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Wailea Vacation Homes and Villas with Pools

Find Luxury Places to Stay Near Wailea with a Swimming Pool. Find pool in Wailea, Hawaii.

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167 stays

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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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a bedroom with a bed and two tables with lamps at Maui Tranquility II in Kihei

From US $348

Maui Tranquility II Pool available

9.6 (30 Reviews) Apartment

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

Wailea Maui Meadows

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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

Wailea Maui Meadows

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a group of palm trees on the beach at sunset at Live da HI life--great beach and great views! in Wailea

From US $305

Live da HI life--great beach and great views! Pool available

9.0 (25 Reviews) Apartment

The entire place is yours • 76 m² size • Kitchen

Wailea Maui Meadows

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a dining room with a table and a view of the ocean at Kihei Alii Kai D207- Ocean view, walk to shops, dining, and Kam I Beach in Kihei

From US $295

Kihei Alii Kai D207- Ocean view, walk to shops, dining, and Kam I Beach Pool available

9.0 (16 Reviews) Apartment

The entire place is yours • 56 m² size • Kitchen

Wailea Maui Meadows

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a resort swimming pool with chairs and a building at Maui Vista 1210 in Kihei

From US $219

Maui Vista 1210 Pool available

8.1 (23 Reviews) Apartment

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

Wailea Maui Meadows

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a living room with a couch and a chair at 1BD Condo with Ocean Views: 40% OFF, Self Check-In in Kihei

From US $448

1BD Condo with Ocean Views: 40% OFF, Self Check-In Pool available

7.2 (31 Reviews) Apartment

The entire place is yours • 84 m² size • Free on-site parking

Wailea Maui Meadows

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a living room with a couch and a tv at Steps to Charley Young Beach, Ocean Views, Pool Retreat in Kihei

From US $278

Steps to Charley Young Beach, Ocean Views, Pool Retreat Pool available

7.4 (28 Reviews) Apartment

The entire place is yours • 81 m² size • Free on-site parking

Wailea Maui Meadows

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an overhead view of a pool with chairs and palm trees at Palms at Wailea in Wailea

From US $599

Palms at Wailea Pool available

7.9 (21 Reviews) Apartment

Apartments • Free on-site parking • Outdoor swimming pool

Wailea Maui Meadows

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a living room with a couch and a flat screen tv at 126 Hale Kamaole in Wailea

From US $280

126 Hale Kamaole Pool available

9.0 (11 Reviews) Apartment

The entire place is yours • 72 m² size • Swimming pool

Wailea Maui Meadows

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a dining table with chairs and a view of the ocean at Island Surf 306 · ISF 306 1BD w Ocean Views AC Pool Near Beach in Kihei

From US $636

Island Surf 306 · ISF 306 1BD w Ocean Views AC Pool Near Beach Pool available

9.4 (9 Reviews) Holiday_home

The entire place is yours • Kitchen • Sea view

Wailea Maui Meadows

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a living room with a white couch and a table at Pacific Shores A406 in Kihei

From US $695

Pacific Shores A406 Pool available

8.0 (11 Reviews) Apartment

The entire place is yours • 69 m² size • Outdoor swimming pool

Wailea Maui Meadows

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a table with two cups on a balcony with a view of the ocean at Kihei Surfside 306 · KSS 306 Updated BeachFront 1BD w Ocean View in Wailea

From US $772

Kihei Surfside 306 · KSS 306 Updated BeachFront 1BD w Ocean View Pool available

8.7 (8 Reviews) Holiday_home

The entire place is yours • Kitchen • Sea view

Wailea Maui Meadows

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a living room with a couch and a tv at Kihei Alii Kai A207 · KAK A207 Renovated Kihei Condo Near Beach in Kihei

From US $616

Kihei Alii Kai A207 · KAK A207 Renovated Kihei Condo Near Beach Pool available

8.4 (9 Reviews) Holiday_home

The entire place is yours • Kitchen • Swimming pool

Wailea Maui Meadows

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a living room with a couch and a table at Kihei Akahi C320- Kihei Studio, walk to shops, dining, & the beach in Wailea

From US $247

Kihei Akahi C320- Kihei Studio, walk to shops, dining, & the beach Pool available

7.9 (11 Reviews) Apartment

The entire place is yours • 37 m² size • Free on-site parking

Wailea Maui Meadows

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a table on a balcony with a view of the ocean at Kihei Akahi C302 · AKH C302 Spacious 2BD Condo w Ocean Breeze AC in Wailea

From US $713

Kihei Akahi C302 · AKH C302 Spacious 2BD Condo w Ocean Breeze AC Pool available

10.0 (4 Reviews) Holiday_home

The entire place is yours • Kitchen • Sea view

Wailea Maui Meadows

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a kitchen and dining room with a table and chairs at Upscale Wailea! 2-2 with Ocean View in Wailea

From US $620

Upscale Wailea! 2-2 with Ocean View Pool available

8.8 (7 Reviews) Holiday_home

The entire place is yours • 100 m² size • Free on-site parking

Wailea Maui Meadows

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a table and chairs on a balcony with a view at Wailea Ekahi 17D · WEK 17D Wailea Retreat w Ocean View Pool AC in Wailea

From US $776

Wailea Ekahi 17D · WEK 17D Wailea Retreat w Ocean View Pool AC Pool available

8.7 (7 Reviews) Holiday_home

The entire place is yours • On-site parking • Outdoor swimming pool

Wailea Maui Meadows

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a balcony with a table and a palm tree at Kihei Alii Kai C405 · KAK C405 Updated 2BD Condo Across Beach w in Kihei

From US $713

Kihei Alii Kai C405 · KAK C405 Updated 2BD Condo Across Beach w Pool available

8.4 (8 Reviews) Holiday_home

The entire place is yours • Kitchen • Sea view

Wailea Maui Meadows

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a living room with a couch and a table at 3BR Penthouse- ocean views, lanais, ACs, hot tub, pool, sauna, steps to beach in Kihei

From US $865

3BR Penthouse- ocean views, lanais, ACs, hot tub, pool, sauna, steps to beach Pool available

8.9 (6 Reviews) Apartment

The entire place is yours • 106 m² size • Free on-site parking

Wailea Maui Meadows

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About Wailea Vacation Rentals with Pools on NearbyHoliday

Looking for pool in Wailea? Compare top options in Hawaii.

Find Wailea Rentals, Hotels, and Resorts with Swimming Pools.

Discover 167 places to stay, including hotel waterparks, vacation homes, resorts, private villas, and condos in Wailea that feature indoor, outdoor, or private pools.

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Frequently Asked Questions About Vacation Rentals With Pools in Wailea

There are a lot of vacation rentals with pools in Wailea. If you plan on staying in the Wailea area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals with Pools in Wailea:

We have many family-friendly luxury rentals in Wailea. The top family-friendly holiday rentals in Wailea are:

See all family-friendly luxury rentals in Wailea on NearbyHoliday

Many vacation rentals with pools on NearbyHoliday have a heated pool. These are some popular rentals in Wailea that you may consider:

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