
Holiday rentals near Windy Oaks Estate
We found 1,174 holiday rentals — enter your dates for availability
Take a look at holiday rentals within easy reach of Windy Oaks Estate that can be your home away from home. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a fireplace. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Windy Oaks Estate
Showing deals for:7 Nov - 14 Nov
Image gallery for Soquel Villa - 180 views of Monterey Bay w/ infinity pool, spa & movie theater

1010 out of 10 rating
Exceptional
(68 reviews)
Soquel Villa - 180 views of Monterey Bay w/ infinity pool, spa & movie theater
Soquel, CA
8% off
Price is £10,600
£10,600
£1,514 per night
includes taxes & fees
Image gallery for Gated Beach Front Retreat - Remodeled on 1.5 Acres Just Steps to the Beach

1010 out of 10 rating
Exceptional
(23 reviews)
Gated Beach Front Retreat - Remodeled on 1.5 Acres Just Steps to the Beach
Watsonville, CA
7% off
Price is £7,341
£7,341
£1,049 per night
includes taxes & fees
Image gallery for 2 Mi to Ocean: Pet-Friendly Abode in Aptos!

1010 out of 10 rating
Exceptional
(5 reviews)
2 Mi to Ocean: Pet-Friendly Abode in Aptos!
Aptos, CA
7% off
Price is £1,884
£1,884
£269 per night
includes taxes & fees
Image gallery for Peaceful Place to Relax

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Peaceful Place to Relax
San Martin, CA
8% off
Price is £2,968
£2,968
£424 per night
includes taxes & fees
Image gallery for Charming single-story home steps from the beach.

9.89.8 out of 10 rating
Exceptional
(32 reviews)
Charming single-story home steps from the beach.
Aptos, CA
11% off
Price is £2,223
£2,223
£318 per night
includes taxes & fees
Image gallery for 10 Steps to the Sand…Capitola Beach Front at the mouth of the Wharf-Pet Friendly

1010 out of 10 rating
Exceptional
(30 reviews)
10 Steps to the Sand…Capitola Beach Front at the mouth of the Wharf-Pet Friendly
Capitola, CA
8% off
Price is £3,618
£3,618
£517 per night
includes taxes & fees
Image gallery for Blue Diamond@Monterey Dunes OCEANFRONT 3bed/3bath-sleeps 7 Monterey/Santa Cruz

1010 out of 10 rating
Exceptional
(51 reviews)
Blue Diamond@Monterey Dunes OCEANFRONT 3bed/3bath-sleeps 7 Monterey/Santa Cruz
Castroville, CA
14% off
Price is £3,710
£3,710
£530 per night
includes taxes & fees
Image gallery for Pacific View Treehouse

1010 out of 10 rating
Exceptional
(13 reviews)
Pacific View Treehouse
Watsonville, CA
8% off
Price is £3,031
£3,031
£433 per night
includes taxes & fees
Image gallery for Sweeping ocean views! Perfect for families, steps to sand, ping pong, Pickleball

9.89.8 out of 10 rating
Exceptional
(110 reviews)
Sweeping ocean views! Perfect for families, steps to sand, ping pong, Pickleball
Watsonville, CA
8% off
Price is £5,725
£5,725
£818 per night
includes taxes & fees
Image gallery for Oceanfront Retreat at Pajaro Dunes. Beach Access, Hot Tub, BBQ, Pool Table.

9.29.2 out of 10 rating
Wonderful
(58 reviews)
Oceanfront Retreat at Pajaro Dunes. Beach Access, Hot Tub, BBQ, Pool Table.
Watsonville, CA
11% off
Price is £6,205
£6,205
£886 per night
includes taxes & fees
Image gallery for Cozy Creekside Cabin in Santa Cruz Mountains

1010 out of 10 rating
Exceptional
(30 reviews)
Cozy Creekside Cabin in Santa Cruz Mountains
Soquel, CA
8% off
Price is £1,033
£1,033
£148 per night
includes taxes & fees
Image gallery for Oceanfront Retreat Pajaro Dunes Beach, crashing wave views, private beach

1010 out of 10 rating
Exceptional
(14 reviews)
Oceanfront Retreat Pajaro Dunes Beach, crashing wave views, private beach
Watsonville, CA
8% off
Price is £7,444
£7,444
£1,063 per night
includes taxes & fees
Image gallery for Charming guest house in Aptos-3 min walk to beach!+EV Charger.

1010 out of 10 rating
Exceptional
(5 reviews)
Charming guest house in Aptos-3 min walk to beach!+EV Charger.
Aptos, CA
14% off
Price is £1,605
£1,605
£229 per night
includes taxes & fees
Image gallery for Pajaro Dunes Resort: Remodeled 3 Bedroom Beach Getaway

1010 out of 10 rating
Exceptional
(17 reviews)
Pajaro Dunes Resort: Remodeled 3 Bedroom Beach Getaway
Watsonville, CA
9% off
Price is £3,098
£3,098
£443 per night
includes taxes & fees
Image gallery for Casa de Ensueño with an Ocean View

1010 out of 10 rating
Exceptional
(93 reviews)
Casa de Ensueño with an Ocean View
Watsonville, CA
7% off
Price is £3,867
£3,867
£552 per night
includes taxes & fees
Image gallery for "2-bedroom Condo with Excellent Ocean View at Seascape Resort, Aptos"

1010 out of 10 rating
Exceptional
(133 reviews)
"2-bedroom Condo with Excellent Ocean View at Seascape Resort, Aptos"
Aptos, CA
18% off
Price is £2,343
£2,343
£335 per night
includes taxes & fees
Image gallery for Riverview Retreat Duplex-Captiola LOWER UNIT A

9.89.8 out of 10 rating
Exceptional
(7 reviews)
Riverview Retreat Duplex-Captiola LOWER UNIT A
Capitola, CA
7% off
Price is £3,004
£3,004
£429 per night
includes taxes & fees
Image gallery for Aptos Home w/ Decks & Hot Tub - 2 Mi to Beach!

9.49.4 out of 10 rating
Exceptional
(9 reviews)
Aptos Home w/ Decks & Hot Tub - 2 Mi to Beach!
Aptos, CA
7% off
Price is £2,418
£2,418
£345 per night
includes taxes & fees
Image gallery for Quaint Cabin in the Santa Cruz Mountains

1010 out of 10 rating
Exceptional
(15 reviews)
Quaint Cabin in the Santa Cruz Mountains
Soquel, CA
12% off
Price is £1,106
£1,106
£158 per night
includes taxes & fees
Image gallery for Welcome to Peace & Plenty! Newly remodeled 3 brm, house. 10 houses from sand!

1010 out of 10 rating
Exceptional
(93 reviews)
Welcome to Peace & Plenty! Newly remodeled 3 brm, house. 10 houses from sand!
Aptos, CA
7% off
Price is £3,002
£3,002
£429 per night
includes taxes & fees
Image gallery for Serene & Modern~ Ocean Front View~ 2 Bd 2 Bth~1st Fully Remodeled

1010 out of 10 rating
Exceptional
(81 reviews)
Serene & Modern~ Ocean Front View~ 2 Bd 2 Bth~1st Fully Remodeled
Watsonville, CA
7% off
Price is £2,396
£2,396
£342 per night
includes taxes & fees
Image gallery for New, Centrally Located guest house with Modern Amenities and Private Hot Tub

9.09.0 out of 10 rating
Wonderful
(12 reviews)
New, Centrally Located guest house with Modern Amenities and Private Hot Tub
Salinas, CA
8% off
Price is £1,079
£1,079
£154 per night
includes taxes & fees
Image gallery for Dog-OK at Capitola Vista #4

9.69.6 out of 10 rating
Exceptional
(35 reviews)
Dog-OK at Capitola Vista #4
Capitola, CA
7% off
Price is £1,989
£1,989
£284 per night
includes taxes & fees
Image gallery for Seascape Resort 2B Luxury Oceanview Villa, Steps From The Beach, 5 min to golf

9.49.4 out of 10 rating
Exceptional
(225 reviews)
Seascape Resort 2B Luxury Oceanview Villa, Steps From The Beach, 5 min to golf
Aptos, CA
11% off
Price is £2,255
£2,255
£322 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Villa
Chalet
Find the best place to stay - Windy Oaks Estate
Pacific View Treehouse
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Sunset Inn - Charming Beautiful Inn (Second Cabin)
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
127 reviews(127 reviews)
Superb 1-Bedroom Beach Condo at Seascape Beach Resort in Aptos, CA
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
GREAT OCEAN VIEWS, LAST MINUTE DEAL, SUMMER DATES AVAILABLE - BEAUTIFUL HOME!!
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
164 reviews(164 reviews)
Jaw-Dropping Beach-Front Retreat!
Sleeps 10 · 4 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
78 reviews(78 reviews)
Cozy, Ocean Front Condo NEW Pickleball Courts
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
307 reviews(307 reviews)
Top rated rentals - Windy Oaks Estate
Great time in Santa Cruz
1010 out of 10
Exceptionalexceptional
146 reviews(146 reviews)
Well equipped apartment. Very comfortable. Ideal location. Walkable to beach. No problem with car parking.
gordon i.
Stayed May 2025
Peace & Tranquility at the Beach
1010 out of 10
Exceptionalexceptional
129 reviews(129 reviews)
La Sirena provided just the answer to such a crazy world! Growing up in Santa Cruz was a blessing though I had moved away in 1990. Rarely visiting in the years since we had a large family gathering to attend & I wanted my family to experience the ocean way of life I grew up with, La Sirena provided it. The song of the waves does wonders for your heart & soul. Waking up for coffee & reading a book sitting in a chair watching the ocean never gets old. oh, & if you like mermaids this is your place! Nautical decor & old fashioned beach cottage charm, all within steps of the sand.
David M.
Stayed Jun 2024
Amazing stay at Santa Cruz
1010 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
We stayed for a week at Jim’s amazing house and it was everything we could have wished for and more! The house was beautiful and so clean and comfortable and gave us absolutely pure relaxation, The location is perfect too. The view of the lagoon is outstanding and you can even see the ocean! Jim was very responsive to any questions and so obliging to any requests and super helpful whilst giving us total privacy. We really cannot rate this place highly enough! We can’t wait to be back! Thanks for everything Jim!
Amanda F.
Stayed Oct 2023
Beach trip with grandkids
1010 out of 10
Exceptionalexceptional
216 reviews(216 reviews)
Great trip! House conveniently located for east beach access and access to all the Santa Cruz hot spots
Jami L.
Stayed Jul 2023
Outstanding!
1010 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
Jay was extremely helpful in showing us around the property, including the youtube videos for quick guide on the cinema room’s AV setup and house lighting. Insight into the local restaurants was also very helpful.
The house is only a 10 minute drive from town, yet very quiet and private. Everything in the house is top quality and spotless, providing a truly luxury experience. Both indoor and outdoor spaces are beautiful. Views from the house overlooking Monterey Bay are outstanding.
I highly recommend this place!
Norm R.
Stayed Dec 2019
Lovely place
1010 out of 10
Exceptionalexceptional
420 reviews(420 reviews)
This place is really amazing! the house is nice, clean and well equipped! You can immediately feel that the owners really love their house. You can find in there whatever you need or you have forgotten to take with you. Even if the best is outside the house: the beach, the birds, the seals, the sunset, the hummingbirds and even the opossum we spotted in the parking space!
The condo is quite secluded but it was good for us!
Perfect place if you are looking for a lot nature and relax.
anna p.
Stayed Aug 2018
- 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, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value