Vacation rentals near Sky Sailing
We found 260 vacation rentals — enter your dates for availability
Find the perfect vacation home that's near Sky Sailing. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as a garden and pool. At the end of the day, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.
Vacation rentals with weekly discounts - Sky Sailing
Showing deals for:Oct 17 - Oct 24
Image gallery for Julian Cafe Family Cottage - Includes Breakfast at The Julian Cafe & Bakery
1010 out of 10 rating
Exceptional
(8 reviews)
Julian Cafe Family Cottage - Includes Breakfast at The Julian Cafe & Bakery
Julian, CA
9% off
Price is $341
$341
$2,388 for 7 nights
$2,388 for 7 nights
Includes all fees
Image gallery for Moonlit Retreat 6 Bedroom Borrego Pool/HotTub Home
1010 out of 10 rating
Exceptional
(9 reviews)
Moonlit Retreat 6 Bedroom Borrego Pool/HotTub Home
Borrego Springs, California
12% off
Price is $651
$651
$4,558 for 7 nights
$4,558 for 7 nights
Includes all fees
Image gallery for Amazing desert oasis
1010 out of 10 rating
Exceptional
(13 reviews)
Amazing desert oasis
Borrego Springs, CA
30% off
Price is $290
$290
$2,033 for 7 nights
$2,033 for 7 nights
Includes all fees
Image gallery for Starlit Ranch| Pool and Spa Estate| Sunrise and Sunset Views
8.68.6 out of 10 rating
Excellent
(12 reviews)
Starlit Ranch| Pool and Spa Estate| Sunrise and Sunset Views
Borrego Springs, California
8% off
Price is $1,082
$1,082
$7,575 for 7 nights
$7,575 for 7 nights
Includes all fees
Image gallery for La Paz - Adobe desert home on 6 acres, hot tub, cowboy pool, hiking
1010 out of 10 rating
Exceptional
(21 reviews)
La Paz - Adobe desert home on 6 acres, hot tub, cowboy pool, hiking
Borrego Springs, CA
18% off
Price is $266
$266
$1,861 for 7 nights
$1,861 for 7 nights
Includes all fees
Image gallery for Cozy Desert Hideout with Pool
9.49.4 out of 10 rating
Exceptional
(18 reviews)
Cozy Desert Hideout with Pool
Borrego Springs, CA
13% off
Price is $228
$228
$1,595 for 7 nights
$1,595 for 7 nights
Includes all fees
Image gallery for Desert Oasis with Pool, Fire Pit, Game Room, and Dry Bar
1010 out of 10 rating
Exceptional
(44 reviews)
Desert Oasis with Pool, Fire Pit, Game Room, and Dry Bar
Borrego Springs, CA
9% off
Price is $516
$516
$3,610 for 7 nights
$3,610 for 7 nights
Includes all fees
Image gallery for Perfect Mountain Home! 3 BR, spacious & clean with ping pong, foosball & games!
1010 out of 10 rating
Exceptional
(58 reviews)
Perfect Mountain Home! 3 BR, spacious & clean with ping pong, foosball & games!
Julian, CA
13% off
Price is $297
$297
$2,076 for 7 nights
$2,076 for 7 nights
Includes all fees
Image gallery for Wine Country Cabin Near San Diego - on private 9 acres
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Wine Country Cabin Near San Diego - on private 9 acres
Ramona, CA
18% off
Price is $148
$148
$1,034 for 7 nights
$1,034 for 7 nights
Includes all fees
Image gallery for Julian Cafe Couples Cottage - Breakfast Included at The Julian Cafe & Bakery!
1010 out of 10 rating
Exceptional
(10 reviews)
Julian Cafe Couples Cottage - Breakfast Included at The Julian Cafe & Bakery!
Julian, CA
9% off
Price is $195
$195
$1,363 for 7 nights
$1,363 for 7 nights
Includes all fees
Image gallery for Cristine's Cozy Cottage in the Woods - Close to Town and Pet Friendly!
1010 out of 10 rating
Exceptional
(50 reviews)
Cristine's Cozy Cottage in the Woods - Close to Town and Pet Friendly!
Julian, CA
8% off
Price is $161
$161
$1,129 for 7 nights
$1,129 for 7 nights
Includes all fees
Image gallery for Pitch Perfect Mid-Century 2 Bedroom, 2 Bathroom ~ Amazing Hiking, Star Gazing ~
1010 out of 10 rating
Exceptional
(109 reviews)
Pitch Perfect Mid-Century 2 Bedroom, 2 Bathroom ~ Amazing Hiking, Star Gazing ~
Borrego Springs, CA
12% off
Price is $222
$222
$1,553 for 7 nights
$1,553 for 7 nights
Includes all fees
Image gallery for Amazing Historic Cabin Nestled In The Heart Of Julian Pets ok Quiet and secluded
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Amazing Historic Cabin Nestled In The Heart Of Julian Pets ok Quiet and secluded
Julian, CA
17% off
Price is $186
$186
$1,299 for 7 nights
$1,299 for 7 nights
Includes all fees
Image gallery for The Milky Way Modern Desert Retreat
1010 out of 10 rating
Exceptional
(63 reviews)
The Milky Way Modern Desert Retreat
Borrego Springs, CA
11% off
Price is $707
$707
$4,949 for 7 nights
$4,949 for 7 nights
Includes all fees
Image gallery for Borrego Springs Mid-Century Modern Gem - Step back in time!
9.09.0 out of 10 rating
Wonderful
(9 reviews)
Borrego Springs Mid-Century Modern Gem - Step back in time!
Borrego Springs, CA
9% off
Price is $219
$219
$1,532 for 7 nights
$1,532 for 7 nights
Includes all fees
Image gallery for Studio with private back yard, surrounded by desert.
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Studio with private back yard, surrounded by desert.
Borrego Springs, CA
13% off
Price is $142
$142
$991 for 7 nights
$991 for 7 nights
Includes all fees
Image gallery for Desert Vacation Rental in Borrego Springs, California
9.69.6 out of 10 rating
Exceptional
(39 reviews)
Desert Vacation Rental in Borrego Springs, California
Borrego Springs, CA
13% off
Price is $213
$213
$1,494 for 7 nights
$1,494 for 7 nights
Includes all fees
Image gallery for "The Deer Bungalow" Pine Hills Large Custom Home in Julian that is Pet Friendly
9.89.8 out of 10 rating
Exceptional
(29 reviews)
"The Deer Bungalow" Pine Hills Large Custom Home in Julian that is Pet Friendly
Julian, CA
17% off
Price is $340
$340
$2,382 for 7 nights
$2,382 for 7 nights
Includes all fees
Image gallery for SUMMER LOW MIDWEEK RATES! Charming 2-bedroom cottage in Julian with FREE Wifi
1010 out of 10 rating
Exceptional
(17 reviews)
SUMMER LOW MIDWEEK RATES! Charming 2-bedroom cottage in Julian with FREE Wifi
Julian, CA
8% off
Price is $207
$207
$1,450 for 7 nights
$1,450 for 7 nights
Includes all fees
Image gallery for 2 B/R Most Popular! "Time Traveler Retreat" (Pets Welcome)
9.89.8 out of 10 rating
Exceptional
(47 reviews)
2 B/R Most Popular! "Time Traveler Retreat" (Pets Welcome)
Julian, CA
17% off
Price is $182
$182
$1,271 for 7 nights
$1,271 for 7 nights
Includes all fees
Image gallery for Serene Hilltop Retreat,Jacuzzi,Near Julian DT,Stunning Natural Views&Cozy beds
1010 out of 10 rating
Exceptional
(17 reviews)
Serene Hilltop Retreat,Jacuzzi,Near Julian DT,Stunning Natural Views&Cozy beds
Julian, CA
26% off
Price is $365
$365
$2,556 for 7 nights
$2,556 for 7 nights
Includes all fees
Image gallery for With EV charger -Mid Century Modern Close to Hiking, Golf,&Stargaze on the patio
9.09.0 out of 10 rating
Wonderful
(17 reviews)
With EV charger -Mid Century Modern Close to Hiking, Golf,&Stargaze on the patio
Borrego Springs, CA
9% off
Price is $136
$136
$955 for 7 nights
$955 for 7 nights
Includes all fees
Image gallery for Enjoy peace and privacy in an apple orchard at The Orchard House in Julian, CA
1010 out of 10 rating
Exceptional
(171 reviews)
Enjoy peace and privacy in an apple orchard at The Orchard House in Julian, CA
Julian, CA
9% off
Price is $295
$295
$2,062 for 7 nights
$2,062 for 7 nights
Includes all fees
Image gallery for Cozy Cabin Studio Nestled in the Trees with Mountain Views.
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy Cabin Studio Nestled in the Trees with Mountain Views.
Julian, CA
8% off
Price is $207
$207
$1,446 for 7 nights
$1,446 for 7 nights
Includes all fees
Find spaces that suit your style
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Find the best place to stay - Sky Sailing
Desert Oasis with Pool, Fire Pit, Game Room, and Dry Bar
Sleeps 10 · 4 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
Moonlit Retreat 6 Bedroom Borrego Pool/HotTub Home
Sleeps 16 · 6 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Perfect Desert Getaway
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Welcome to Casa del Carnero - Your Country Club Desert Oasis!
Sleeps 10 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
98 reviews(98 reviews)
Starlit Ranch| Pool and Spa Estate| Sunrise and Sunset Views
Sleeps 20 · 7 bedrooms · 6 bathrooms
8.68.6 out of 10
Excellentexcellent
12 reviews(12 reviews)
Borrego Springs Condo w/ Private Hot Tub & Views!
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
99 reviews(99 reviews)
Top rated rentals - Sky Sailing
Excellent stay
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Very clean and quite house, the best inTown
David J.
Stayed Jul 2025
Beautiful house with stunning views.
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
The house is spacious and comfortable. The views are incredible. The property is private and quiet and just a five minute drive into town. Perfect location. We would definitely stay at the property again. Highly recommend.
Alan I.
Stayed Jul 2025
Perfect!! Just what we needed!!
1010 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
This place is absolutely amazing! Just what the listing said it would be and then some. Stayed here for my girlfriend’s 40th birthday and we couldn’t have asked for anything better. The pool was amazing, the stargazing left us in awe. Truly a perfect getaway!
Aaron M.
Stayed Jun 2025
The best
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
The best place in Borrego Springs.
Marko B.
Stayed Jun 2025
Excellent
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
This is a nice clean apartment. Perfect for a couple. Very much enjoyed my stay. Wolud stay again. 10/10
Kristina F.
Stayed May 2025
Beautiful Casita
1010 out of 10
Exceptionalexceptional
55 reviews(55 reviews)
Rosario was very kind & personable. The little casita is beautifully simple, calm and refreshing! It has everything you need. It felt like a resoet room, which was enjoyable. We even got to see a coyote as we enjoyed breakfast on the terrace.
Cheryl M.
Stayed May 2025
Great stay in Borrego Springs
1010 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
We absolutely loved the house as well as what we experienced in Borrego. The house was quite large and well maintained with beautiful artwork throughout the property. It was extremely quiet an so tranquil in the morning as the sun was coming up. I would definitely stay there again if or when we go back for more star gazing.
Alan K.
Stayed Apr 2025
Excellent!!!
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Really a great property. Bright and open with beautiful desert photos and art. Lots of covered sitting areas overlooking the golf course and pool. Will definitely visit again.
Kurious G.
Stayed Apr 2025
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All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
