
Vacation rentals with a pool in Wailea
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Wailea

Total vacation rentals
Explore 1,840 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at G$22,965 GYD per night before taxes and fees

Verified guest reviews
Over 50,970 verified reviews to help you choose

Family-friendly vacation rentals
1,070 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
1,020 properties have a dedicated workspace

Wi-Fi availability
1,830 of Wailea vacation rentals include wi-fi 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!
Top-rated rentals with a pool in Wailea
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Mana Kai Palms Oceanfront Condo: Keawakapu Beach
Welcome to Mana Kai Palms Our luxurious, newly renovated condominium is located on Keawakapu Beach, named Maui's best for its pristine sand, clear waters, and abundant marine life. The Mana Kai Resort offers a wide range of amenities and with only 100 units, provides a warm, family feel. We are conveniently located minutes from all South Maui has to offer. Hosted by Tracy O'Reilly, a Superhost and #1 rated rental agent on Maui. Do as much as you want or as little as you desire at Mana Kai Palms

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury accommodations in the heart of Wailea, Maui. Our condo has lovely ocean views, views of the lush tropical gardens and the pool. Sunset views from the lanai are stunning. Gourmet kitchen. 2 HD TVs, Bose sound system, AC, washer/dryer in unit, complimentary assigned parking. 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 Our condo is 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, welcome to the beach! If you enjoy Wailea's 5 star resorts right down the beach, 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 PM in Maui, Tracy O'Reilly to take amazing care of you!

Large 1BR, Palms at Wailea, Pool, Walk to Beach
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!

Ekahi Ocean Studio: Wailea Paradise by the Beach
Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!
This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!

Oceanfront Mana Kai Penthouse..Heaven meets Earth!
Wake up to breathtaking, panoramic north-to-south ocean views from the Mana Kai’s top-floor penthouse level, just steps from Keawakapu Beach—2.75 miles of Wailea’s longest sandy shoreline at your door. Snorkel, swim, paddleboard, body surf, or watch whales from your private 200 sq. ft. lanai. This spacious 2-bedroom, 2-bath oceanfront suite sleeps four, with two king beds and a beautifully updated private bathroom for each bedroom.

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.

*Fully Remodeled* Modern Island Style*
I am looking forward to hosting you at the Palms at Wailea 606 and making your vacation fun and enjoyable. The Palms is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all within a few minutes. I offer you a clean, comfortable and memorable stay on the island. I want to make your Maui dreams come true! Mahalo and looking forward to seeing you! -Aini

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.

Ocean/Golf Course Views, Tropical Resort in Wailea
Breathe in and exhale slowly while gazing at the beautiful ocean, serene greenery and misty mountaintops. Make the most of a country-club setting by lounging on sun decks and swimming in heated pools. Retreat to an updated condo to unwind and fall asleep in a comfy bed. (This unit is suitable for a maximum of four (4) guests. Infants of any age are counted as guests.)

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views
Experience the best of Wailea from this rare 3BR/2BA luxury villa, featuring breathtaking views of the Pacific Ocean, Wailea Blue Golf Course and majestic Haleakalā. Spacious enough for families or groups, this exceptional retreat offers all the comforts of home—just a short walk from world-famous beaches, luxury resorts, fine dining and premier shopping.
Popular amenities for Wailea rentals with a pool
House rentals with a pool

Stunning ocean view Villa, Heated pool, Wailea

Condo in Kihei 2 BR - 2 bath Condo

Go for an Ocean Swim From a Fun Beach Villa

Oceanview Home with Private pool and hot tub

South Maui • Pool • Hot Tubs• Beach • Ocean View

Aloha Aku Bamboo Suite – Discover Beachfront Seren

Oceanfront Stunner w/ Cruiser Bikes & Pickleball

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet
Condo rentals with a pool

Luxury Vacationing Modern Condo Sept Specials

Last Minute Deal! Wailea Condo Oceanfront Complex

Coastal Dream Oceanfront Condo!

Very Comfortable Kamaole Sands Condo Sleeps 4

StunningReno*Palms in Wailea Condo-Beach*Golf*Pool

Spacious 3bd on Golf Course I Grand Champions 105

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Luxury condo • 180° Ocean Views • Steps to Beach
Other vacation rentals with a pool

Luxurious Wailea Ocean Vistas

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Go Golfing from a Peaceful Apartment in a Beach Community

Grand Champions 169 Beautiful 3 BR on the Fairway!

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

Tropical Escape to Wailea with Stunning Oceanview

Maui Kamaole in Kihei | Ocean View, Pool, Hot Tub

Wailea Ocean View Escape
Destinations to explore
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- Maui
- Kaanapali Beach
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- Maui Arts & Cultural Center
- Maui Ocean Center
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