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

Total holiday rentals
Explore 1,840 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at €96 per night before taxes and fees

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

Family-friendly holiday rentals
1,080 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
1,030 properties have a dedicated workspace

Wifi availability
1,830 of Wailea holiday 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!
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 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.
4.99 out of 5 average rating, 199 reviews
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!
4.99 out of 5 average rating, 233 reviews
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!
4.97 out of 5 average rating, 116 reviews
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.
4.96 out of 5 average rating, 149 reviews
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!
4.95 out of 5 average rating, 155 reviews
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.
4.96 out of 5 average rating, 143 reviews
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.
4.95 out of 5 average rating, 200 reviews
*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
4.99 out of 5 average rating, 154 reviews
Last Minute Deal! Wailea Condo Oceanfront Complex
Step into your own private tropical oasis in this fabulous Wailea condo! This adorable 792 square foot, ground floor unit is walking distance to one of the most incredible beaches on Maui with tantalizing turquoise blue waters of the Pacific! This lavish condo boasts an open and airy living space you will love with AC throughout. Relax on the remarkable lanais with a table with seating for four.
4.83 out of 5 average rating, 191 reviews
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.
4.96 out of 5 average rating, 202 reviews
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.)
4.98 out of 5 average rating, 208 reviews
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 : )
4.93 out of 5 average rating, 122 reviewsPopular amenities for Wailea rentals with a pool
House rentals with a pool

Stunning ocean view Villa, Heated pool, Wailea
4.96 out of 5 average rating, 469 reviews
Condo in Kihei 2 BR - 2 bath Condo
4.88 out of 5 average rating, 119 reviews
Go for an Ocean Swim From a Fun Beach Villa
4.92 out of 5 average rating, 153 reviews
3B2B w/HotTub FamilyComfort HawaiianaCharm Central
4.82 out of 5 average rating, 114 reviews
Oceanview Home with Private pool and hot tub
4.94 out of 5 average rating, 50 reviews
South Maui • Pool • Hot Tubs• Beach • Ocean View
5.0 out of 5 average rating, 10 reviews
Walk-Out Kamaole Beach II | Sunset Lanai | Quiet
4.67 out of 5 average rating, 12 reviews
Aloha Aku Bamboo Suite – Discover Beachfront Seren
4.98 out of 5 average rating, 45 reviewsApartment rentals with a pool

Spacious 3bd on Golf Course I Grand Champions 105
4.93 out of 5 average rating, 127 reviews
Mana Kai Palms Oceanfront Condo: Keawakapu Beach
4.97 out of 5 average rating, 106 reviews
Luxury Condo w/wide Ocean View (Palms at Wailea)!
4.88 out of 5 average rating, 133 reviews
StunningReno*Palms in Wailea Condo-Beach*Golf*Pool
4.93 out of 5 average rating, 214 reviews
Upscale and Elegant Vistas
4.95 out of 5 average rating, 131 reviews
Coastal Dream Oceanfront Condo!
4.98 out of 5 average rating, 126 reviews
Beachfront Oceanview Wailea Ekahi 16B Studio W/AC
4.99 out of 5 average rating, 135 reviews
Luxury Vacationing Modern Condo Sept Specials
4.96 out of 5 average rating, 183 reviewsOther holiday rentals with a pool

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
4.96 out of 5 average rating, 146 reviews
Wailea Ekolu 1204 - Modern, Ocean View, Split AC !
5.0 out of 5 average rating, 6 reviews
Aloha Moon - The Honeymoon Hideaway
4.94 out of 5 average rating, 67 reviews
Tropical Escape to Wailea with Stunning Oceanview
4.98 out of 5 average rating, 50 reviews
Elua 1310 Oceanfront -Family Managed-Remodeled9/25
5.0 out of 5 average rating, 24 reviews
Wailea Ocean View Escape
4.98 out of 5 average rating, 63 reviews
Stunning Wailea 2/2, AC, Upper Fl, walk to beach
4.94 out of 5 average rating, 67 reviews
Wailea Hidden Gem
4.94 out of 5 average rating, 86 reviewsWhen is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €330 | €352 | €315 | €276 | €251 | €254 | €244 | €234 | €227 | €240 | €274 | €326 |
| 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 |
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- Rentals with pools Maui County
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- Rentals with pools United States
- Maui
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