
Vacation rentals with a pool in Wailea
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wailea
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Not suitable for children or infants.

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
Mana Kai 608 is a remodeled oceanfront condo DIRECTLY ON Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, on the border of Wailea and Kihei! Our condo is designed with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5 star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best Property Manager in Maui, Tracy O'Reilly to take amazing care of you!

Spacious garden oasis near Maui's best beaches!
Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located next to Keawakapu Beach and minutes to Wailea. Our condo is perfectly suited for couples and small families wanting space with stylish comfort in a prime location. Relax on a luxurious king-sized bed, sectional sofa w/ a pull-out sleeper, and a pack and play for toddlers! Enjoy the essentials of modern connectivity, a fully stocked kitchen, with two full bathrooms. Soak in paradise on two lush garden patios!

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.

Modern Renovated Palms at Wailea Condo!
MODERN CONDO WITH ATTENTION TO DETAIL! Our bright, modern island condo awaits you! Breathe easy knowing that you have everything at your fingertips. Enjoy your morning coffee on the large lanai. Pack a beach bag and head to one of the best beaches just a 10 minute walk away. Explore the Shops at Wailea. You will feel right at home cooking in our fully equipped kitchen. Close out your day by watching the sunset from the pool area and then stargazing on the lanai. Then repeat!

Luxurious Wailea Ocean Vistas
Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful lushness while enjoying a charming well-designed hideaway. We have considered every detail to provide the most effortlessly luxurious stay possible. With beaches nearby and two pools onsite, this island paradise has everything and more.

Luxury Condo w/wide Ocean View (Palms at Wailea)!
There is no better location than Wailea to experience your Maui vacation! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. This condo is only a short walk to one of the best beaches (Keawakapu) on Maui and is also in close proximity to the Shops at Wailea. We spared no expenses in stocking this condo with everything you need to make your Maui experience memorable and luxurious.

A.R.A Retreats: Garden Oasis
Nicknamed “Garden Oasis” for its beautiful little garden walk out off the Lanai onto a beautiful field. While it also has a amazing view of the pacific ocean the beautiful private walkout really set the tone for a relaxing and private oasis. Wailea Ekolu Village is a three-minute drive or 18 minute walk to the beautiful golden sands of Wailea Beach. The Shops at Wailea, Monkeypod Kitchen and so much more just a short walk away!

Wailea Ekolu Village 2/2 with stunning ocean view!
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.

130K Hawaiian Reno on Wailea Blue Golf *Ocean View
BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.

Wailea Gem-Remodeled Ocean View
Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.

Maui Wailea Brand New Modern Spacious Condo
Beautifully designed, modern, and brand new vacation condo is situated on the Wailea Blue golf course and the Wailea tennis club. Walk to Shops at Wailea and 3 min drive to Keawakapu Beach. Brand new kitchen, spa like bathroom with walk in shower, in-unit laundry. Relax with friends and families at this peaceful place to stay. Book your vacation today : )
Popular amenities for Wailea rentals with a pool
House rentals with a pool

Kihei 533- A/C, Free Parking, and WiFi

Go for an Ocean Swim From a Fun Beach Villa

Stunning One Bd Partial ocean, AC, wifi,Pool C209

Oceanview Home with Private pool and hot tub

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Luxe 3BR Pualei Beach House Retreat

Stunning ocean view, heated pool at home by Wailea
Condo rentals with a pool

Oceanfront Makena Surf G202 - Professionally

Very Comfortable Kamaole Sands Condo Sleeps 4

Ocean View! Pool! Ho'okipa @ Wailea Ekolu Village!

Oceanview condo at Ulua Beach w/ lanai

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

21A Grand Champions 1 Bed - Ulua & Mokapu beaches

Grand Champions 169 Beautiful 3 BR on the Fairway!
Other vacation rentals with a pool

Beach Front Wailea, Full Ocean View A/C, ELUA102

Luxury Oceanview Wailea Retreat with Sunset Views

Gem near Keawakapu Beach - Privacy and Ocean Views

Wailea Ocean View Escape

Ekahi 22C Toes in the Sand in Under 2 Minutes

Wailea Elua: Huge Ocean Views, Pool, AC & Hot Tub

Steps to Ocean View Pool, Walk to Beach

Ocean View w/AC - Wailea Elua 306
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $529 CAD | $563 CAD | $503 CAD | $446 CAD | $397 CAD | $411 CAD | $390 CAD | $375 CAD | $363 CAD | $384 CAD | $439 CAD | $522 CAD |
| Avg. temp | 16 °C | 16 °C | 16 °C | 17 °C | 18 °C | 18 °C | 19 °C | 20 °C | 19 °C | 19 °C | 18 °C | 17 °C |
Quick stats about vacation rentals with a pool in Wailea

Total vacation rentals
Explore 1,870 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at $139 CAD per night before taxes and fees

Verified guest reviews
Over 49,560 verified reviews to help you choose

Family-friendly vacation rentals
1,050 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
1,050 properties have a dedicated workspace

Wifi availability
1,870 of Wailea vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Honolulu Vacation rentals
- Oahu Vacation rentals
- Kauai Vacation rentals
- Island of Hawai'i Vacation rentals
- Kailua-Kona Vacation rentals
- Kona Vacation rentals
- Waikīkī Beach Vacation rentals
- Kaanapali Vacation rentals
- Kihei Vacation rentals
- North Kona Vacation rentals
- Princeville Vacation rentals
- Hilo Vacation rentals
- Apartment rentals Wailea
- Beach condo rentals Wailea
- Hotel rooms Wailea
- Rentals with a washer and dryer Wailea
- Beachfront rentals Wailea
- Fitness-friendly rentals Wailea
- Rentals with a kayak Wailea
- Luxury rentals Wailea
- Rentals with beach access Wailea
- Rentals with a hot tub Wailea
- Serviced apartment rentals Wailea
- Family-friendly rentals Wailea
- Townhouse rentals Wailea
- House rentals Wailea
- Condo rentals Wailea
- Rentals with outdoor seating Wailea
- Pet-friendly rentals Wailea
- Rentals with an EV charger Wailea
- Waterfront rentals Wailea
- Rentals with a patio Wailea
- Rentals with a sauna Wailea
- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Wailea Beach
- Honolua Bay
- Polo Beach
- Kapalua Bay Beach
- Old Lahaina Luau
- Whalers Village
- Ka'anapali Golf Courses
- Black Rock Beach
- Big Beach
- Maui Vista Condominium
- Maui Ocean Center
- Black Sand Beach
- Kihei Kai Nani
- Hāmoa Beach
- Peahi
- Maui Arts & Cultural Center
- KOA Resort
- Haleakala National Park
- Kahana Beach
- PacWhale Eco-Adventures
- Things to do Wailea
- Art and culture Wailea
- Food and drink Wailea
- Nature and outdoors Wailea
- Sports activities Wailea
- Things to do Maui County
- Food and drink Maui County
- Art and culture Maui County
- Sports activities Maui County
- Nature and outdoors Maui County
- Things to do Hawaii
- Entertainment Hawaii
- Tours Hawaii
- Nature and outdoors Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Art and culture Hawaii
- Wellness Hawaii
- Food and drink Hawaii
- Things to do United States
- Food and drink United States
- Tours United States
- Entertainment United States
- Nature and outdoors United States
- Wellness United States
- Sightseeing United States
- Art and culture United States
- Sports activities United States







