South Maui Condos Permitted for Short-Term Rental

South Maui comprises the towns of Kihei, Maalaea, Makena, and Wailea. Being on the leeward side of Mount Haleakala, it is drier and sunnier than the rest of Maui. With the predictable perfect climate, visitors can fully enjoy the spectacular beauty of the mile-long white sandy crescent-shaped shores, explore the lava fields, and participate in the many water activities available in the area.  

South Maui is one of the top two most popular tourist destinations on the island region of Maui. Instead of hotel-style resorts, the area has a great selection of vacation Condo rentals that guests who prefer a more private relaxation would surely love.

Being locals of Maui, the Maui Property Team has extensive knowledge and understanding of which condo units in the area are included in the permitted short-term rental classification. Contact us today! You may also visit our website to search for the best rental condo. Our website is so easy to use, and you can also save searches and get daily email alerts as new listings become available.

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View All Latest South Maui Condos Permitted for Short Term Rental

2737 S Kihei Rd Unit 2-337, Kihei image
2737 S Kihei Rd Unit 2-337, Kihei — Hale Kamaole $1,075,000

Have you been wanting that perfect piece of Paradise? Here it is a two bedroom two bath with a loft, that can be used like a third bedroom. Top floor unit with marvelo...

  • 2 Beds
  • 2 Baths
  • 398433 MLS
  • Hale Kamaole Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Kumulani Vacations&Realty Inc

Listing courtesy of Kumulani Vacations&Realty Inc.

2495 S Kihei Rd Unit 4-121, Kihei image
2495 S Kihei Rd Unit 4-121, Kihei — Kihei Kai Nani $789,000

Picture perfect unit with new Kitchen and Bath along with new furniture, and a Murphy bed makes this a dream unit to own. Never been rented but very easy to do if new buy...

  • 1 Beds
  • 1 Baths
  • 398432 MLS
  • Kihei Kai Nani Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop-Ku

Listing courtesy of Coldwell Banker Island Prop-Ku.

2385 S Kihei Rd Unit 507, Kihei image
2385 S Kihei Rd Unit 507, Kihei — Kamaole Beach Royale $888,000

FABULOUS *OCEAN VIEW* 5th Floor KAMAOLE BEACH ROYALE. Located across from Kamaole 1 Beach Park this UPDATED Condo features: CONTEMPORARY FURNITURE, MODERN LIGHTING, MURPH...

  • 1 Beds
  • 1 Baths
  • 398430 MLS
  • Kamaole Beach Royale Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

679 S Kihei Rd Unit D104, Kihei image
679 S Kihei Rd Unit D104, Kihei — Kihei Bay Vista $695,000

This cozy and well-equipped 1 bedroom, 1 bath unit is located in the desirable "D" building at Kihei Bay Vista, and it backs up to a green space. This condo has three ste...

  • 1 Beds
  • 1 Baths
  • 398424 MLS
  • Kihei Bay Vista Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Sunny Maui Vacations

Listing courtesy of Sunny Maui Vacations.

3800 WAILEA ALANUI Dr Unit G201, Kihei image
3800 WAILEA ALANUI Dr Unit G201, Kihei — Wailea Beach Villas $10,995,000

Wailea's Finest Ocean Front Development Wailea Beach Villas! Rare opportunity to own a Fully Furnished 3 Bedroom and 3.5 Bath Villa with dramatic Ocean Views! The elegant...

  • 3 Beds
  • 3.5 Baths
  • 398409 MLS
  • Wailea Beach Villas Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop-KP

Listing courtesy of Coldwell Banker Island Prop-KP.

3600 WAILEA ALANUI Dr Unit 406, Kihei image
3600 WAILEA ALANUI Dr Unit 406, Kihei — Wailea Elua I B $3,550,000

Welcome to Wailea Elua Village, an exclusive luxury beachfront condominium complex located in the heart of Wailea, South Maui. Nestled in front of Maui’s most prestigiou...

  • 2 Beds
  • 2 Baths
  • 398398 MLS
  • Wailea Elua I B Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Maui International R E Srvs

Listing courtesy of Maui International R E Srvs.

760 S Kihei Rd Unit 427, Kihei image
760 S Kihei Rd Unit 427, Kihei — Menehune Shores $1,395,000

Elegantly appointed remodeled 2 bedroom / 2 bath unit located on the 4th floor with awesome ocean views. Stunning end-unit with integrated air conditioning with nearly 90...

  • 2 Beds
  • 2 Baths
  • 398347 MLS
  • Menehune Shores Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Compass

Listing courtesy of Compass.

3600 WAILEA ALANUI Dr Unit 907, Kihei image
3600 WAILEA ALANUI Dr Unit 907, Kihei — Wailea Elua I A $3,700,000

Serenity that is seconds away from the sand at Ulua Beach. Enjoy a wonderful 2 Bedroom + 2 Full Bathroom, first floor vacation home that been lovingly upgraded and cared ...

  • 2 Beds
  • 2 Baths
  • 398333 MLS
  • Wailea Elua I A Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Wailea Vacation Rentals

Listing courtesy of Wailea Vacation Rentals.

2191 S Kihei Rd Unit 1110, Kihei image
2191 S Kihei Rd Unit 1110, Kihei — Maui Vista $850,000

All the right things were done and done well in this gorgeous ground floor unit in the front building at Maui Vista including tile flooring throughout the main living are...

  • 1 Beds
  • 1 Baths
  • 398315 MLS
  • Maui Vista Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

Listing courtesy of Hawaii Life (W).

4850 MAKENA ALANUI Rd Unit C106, Kihei image
4850 MAKENA ALANUI Rd Unit C106, Kihei — Makena Surf $4,985,000

Enjoy breathtaking unobstructed ocean, outer island, and sunset views from this extra-large, elegantly renovated, two-bedroom, two-bath Makena Surf condo! This 1,600 squ...

  • 2 Beds
  • 2 Baths
  • 398293 MLS
  • Makena Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

Listing courtesy of Hawaii Life (W).

155 WAILEA IKE Pl Unit 52, Kihei image
155 WAILEA IKE Pl Unit 52, Kihei — Grand Champions $1,775,000

Grand Champions 52 has ocean views from the lanai and the master bedroom, plus, direct views of Maui’s dreamy winter-months sunsets — A Wailea vacation condo at it’s fine...

  • 2 Beds
  • 2 Baths
  • 398265 MLS
  • Grand Champions Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

2495 S Kihei Rd Unit 254, Kihei image
2495 S Kihei Rd Unit 254, Kihei — Kihei Kai Nani $745,000

Paradise awaits. Situated in one of Kihei's most desired areas, lies Kihei Kai Nani 254, a modern short term rentable unit, boasting an unrivaled central location, desira...

  • 1 Beds
  • 1 Baths
  • 398259 MLS
  • Kihei Kai Nani Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

61 N Kihei Rd Unit 4, Kihei image
61 N Kihei Rd Unit 4, Kihei — Kihei Kai $695,000

North Kihei hidden gem. Kihei Kai unit #4 is a turnkey vacation rental in a small 24 unit Beachfront complex on Sugar Beach. Unit 4 has a partial ocean view from the larg...

  • 1 Beds
  • 1 Baths
  • 398251 MLS
  • Kihei Kai Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of AA Oceanfront Rentals & Sales

Listing courtesy of AA Oceanfront Rentals & Sales.

4850 MAKENA ALANUI Rd Unit G303, Kihei image
4850 MAKENA ALANUI Rd Unit G303, Kihei — Makena Surf $4,000,000

This RARE and stunning location directly on the ocean has breathtaking views of the Makena coastline, Molokini and Kahoolawe. Beautiful natural light fills the living are...

  • 2 Beds
  • 2 Baths
  • 398224 MLS
  • Makena Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Equity One Real Estate Inc (P)

Listing courtesy of Equity One Real Estate Inc (P).

2777 S Kihei Rd Unit M109, Kihei image
2777 S Kihei Rd Unit M109, Kihei — Maui Kamaole $1,099,000

Are you looking for an immaculate vacation rental in one of the best locations on Maui? You found it! Maui Kamaole M109 is at the top of the complex; and this is the newe...

  • 1 Beds
  • 2 Baths
  • 398212 MLS
  • Maui Kamaole Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

3800 WAILEA ALANUI Blvd Unit B101, Kihei image
3800 WAILEA ALANUI Blvd Unit B101, Kihei — Wailea Beach Villas $14,990,000

THE BEACHFRONT VILLA offers you a phenomenal opportunity to own "the one and only" Direct Ocean Front Villa currently on the market with unobstructed ocean views @ Wailea...

  • 3 Beds
  • 3.5 Baths
  • 398180 MLS
  • Wailea Beach Villas Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Compass

Listing courtesy of Compass.

3600 Wailea Alanui Dr Unit 1201, Kihei image
3600 Wailea Alanui Dr Unit 1201, Kihei — Wailea Elua I A $2,895,000

Live, seaside. Prominently situated in one of Wailea’s most highly-desired resort style complexes, this timeless, ground-floor residence boasts awe-inspiring ocean views,...

  • 1 Beds
  • 1 Baths
  • 398179 MLS
  • Wailea Elua I A Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

1002 S Kihei Rd Unit 305, Kihei image
1002 S Kihei Rd Unit 305, Kihei — Waipuilani $575,000 ▼

An Island Oasis found in Kihei at Waipuilani. This one-bedroom, furnished condo sits on the third floor, allowing the ocean breeze to flow freely through the floor-to-cei...

  • 1 Beds
  • 1 Baths
  • 398017 MLS
  • Waipuilani Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Maui Property LLC

Listing courtesy of Maui Property LLC.

10 Wailea Ekolu Pl Unit 207, Kihei image
10 Wailea Ekolu Pl Unit 207, Kihei — Wailea Ekolu $1,795,000

This stunning ground floor unit at Wailea Ekolu offers breathtaking ocean views of Molokini, Kaho'olawe, and Lana'i, and is rarely available for purchase. Recently renova...

  • 1 Beds
  • 2 Baths
  • 397984 MLS
  • Wailea Ekolu Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

155 WAILEA IKE Pl Unit 51, Kihei image
155 WAILEA IKE Pl Unit 51, Kihei — Grand Champions $1,575,000

Grand Champions #51 is a 1056 s.f., 2 bd/2 ba, ground floor end-unit without a single stair step from its dedicated parking spot to the front door! You approach along a l...

  • 2 Beds
  • 2 Baths
  • 398081 MLS
  • Grand Champions Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Maui Real Estate Advisors LLC

Listing courtesy of Maui Real Estate Advisors LLC.

145 N Kihei Rd Unit 328, Kihei image
145 N Kihei Rd Unit 328, Kihei — Sugar Beach Resort $1,295,000

Another Fantastic "Remodeled" BEACHFRONT condo located at Sugar Beach Resort. Remodel includes: Green Granite Countertops, Beach Style tile floors, Bathroom renovation in...

  • 1 Beds
  • 1 Baths
  • 398100 MLS
  • Sugar Beach Resort Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

155 WAILEA IKE Pl Unit 30, Kihei image
155 WAILEA IKE Pl Unit 30, Kihei — Grand Champions $1,670,000

Quintessential Golf course location! A private corner villa overlooking the Wailea Blue course, with breathtaking views of Haleakala. This idyllic setting offers a relaxe...

  • 2 Beds
  • 2 Baths
  • 397941 MLS
  • Grand Champions Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Island Sotheby's Int'l Rlty(L)

Listing courtesy of Island Sotheby's Int'l Rlty(L).

1993 S Kihei Rd Unit 402, Kihei image
1993 S Kihei Rd Unit 402, Kihei — Island Surf $700,000

Awesome 180 degree ocean and coastline views with a direct facing position in the Island Surf condominium. This is a very centralized property that visitors and resident...

  • 1 Beds
  • 1 Baths
  • 397898 MLS
  • Island Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop-KP

Listing courtesy of Coldwell Banker Island Prop-KP.

2777 S Kihei Rd Unit K108, Kihei image
2777 S Kihei Rd Unit K108, Kihei — Maui Kamaole $1,250,000

There are only 14 of these rare, ground floor, den units in the complex. Situated in the center of the complex close to the tropical pool. This 1 bedroom + den, 2 bathroo...

  • 1 Beds
  • 2 Baths
  • 397842 MLS
  • Maui Kamaole Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

2142 Iliili Rd Unit 203, Kihei image
2142 Iliili Rd Unit 203, Kihei — Punahoa Beach Apts $1,250,000

Punahoa Beach Apartment #203 is the one you’ve been waiting for! Maui Oceanfront Bliss at its finest! You simply cannot get any closer to the ocean. Punahoa Beach is idea...

  • 1 Beds
  • 1 Baths
  • 397836 MLS
  • Punahoa Beach Apts Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

3300 Wailea Alanui Dr Unit 37D, Kihei image
3300 Wailea Alanui Dr Unit 37D, Kihei — Wailea Ekahi I $1,750,000 ▼

Situated in the highly desirable ocean-front complex of Wailea Ekahi, this beautifully renovated unit offers spacious indoor and outdoor luxury living with an ocean view ...

  • 1 Beds
  • 2 Baths
  • 397734 MLS
  • Wailea Ekahi I Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(Ka)

Listing courtesy of Coldwell Banker Island Prop(Ka).

1993 S Kihei Rd Unit 504, Kihei image
1993 S Kihei Rd Unit 504, Kihei — Island Surf $695,000

Island Surf 504 allows short term rentals and features excellent ocean views. Enjoy watching surfers and daily Sunset views from your lanai. The Cove surf-break directly...

  • 1 Beds
  • 1 Baths
  • 397720 MLS
  • Island Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Berkshire Hathaway Maui Prop-W

Listing courtesy of Berkshire Hathaway Maui Prop-W.

3550 Wailea Alanui Dr Unit E4, Kihei image
3550 Wailea Alanui Dr Unit E4, Kihei — Andaz Residences $12,950,000

Andaz Residences E4 offers a rare and unique opportunity for luxurious modern living in your ocean view, 3 bedroom, 4 bath private penthouse with full access to all Andaz...

  • 3 Beds
  • 4 Baths
  • 397631 MLS
  • Andaz Residences Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Royal Realty LLC

Listing courtesy of Royal Realty LLC.

2695 S Kihei Rd Unit Bldg 6#207, Kihei image
2695 S Kihei Rd Unit Bldg 6#207, Kihei — Kamaole Sands $998,000

This is a beautifully remodeled, inner-courtyard unit, with the larger lanai and money-saving split system air conditioning units. In the open-plan kitchen you'll find qu...

  • 1 Beds
  • 2 Baths
  • 397367 MLS
  • Kamaole Sands Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of FlatList.com

Listing courtesy of FlatList.com.

2495 S Kihei Rd Unit 211, Kihei image
2495 S Kihei Rd Unit 211, Kihei — Kihei Kai Nani $759,000 ▼

The heart of South Kihei - Kihei Kai Nani! Located across to one of the best beaches on the island, Kamaole Beach II. This beautiful 1 bed 1 bath, 621 sf. vacation renta...

  • 1 Beds
  • 1 Baths
  • 397291 MLS
  • Kihei Kai Nani Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

3800 WAILEA ALANUI Blvd Unit K-208, Kihei image
3800 WAILEA ALANUI Blvd Unit K-208, Kihei — Wailea Beach Villas $8,495,000

Wailea Beach Villas is revered as one of Maui's Top Destination Resorts. Approx. 75% of WBV units are highly desired legal vacation rentals. Located on Wailea Beach, adja...

  • 3 Beds
  • 3 Baths
  • 397279 MLS
  • Wailea Beach Villas Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Maui Real Estate Advisors LLC

Listing courtesy of Maui Real Estate Advisors LLC.

145 N Kihei Rd Unit 433, Kihei image
145 N Kihei Rd Unit 433, Kihei — Sugar Beach Resort $1,280,000 ▼

Another Fantastic "Remodeled" BEACHFRONT condo located at Sugar Beach Resort. Remodel in Sept. 2022 includes: New bathroom sink, faucet, quartz countertops and backsplash...

  • 1 Beds
  • 1 Baths
  • 397251 MLS
  • Sugar Beach Resort Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

4000 Wailea Alanui Dr Unit 102, Kihei image
4000 Wailea Alanui Dr Unit 102, Kihei — Wailea Point I Ii Iii $17,500,000 ▼

Simply the finest residence in Hawaii’s finest condominium development … There is nothing else like Wailea Point residence 102, and never can be. The LOCATION is 75 fee...

  • 3 Beds
  • 3 Baths
  • 397095 MLS
  • Wailea Point I Ii Iii Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Wailea Point Realty, Inc.

Listing courtesy of Wailea Point Realty, Inc..

3800 WAILEA ALANUI Blvd Unit 204, Kihei image
3800 WAILEA ALANUI Blvd Unit 204, Kihei — Wailea Beach Villas $5,850,000 ▼

Wailea Beach Villas 204 is one of the most advantageous units of this luxurious complex and is located in the penthouse building. Current owners have done a remarkable re...

  • 2 Beds
  • 2 Baths
  • 396969 MLS
  • Wailea Beach Villas Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

3800 WAILEA ALANUI Blvd Unit 312, Kihei image
3800 WAILEA ALANUI Blvd Unit 312, Kihei — Wailea Beach Villas $6,900,000 ▼

Blissfully Elevated Wailea Living…Prominently positioned in one of the most prestigious oceanfront luxury resorts in Hawaii, Wailea Beach Villas, lies Unit 312. Situated ...

  • 3 Beds
  • 3 Baths
  • 396774 MLS
  • Wailea Beach Villas Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

12 S Kihei Rd Unit C10, Kihei image
12 S Kihei Rd Unit C10, Kihei — Maalaea Surf $2,100,000

Rare Beachfront condo on beautiful sugar beach. Maalaea Surf condos is a gorgeous beachfront property located in North Kihei with amenities that include an oceanfront po...

  • 2 Beds
  • 2 Baths
  • 396760 MLS
  • Maalaea Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop-Ku

Listing courtesy of Coldwell Banker Island Prop-Ku.

63 Hoolei Cir Unit B2, Kihei image
63 Hoolei Cir Unit B2, Kihei — Hoolei $6,250,000

Location, location, location! Epic ocean views and one of the finest villas in the community make Ho'olei 63-2 an exclusive and highly desired opportunity. The Maile floo...

  • 3 Beds
  • 3.5 Baths
  • 396726 MLS
  • Hoolei Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

3800 WAILEA ALANUI Blvd Unit G301, Kihei image
3800 WAILEA ALANUI Blvd Unit G301, Kihei — Wailea Beach Villas $12,750,000

THE LUXURY VILLA @ Wailea Beach Villas is STUNNING! This is your opportunity to own this very prestigious and private TOP floor fully furnished single level contemporary ...

  • 3 Beds
  • 3.5 Baths
  • 396334 MLS
  • Wailea Beach Villas Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Compass

Listing courtesy of Compass.

10 WAILEA EKOLU Pl Unit 1507, Kihei image
10 WAILEA EKOLU Pl Unit 1507, Kihei — Wailea Ekolu $2,695,000

Experience a seamless blend of tropical, island living at Wailea Ekolu 1507. Accentuating the best of Wailea living, this timeless 2 bed, 2 bath unit boasts jaw-dropping ...

  • 2 Beds
  • 2 Baths
  • 395492 MLS
  • Wailea Ekolu Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

1032 S Kihei Rd Unit A507, Kihei image
1032 S Kihei Rd Unit A507, Kihei — Maui Sunset $900,000 ▲

Maui Sunset is a great oceanside complex in South Maui for owners and guests! The grounds are beautiful, well cared for and there is lots of room for All. The large pool ...

  • 1 Beds
  • 2 Baths
  • 395116 MLS
  • Maui Sunset Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Moffett Properties LLC

Listing courtesy of Moffett Properties LLC.

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