Hawaii Vacation Homes and Villas with Pools

a view of the ocean with a red bus on the beach at Direct Oceanview Paradise in a luxury condo 2B2B,AC in Kailua-Kona

From US $494

Direct Oceanview Paradise in a luxury condo 2B2B,AC Pool available

8.3 (59 Reviews) Villa

The entire place is yours • 186 m² size • Free on-site parking

Best Price Match

a bedroom with a bed and a living room at Tiki Tiki - Gorgeous Boho Beach Hideaway! in Wailea

From US $402

Tiki Tiki - Gorgeous Boho Beach Hideaway! Pool available

9.5 (35 Reviews) Apartment

The entire place is yours • 34 m² size • Swimming pool

Best Price Match

a house with a swimming pool next to the ocean at Unobstructed Ocean Views, AC, Pool, Spa, 5 mins Beach, 2B2B, Sleeps 6 in Kailua-Kona

From US $396

Unobstructed Ocean Views, AC, Pool, Spa, 5 mins Beach, 2B2B, Sleeps 6 Pool available

8.8 (44 Reviews) Apartment

The entire place is yours • 93 m² size • Kitchen

Best Price Match

a kitchen with a table and chairs and a couch at Aloha Moon - A Chic and Dreamy Modern Tropical Hideaway! in Wailea

From US $494

Aloha Moon - A Chic and Dreamy Modern Tropical Hideaway! Pool available

9.9 (27 Reviews) Apartment

The entire place is yours • 73 m² size • Kitchen

Best Price Match

a view of the ocean from the beach at Maui Vista - Kihei Kai Nani Beach Condos in Kihei

From US $318

Maui Vista - Kihei Kai Nani Beach Condos Pool available

8.0 (39 Reviews) Apartment

The entire place is yours • 59 m² size • Free on-site parking

Best Price Match

a bedroom with a bed and a sink and a mirror at WAIKIKI 2 BEDROOMS, 1 BATH, FREE PARKING, SLEEP 6 in Honolulu

From US $610

WAIKIKI 2 BEDROOMS, 1 BATH, FREE PARKING, SLEEP 6 Pool available

9.8 (29 Reviews) Apartment

The entire place is yours • 67 m² size • Free private parking

Honolulu Waikiki Beach Walk

Best Price Match

an aerial view of a beach and the ocean at Direct oceanfront Magic Sands beach condo - Pool, AC, 2B2B, sleeps 6 in Kailua-Kona

From US $422

Direct oceanfront Magic Sands beach condo - Pool, AC, 2B2B, sleeps 6 Pool available

8.6 (31 Reviews) Holiday_home

The entire place is yours • 121 m² size • Free on-site parking

Best Price Match

a dining room with a table and chairs on a balcony at Kona Designer Condo l Pool l Near Beach l AC l Free Parking l Sleeps 6 in Kailua-Kona

From US $518

Kona Designer Condo l Pool l Near Beach l AC l Free Parking l Sleeps 6 Pool available

9.7 (18 Reviews) Apartment

The entire place is yours • 111 m² size • Kitchen

Best Price Match

a swimming pool with a stone floor and a patio at Signature Residences at Maui Banyan, Walk to Beach, Limited Offer in Wailea

From US $458

Signature Residences at Maui Banyan, Walk to Beach, Limited Offer Pool available

8.1 (24 Reviews) Apartment

Apartments • Free on-site parking • Outdoor swimming pool

Best Price Match

a balcony with a view of the ocean at Gorgeous Blue Ocean Views, AC, Sunsets & 1-Min Walk to Beach in Kailua-Kona

From US $389

Gorgeous Blue Ocean Views, AC, Sunsets & 1-Min Walk to Beach Pool available

8.9 (27 Reviews) Apartment

The entire place is yours • 74 m² size • Free on-site parking

Best Price Match

a bathroom with a shower and a toilet and a sink at Kihei Kai Nani Resort in Kihei

From US $300

Kihei Kai Nani Resort Pool available

8.0 (23 Reviews) Apartment

The entire place is yours • 60 m² size • Free on-site parking

Best Price Match

a white beach with the ocean and blue sky at Kihei Beach Paradise Steps to Sun, Sand & Snorkeling in Kihei

From US $343

Kihei Beach Paradise Steps to Sun, Sand & Snorkeling Pool available

8.5 (18 Reviews) Apartment

The entire place is yours • 59 m² size • Free private parking

Best Price Match

a swimming pool with a sunset in the background at Affordable Luxury on One Acre in Kailua-Kona

From US $603

Affordable Luxury on One Acre Pool available

10.0 (7 Reviews) Villa

The entire place is yours • 111 m² size • Free on-site parking

Kalaoa Ellison Onizuka Kona International Airport

Best Price Match

a balcony with a view of the ocean at Makena Surf G303, Maui on the Beach in Wailea

From US $870

Makena Surf G303, Maui on the Beach Pool available

9.5 (8 Reviews) Apartment

The entire place is yours • 96 m² size • Free on-site parking

Best Price Match

a living room with a red wall at Hawaiian Escape with Pool Expansive Lanai Stunning Sunset Views in Kailua-Kona

From US $855

Hawaiian Escape with Pool Expansive Lanai Stunning Sunset Views Pool available

10.0 (9 Reviews) Villa

The entire place is yours • 325 m² size • Free on-site parking

Best Price Match

a living room with a table and chairs at Signature Stay at Kamaole Sands Resort, Walk to Beach, Limited-Time Offer in Wailea

From US $502

Signature Stay at Kamaole Sands Resort, Walk to Beach, Limited-Time Offer Pool available

8.9 (7 Reviews) Apartment

Apartments • Free on-site parking • Outdoor swimming pool

Best Price Match

a bedroom with a bed and a ceiling fan at Premier Collection at Grand Champions Wailea - Limited-Time Half Off in Wailea

From US $414

Premier Collection at Grand Champions Wailea - Limited-Time Half Off Pool available

7.4 (16 Reviews) Apartment

Apartments • Free on-site parking • Outdoor swimming pool

Best Price Match

an aerial view of a resort on the ocean at Royal Sea Cliff Kona by OUTRIGGER - Select Your Unit in Kailua-Kona

From US $527

Royal Sea Cliff Kona by OUTRIGGER - Select Your Unit Pool available

8.0 (13 Reviews) Apartment

Apartments • Kitchen • Sea view

Best Price Match

a group of palm trees in front of a sunset at Wailea Sunset Condo - Ekolu #607 in Wailea

From US $408

Wailea Sunset Condo - Ekolu #607 Pool available

9.2 (7 Reviews) Holiday_home

The entire place is yours • 95 m² size • Free on-site parking

Best Price Match

a balcony with a view of the ocean and palm trees at Wailea Elua Village on Ulua Beach in Wailea

From US $1400

Wailea Elua Village on Ulua Beach Pool available

9.6 (5 Reviews) Apartment

The entire place is yours • 111 m² size • Free on-site parking

Best Price Match

a group of people sitting on a beach at Amazing Kihei Kai Nani - Maui Vista One Bedroom Condos in Kihei

From US $305

Amazing Kihei Kai Nani - Maui Vista One Bedroom Condos Pool available

7.1 (15 Reviews) Apartment

The entire place is yours • 59 m² size • Free on-site parking

Best Price Match

a view of the ocean from the balcony of a house at Wailea Elua Resort 1904 in Wailea

From US $1400

Wailea Elua Resort 1904 Pool available

10.0 (3 Reviews) Apartment

The entire place is yours • 127 m² size • Outdoor swimming pool

Best Price Match

an overhead view of a swimming pool with chairs and the ocean at Kailua-Kona Exceptional Oceanview Home - Heated Oasis Pool & Stunning Ocean View in Kailua-Kona

From US $599

Kailua-Kona Exceptional Oceanview Home - Heated Oasis Pool & Stunning Ocean View Pool available

8.3 (6 Reviews) Holiday_home

The entire place is yours • 207 m² size • Kitchen

Best Price Match

a woman sitting on a balcony looking out at the ocean at Panoramic Oceanview Resort - Full Kitchen in Each Unit, 2 Swimming Pools, Onsite Restaurants, Fireworks Every Friday in Honolulu

From US $367

Panoramic Oceanview Resort - Full Kitchen in Each Unit, 2 Swimming Pools, Onsite Restaurants, Fireworks Every Friday Pool available

9.0 (164 Reviews) Apartment

Apartments • Private parking • 2 swimming pools

Honolulu Waikiki Beach Walk

Best Price Match

a camper van parked on a beach with people at Kona Magic Honu Room in Kailua-Kona

From US $161

Kona Magic Honu Room Pool available

9.4 (290 Reviews) Homestay

Free on-site parking • Outdoor swimming pool • Balcony

Best Price Match

a hotel room with two beds and a mirror at soulfactory Hawaii in Honolulu

From US $130

soulfactory Hawaii Pool available

7.5 (135 Reviews) Apartment

Apartments • Private parking • Outdoor swimming pool

Honolulu International Market Place

Best Price Match

a green and white sign for a vitz clinic at Enjoy the sunset at OCEAN FRONT 1BR Apartment - pool on site! in Kailua-Kona

From US $278

Enjoy the sunset at OCEAN FRONT 1BR Apartment - pool on site! Pool available

8.4 (94 Reviews) Apartment

Apartments • Free on-site parking • Outdoor swimming pool

Best Price Match

a living room with a table and chairs and a kitchen at Maui Kamaole B207 in Wailea

From US $427

Maui Kamaole B207 Pool available

9.6 (47 Reviews) Apartment

The entire place is yours • 104 m² size • Kitchen

Best Price Match

a living room with a couch and a coffee table at Beautiful 2 Bedroom Oceanview Condo at Maui Kamaole Located at South End of Kihei Adjacent to Wailea Traditional Hawaiian Style in Wailea

From US $359

Beautiful 2 Bedroom Oceanview Condo at Maui Kamaole Located at South End of Kihei Adjacent to Wailea Traditional Hawaiian Style Pool available

9.6 (45 Reviews) Apartment

The entire place is yours • 119 m² size • Free on-site parking

Best Price Match

a group of people sitting on a wall watching the sunset at Unrivaled S Kihei Maui location! Walk to it all! in Kihei

From US $287

Unrivaled S Kihei Maui location! Walk to it all! Pool available

9.6 (45 Reviews) Apartment

The entire place is yours • 58 m² size • Free on-site parking

Best Price Match

a swimming pool at a resort with palm trees at Maui Kamaole in Wailea

From US $369

Maui Kamaole Pool available

8.0 (80 Reviews) Apartment

Apartments • Outdoor swimming pool • Balcony

Best Price Match

a table with a view of the ocean and palm trees at Enjoy Your Oceanside Dream at Kihei Surfside in Wailea

From US $288

Enjoy Your Oceanside Dream at Kihei Surfside Pool available

9.4 (37 Reviews) Holiday_home

The entire place is yours • 47 m² size • Kitchen

Best Price Match

a living room with a couch and a table at Amazing View Waikiki Beach 28th Floor 1BR Family and Group Condo in Honolulu

From US $291

Amazing View Waikiki Beach 28th Floor 1BR Family and Group Condo Pool available

9.3 (37 Reviews) Apartment

The entire place is yours • 63 m² size • Private parking

Honolulu International Market Place

Best Price Match

a kitchen with a sink and a view of the ocean at Ocean View 2 Bedroom Kahalu'u Reef in Kailua-Kona

From US $401

Ocean View 2 Bedroom Kahalu'u Reef Pool available

9.1 (38 Reviews) Holiday_home

The entire place is yours • 94 m² size • Outdoor swimming pool

Best Price Match

a living room with a blue couch and a kitchen at Pool & Jacuzzis, Free Parking, WiFi, AC, Comfy Beds, BBQ, and Great View in Honolulu

From US $309

Pool & Jacuzzis, Free Parking, WiFi, AC, Comfy Beds, BBQ, and Great View Pool available

8.9 (41 Reviews) Apartment

Apartments • Free on-site parking • Outdoor swimming pool

Honolulu Honolulu Zoo

Best Price Match