient Hawaiian fishpond fronting the property or watch whales while you BBQ on the rooftop deck at sunset. The centrally located condo will have you never wanting to leave.

A modern kitchen is shown with sleek gray cabinetry and stainless steel appliances. An island seating area with two wooden stools is present, topped with a decorative tray and two cups. Pendant lights with blue shades illuminate the space, enhancing the open and functional layout.

4.96 out of 5 average rating, 179 reviews

Renovated Condo | 3 Min Walk to Toes in the Sand!

Welcome to Pacific Pearl — your serene Maui escape just steps from golden-sand Kamaole Beach Park II. Set in the lush, resort-style Maui Banyan complex, this fully remodeled ground-floor condo offers peaceful garden views, a walkable location near dining and shops, and all the comforts of home. Spend your mornings snorkeling, your afternoons lounging by the pool, and your evenings with sunset walks on the shore. Perfect for couples, families, or friends seeking the effortless Maui getaway.

5 out of 5 average rating, 119 reviews

An open and light-filled living area is featured, showcasing large glass sliding doors that offer views of lush tropical landscaping. A spacious gray sectional is complemented by a cozy chair, and a neutral area rug anchors the space. Decorative elements include the word "ALOHA" on the wall.

Condo in Wailea

*Tropical luxury at South Maui Surf Shack*

South Maui Surf Shack is located in Maui Kamaole. New renovations (Feb 2022) 1bed (King) 2bath + Murphy bed (Queen), beach style condo, over 1050 sq feet! Our fully stocked kitchen gives you the ability to cook your meals or head to any of the nearby restaurants in Kihei or Wailea (we are on the border). You are in the center of it all with the best beaches & golf courses Maui has to offer. We are here to help with absolutely anything you need to make your trip memorable, fun & relaxing!

A bright living area features sliding glass doors that open to a private lanai with ocean views. Comfortable seating options include a cozy sofa and armchair, complemented by a round coffee table and decorative pillows. Natural light fills the space, creating a welcoming ambiance.

4.98 out of 5 average rating, 138 reviews

Stunning Ocean Views · Steps to Beach · Comfort

Welcome to our slice of paradise in Maui and enjoy breathtaking 180° ocean views . Located just steps from the sandy Kamaole 1 Beach and a short stroll from vibrant restaurants and bars, our chic coastal-modern condo is the perfect spot for a beach getaway. Condo features all the amenities you need for a comfortable stay, including A/C in all rooms, a luxurious king bed, high-speed internet, fully equipped kitchen and a private lanai to watch sunsets. Your Maui adventure starts here

A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.

4.99 out of 5 average rating, 231 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

A private lanai offers a breathtaking view of the ocean and sandy beach. Two light-colored chairs with striped cushions are positioned around a small round table, accompanied by two glasses of water. Lush greenery and palm trees frame the serene setting.

5 out of 5 average rating, 174 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

SPECTACULAR OCEAN AND SUNSET VIEWS, including outer islands from the living room and lanai. You'll enjoy drinks in the evening watching the incredible sunsets. The condo has been totally redecorated and upgraded. The kitchen and bathroom have maple cabinets and elegant granite counter tops. There is a comfortable king size bed, a well-stocked kitchen, central AC, with all new bamboo floors throughout, and a new washer / dryer. The Condo is owned and maintained by Maui residents.

A spacious kitchen features modern white cabinetry and a large island with quartz countertops. Stainless steel appliances are visible, including an oven and refrigerator. The living area, partially seen in the background, includes a cozy couch and access to a balcony with views of lush greenery.

4.97 out of 5 average rating, 111 reviews

NEWLY remodeled Modern Maui condo across the beach

Enjoy a relaxing experience at this centrally-located Maui Vista condo, steps from popular Charley Young beach. Located in Building 2 with a nice breeze on the lanai overlooking lush lawn. Beautifully renovated (2021) modern design. This 1 bd 1 bath is located close to many shops and restaurants. Unit is on the 3rd floor (elevator access) w/luxury vinyl flooring. Stocked kitchen has everything you need w/ quartz countertops and large island. Stay cool with 2 AC units!

4.96 out of 5 average rating, 203 reviews

A dining table set for four is positioned on the private lanai, surrounded by lush greenery. A bottle of wine sits center stage, accompanied by a plate of fresh fruit and pastries. Bright blue skies provide a serene backdrop.

Condo in Wailea

Top 5% Home with King Bed + Steps to Beach & Shops

Exquisitely remodeled top floor condo in one of the most desirable condo complexes in South Maui. Enjoy sunsets and peekaboo ocean views from your private lanai, walk to some of the finest beaches, shops & restaurants and lounge in the multiple pools & hot tubs on property with this perfect Hawaiian oasis! Everything (and we mean everything) is fully remodeled. From a peaceful island getaway to your next Hawaiian adventure, Makana Condo is ready for your enjoyment!

The sleeping area features a spacious bed with a light-colored quilt and decorative pillows. Large sliding glass doors provide an expansive view of the ocean and palm trees, with soft curtains framing the scenic backdrop.