
Vacation rentals near Tedeschi Vineyards
We found 4,942 vacation rentals — enter your dates for availability
Choose the perfect vacation home within easy reach of Tedeschi Vineyards. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as WiFi and a hot tub. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Vacation rentals with weekly discounts - Tedeschi Vineyards
Showing deals for:Nov 7 - Nov 14
Image gallery for Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-Fi

9.69.6 out of 10 rating
Exceptional
(13 reviews)
Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-Fi
Kihei, HI
5% off
Price is CA $908
CA $908
CA $9,274 total
CA $9,274 total
includes taxes & fees
Image gallery for Exceptional Upcountry Villa with breathtaking views

1010 out of 10 rating
Exceptional
(44 reviews)
Exceptional Upcountry Villa with breathtaking views
Makawao, HI
10% off
Price is CA $836
CA $836
CA $7,918 total
CA $7,918 total
includes taxes & fees
Image gallery for Quiet Beachfront Large Family Estate... Great for multiple families . Sleeps 12

1010 out of 10 rating
Exceptional
(149 reviews)
Quiet Beachfront Large Family Estate... Great for multiple families . Sleeps 12
Kihei, HI
10% off
Price is CA $2,470
CA $2,470
CA $23,374 total
CA $23,374 total
includes taxes & fees
Image gallery for Luxurious Tropical Home with Heated Pool, 5min to Wailea Beach, Mini Split ACs!

1010 out of 10 rating
Exceptional
(64 reviews)
Luxurious Tropical Home with Heated Pool, 5min to Wailea Beach, Mini Split ACs!
Kihei, HI
5% off
Price is CA $2,026
CA $2,026
CA $18,735 total
CA $18,735 total
includes taxes & fees
Image gallery for Maalaea Kai 109 - OCEANFRONT Plus MOUNTAINVIEW SUNRISE. Clean & Bright

9.89.8 out of 10 rating
Exceptional
(57 reviews)
Maalaea Kai 109 - OCEANFRONT Plus MOUNTAINVIEW SUNRISE. Clean & Bright
Maalaea, FL
5% off
Price is CA $384
CA $384
CA $4,060 total
CA $4,060 total
includes taxes & fees
Image gallery for Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.

9.49.4 out of 10 rating
Exceptional
(89 reviews)
Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.
Makawao, HI
10% off
Price is CA $507
CA $507
CA $4,900 total
CA $4,900 total
includes taxes & fees
Image gallery for Best view in Maui. Condo fully remodeled. August special 10% weekly discount.

9.89.8 out of 10 rating
Exceptional
(49 reviews)
Best view in Maui. Condo fully remodeled. August special 10% weekly discount.
Maalaea, HI
9% off
Price is CA $626
CA $626
CA $6,102 total
CA $6,102 total
includes taxes & fees
Image gallery for Maalaea Banyans 411 - Modern Renovation, Direct Ocean Front, Incredible View, AC

9.49.4 out of 10 rating
Exceptional
(75 reviews)
Maalaea Banyans 411 - Modern Renovation, Direct Ocean Front, Incredible View, AC
Maalaea, HI
5% off
Price is CA $430
CA $430
CA $4,514 total
CA $4,514 total
includes taxes & fees
Image gallery for 50 steps to the Ocean! Newly remodeled!

9.29.2 out of 10 rating
Wonderful
(33 reviews)
50 steps to the Ocean! Newly remodeled!
Maalaea, HI
10% off
Price is CA $185
CA $185
CA $2,092 total
CA $2,092 total
includes taxes & fees
Image gallery for Ocean Front with Spectacular View

9.49.4 out of 10 rating
Exceptional
(63 reviews)
Ocean Front with Spectacular View
Maalaea, HI
10% off
Price is CA $276
CA $276
CA $2,470 total
CA $2,470 total
includes taxes & fees
Image gallery for SALE! Lauloa 410 - Top Floor, Direct Ocean Front, Stunning Renovation, Split AC

9.69.6 out of 10 rating
Exceptional
(85 reviews)
SALE! Lauloa 410 - Top Floor, Direct Ocean Front, Stunning Renovation, Split AC
Maalaea, HI
5% off
Price is CA $495
CA $495
CA $5,137 total
CA $5,137 total
includes taxes & fees
Image gallery for Newly Renovated Kihei Condo with Sunset Views – Steps From a Beautiful Beach!

9.89.8 out of 10 rating
Exceptional
(129 reviews)
Newly Renovated Kihei Condo with Sunset Views – Steps From a Beautiful Beach!
Kihei, HI
10% off
Price is CA $315
CA $315
CA $3,328 total
CA $3,328 total
includes taxes & fees
Image gallery for Breath taking ocean and volcano views! Pool,Close to beaches and everything else

9.89.8 out of 10 rating
Exceptional
(156 reviews)
Breath taking ocean and volcano views! Pool,Close to beaches and everything else
Kihei, HI
10% off
Price is CA $1,919
CA $1,919
CA $17,561 total
CA $17,561 total
includes taxes & fees
Image gallery for Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC

9.89.8 out of 10 rating
Exceptional
(54 reviews)
Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
Kihei, HI
5% off
Price is CA $522
CA $522
CA $5,419 total
CA $5,419 total
includes taxes & fees
Image gallery for OCEANFRONT Spectacular Condo - Breathtaking Ocean Views and 60ft From the Water!

1010 out of 10 rating
Exceptional
(109 reviews)
OCEANFRONT Spectacular Condo - Breathtaking Ocean Views and 60ft From the Water!
Maalaea, HI
5% off
Price is CA $294
CA $294
CA $2,936 total
CA $2,936 total
includes taxes & fees
Image gallery for Endless Waves, Incredible Direct Oceanfront Views!

9.89.8 out of 10 rating
Exceptional
(73 reviews)
Endless Waves, Incredible Direct Oceanfront Views!
Maalaea, HI
10% off
Price is CA $310
CA $310
CA $3,211 total
CA $3,211 total
includes taxes & fees
Image gallery for Palms At Wailea 1801, 2Bd 2Bath, FULL AC, Sleep 6, New Owner, Renovated,

9.89.8 out of 10 rating
Exceptional
(22 reviews)
Palms At Wailea 1801, 2Bd 2Bath, FULL AC, Sleep 6, New Owner, Renovated,
Kihei, HI
5% off
Price is CA $484
CA $484
CA $4,826 total
CA $4,826 total
includes taxes & fees
Image gallery for Studio apt. with A/C, Fridge, Semi-Private pool in the Center of kihei

9.49.4 out of 10 rating
Exceptional
(72 reviews)
Studio apt. with A/C, Fridge, Semi-Private pool in the Center of kihei
Kihei, HI
10% off
Price is CA $185
CA $185
CA $1,662 total
CA $1,662 total
includes taxes & fees
Image gallery for Maui Sunset Retreat: King Bed, Steps to the Beach, Pool, Gym, Sleeps 7!

9.69.6 out of 10 rating
Exceptional
(21 reviews)
Maui Sunset Retreat: King Bed, Steps to the Beach, Pool, Gym, Sleeps 7!
Kihei, HI
10% off
Price is CA $733
CA $733
CA $7,116 total
CA $7,116 total
includes taxes & fees
Image gallery for CLOUD 9 BEACH HOUSE, MAUI FAMILY OWNED, Walk to Beach, Oceanview, Clean

9.89.8 out of 10 rating
Exceptional
(79 reviews)
CLOUD 9 BEACH HOUSE, MAUI FAMILY OWNED, Walk to Beach, Oceanview, Clean
Kihei, HI
10% off
Price is CA $742
CA $742
CA $7,604 total
CA $7,604 total
includes taxes & fees
Image gallery for Cant get any closer to the OCEAN!

1010 out of 10 rating
Exceptional
(71 reviews)
Cant get any closer to the OCEAN!
Kihei, HI
10% off
Price is CA $1,176
CA $1,176
CA $11,014 total
CA $11,014 total
includes taxes & fees
Image gallery for Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor

1010 out of 10 rating
Exceptional
(82 reviews)
Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor
Kihei, HI
10% off
Price is CA $427
CA $427
CA $4,357 total
CA $4,357 total
includes taxes & fees
Image gallery for Highest Guest Rating at Mana Kai, Best Ocean Views, Luxury Amenities, Ocean End

1010 out of 10 rating
Exceptional
(201 reviews)
Highest Guest Rating at Mana Kai, Best Ocean Views, Luxury Amenities, Ocean End
Kihei, HI
10% off
Price is CA $949
CA $949
CA $8,958 total
CA $8,958 total
includes taxes & fees
Image gallery for Kanai a Nalu 314 - Modern, Renovated, Oceanfront Condo, Breathtaking Views, AC!

9.89.8 out of 10 rating
Exceptional
(30 reviews)
Kanai a Nalu 314 - Modern, Renovated, Oceanfront Condo, Breathtaking Views, AC!
Maalaea, HI
5% off
Price is CA $325
CA $325
CA $3,562 total
CA $3,562 total
includes taxes & fees
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Find the best place to stay - Tedeschi Vineyards
On the Beach! Popular Unit A6, Gorgeous Remodel. An Ideal Location.
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
184 reviews(184 reviews)
Kihei Maui Beach house - On the water
Sleeps 14 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
195-295/night, Oceanfront with 2 Master Suites, Fully Stocked, Amazing View!!!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
131 reviews(131 reviews)
2 Bedroom ocean front. 175. , 5 day stay special, 1 Month out.
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
142 reviews(142 reviews)
Kanai A Nalu-Spectacular Whale Watching, Beachfront, Wifi & Split Air thru out
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
94 reviews(94 reviews)
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
80 reviews(80 reviews)
Top rated rentals - Tedeschi Vineyards
Amazing view
1010 out of 10
Exceptionalexceptional
132 reviews(132 reviews)
Amazinh view from the balcony, we can see sea turtles from our balcony. Amazing sunset also.
Sebastien R.
Stayed Jul 2025
Perfect upcountry retreat
1010 out of 10
Exceptionalexceptional
227 reviews(227 reviews)
The property is a dream. Large house with separate entries for the walk out basement and upstairs units, perfect for two families to share. We loved the views, the fruit trees (particularly the lychees and mangoes) and my daughter was obsessed with the neighbour's goats who kept sneaking into our yard. The Eddie Tam park next door is huge and beautiful, great for sunset walks. We always stay in upcountry when we visit Maui, as we like the quiet and cooler temperatures, and central location on the island. The house had everything we needed - beach towels, sand toys, beach chairs and umbrella, small kitchen appliances, and a ton of washers and dryers so everyone could do laundry at the same time. The only negative was that the bathroom in the basement smelled awful. It was something we were able to tolerate but would reconsider staying in the basement if the problem isnt rectified. The owner was super responsive during our stay and also said she'd fix the bathroom issue. Overall we loved the place and we have wonderful memories from our visit. We look forward to returning.
Janice L.
Stayed Jul 2025
Paradise of Maui
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
We loved our stay! Liked how well stocked it was. We will be back again soon. Thank u!!
Charlene S.
Stayed May 2025
Stunning Views & Maui vibes.
1010 out of 10
Exceptionalexceptional
94 reviews(94 reviews)
When you walk into the listing you’re greeted with the same stunning ocean views as in the photos, very accurate. The decor fit the Hawaiian feel and the pool was an excellent size to swim and chill out. We had plenty of space. Host even let us have a late check out due to a late flight and that was so convenient. The only thing to mention is the response time on the host is on the slower side but she was so helpful. Would definitely stay here again and bring others.
Lexi S.
Stayed Apr 2025
Great stay
1010 out of 10
Exceptionalexceptional
194 reviews(194 reviews)
Amazing family vacation!
Emma H.
Stayed Mar 2025
A Great Stay
1010 out of 10
Exceptionalexceptional
220 reviews(220 reviews)
We had an excellent time at the B&B in upcountry Maui! The location was amazing, as we were so close to all the lovely farms and gardens. The guesthouse was immaculately maintained with great amenities, and Marsha was so friendly and hospitable. Highly recommend!
Dana C.
Stayed Feb 2025
Perfect stay
1010 out of 10
Exceptionalexceptional
184 reviews(184 reviews)
Ellen was so great, answering all my questions. Her suite was outfitted with almost everything we needed. Comfy bed. Perfect kitchen. The location is one patio back from the pool which was perfect - close enough with still providing privacy- front suites have people in front of them often. Seating around the pool and in the common BBQ area always available. Beach was perfect. Very quiet. Perfect for a nice and relaxing, quiet vacation.
I had read reviews about the beach being windy but we didn’t find that at all.
Absolutely loved our stay.
Maria B.
Stayed Nov 2024
Amazing!
1010 out of 10
Exceptionalexceptional
265 reviews(265 reviews)
This place is exactly what is advertised. My best friend and I booked for a girls get away and couldn't have been happier. The hosts are phenomenal with communication and the place is super clean. Highly recommened for a couple or 2 friends. Amazing location as well. Can walk to the beach and watch the sunrise/sunset, or any number of shops.
Trisha P.
Stayed Sep 2024
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value