Cottage
10.0(209 Reviews)
2 Bedrooms
4 Guests
Private Pool
Oceanfront
Hot Tub
Parking
AU $1,541/Night
7 Nights - AU $10,784
Wailea Cottage Rentals & Holiday Homes
Find the best cottages in Wailea - We found 4 exact matches
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Compare Cottage Rentals in Wailea
10.0
Cottage
10.0(157 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
Pool
AU $1,000/Night
7 Nights - AU $7,003
Cottage
10.0(43 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
Ocean View
Balcony/Terrace
AU $1,624/Night
7 Nights - AU $11,370
Cottage
2 Bedrooms
4 Guests
- Balcony/Terrace
Kitchen
Air Conditioner
Internet
AU $382/Night
7 Nights - AU $2,676
People Visiting Wailea Also Like
Condo
10.0(209 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $931/Night
7 Nights - AU $6,517
Resort
10.0(5 Reviews)
24 Guests
Private Beach- Oceanfront
- Hot Tub
Breakfast
AU $4,921/Night
7 Nights - AU $34,445
AU $1,658/Night
7 Nights - AU $11,604
House
10.0(186 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
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AU $1,012/Night
7 Nights - AU $7,085
House
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
View
AU $2,159/Night
7 Nights - AU $15,113
Condo
10.0(164 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $1,210/Night
7 Nights - AU $8,472
Condo
10.0(161 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $735/Night
7 Nights - AU $5,145
AU $890/Night
7 Nights - AU $6,231
Condo
10.0(155 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $489/Night
7 Nights - AU $3,425
AU $2,131/Night
7 Nights - AU $14,916
Condo
10.0(149 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $677/Night
7 Nights - AU $4,741
AU $889/Night
7 Nights - AU $6,225
Condo
10.0(140 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $921/Night
7 Nights - AU $6,445
Condo
10.0(139 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $1,496/Night
7 Nights - AU $10,472
Villa
10.0(135 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $650/Night
7 Nights - AU $4,550
Condo
10.0(133 Reviews)
1 Bedroom
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $576/Night
7 Nights - AU $4,029
Condo
10.0(127 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $709/Night
7 Nights - AU $4,965
Condo
10.0(126 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $2,696/Night
7 Nights - AU $18,874
Condo
10.0(120 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $1,594/Night
7 Nights - AU $11,158
Condo
10.0(115 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $932/Night
7 Nights - AU $6,522
Condo
10.0(114 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $613/Night
7 Nights - AU $4,292
Condo
10.0(112 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $502/Night
7 Nights - AU $3,513
Condo
10.0(108 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $1,421/Night
7 Nights - AU $9,944
About Wailea Cottage Rentals on BedroomVillas.com.au
Seeking incredible premium cottages to rent near Wailea? BedroomVillas features more than 4 cottages that are ideal for your next trip. Discover high-end cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Wailea have hot baths, are kid-friendly & family-friendly, and are near top local attractions, to give guests the best travel experience they could ever wish for. BedroomVillas’ cottage listings come in all shapes and sizes for large groups, friends, or couples in Wailea.
Are you planning to travel to a lakeside, beach, or mountain area? Then we've got the places for you. BedroomVilla’s cottage rentals and boutique resorts and rentals offer a great selection, giving you direct access to the owners of these cottage properties, and providing you the best opportunity to find a great price for a great stay.
BedroomVillas offers 4 luxury holiday cottages and places to stay in Wailea. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget. Relax with BedroomVillas.
Cottage Rentals: Explore Top Destinations
Frequently Asked Questions About Wailea Rental Cottages
What are the top rated Cottage Rentals in Wailea?
There are a lot of options 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 Cottage Rentals in Wailea:
- Romantic, Luxury, Sensual Retreat - Couples Only
- Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
- Owner Direct - 35% off in Oct & Nov! - Elua Village 701, Luxury 2BR, Ocean View
- NEW KITCHEN REMODEL! Amazing View!
- Very Best Deluxe Ocean View.Panoramic View.First Class!
- 125+ 5 STAR REVIEWS SAYS IT ALL! Upgraded thru/vaulted ceil/Golf & Ocean view!
- Private S. Maui home w/ocean views, pool, hot tub
- Wailea Ekahi 40A - Your South Maui Oasis
- Amazing view, Close to the beach, Wailea Ekahi Unit 20i
- Maui Luxury with Island Serenity - Wailea Beach Villas Penthouse K107
How much does it cost to rent a cottage in Wailea?
The average cost for a cottage rental in Wailea is $789 per night. BedroomVillas.com.au has a wide list of great cottages near Wailea that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Wailea that allow pets?
Yes, here are the top cottage rentals in Wailea that allow you to bring your pet:
- Hawaiian Cottage and Personal Paradise/BBKM 2013/0004
- Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
- Oceanfront, beautiful, private property you have all to yourselves.
- Cozy Cottage in Beautiful Wailea
- Romantic, Luxury, Sensual Retreat - Couples Only
- Ho'olei at Grand Wailea
- Luxurious Wailea Ocean Vistas
- Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
See all pet-friendly vacation rentals in Wailea on BedroomVillas.com.au
Do you have any rental cottages in Wailea that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Wailea to find one that works for you.
Are there quality cottages in Wailea that have indoor swimming pools?
As of 2026, the data from BedroomVillas.com.au shows that there are Over 4 private swimming pools or cottages with indoor pools in the Wailea area along with other great amenities.
Do any cottages in Wailea have hot tubs?
About 4 cottages in Wailea boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Wailea on BedroomVillas.com.au
Are there luxury cottages in Wailea?
Yes, there are luxury cottages in Wailea. Find more luxury, lakefront, winter, & last-minute cottage rentals near Wailea.
