Oceanfront Rentals in Windsor Hills, CA: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
  3.  USA

  4.  California

  5.  La Mesa
  6.  Windsor Hills

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84 Best Oceanfront Rentals in Windsor Hills (Starting from $104)

Charming 2 Room La Mesa Casita w/Pool, BBQ & Yard
Charming 2 Room La Mesa Casita w/Pool, BBQ & Yard
Apartment
La Mesa, CA, USA
1.7k from Windsor Hills center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms4 Guests
9.8

Exceptional

8 reviews

$191
Average price / night
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Cozy Casita
Cozy Casita
Apartment
La Mesa, CA, 91942, United States
1.2k from Windsor Hills center

AC, Barbecue, Crib, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area

1 Bedroom4 Guests
9.4

Superb

8 reviews

$170
Average price / night
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Chic Casita w BBQ, Patio, Backyard - 4 min to SDSU, 15 mins to beach, Unit B
Chic Casita w BBQ, Patio, Backyard - 4 min to SDSU, 15 mins to beach, Unit B
House
La Mesa, CA, USA
1.9k from Windsor Hills center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$157
Average price / night
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5br Home with Pool, Hot Tub, BBQ, Putting green
5br Home with Pool, Hot Tub, BBQ, Putting green
House
La Mesa, CA, 91941, United States
1.3k from Windsor Hills center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

4 Bedrooms10 Guests
New to Booking
$673
Average price / night
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Private Pool Chefs Kitchen BBQ 4min to SDSU
Private Pool Chefs Kitchen BBQ 4min to SDSU
House
La Mesa, CA, USA
1.9k from Windsor Hills center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$473
Average price / night
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Entertainers Dream Pool Home
Entertainers Dream Pool Home
House
La Mesa, CA, 91941, United States
2.5k from Windsor Hills center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment

3 Bedrooms15 Guests
9.4

Superb

10 reviews

$858
Average price / night
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Central SD, Luxury Home and Casita, Pool, BBQ, Sleeps10
Central SD, Luxury Home and Casita, Pool, BBQ, Sleeps10
House
La Mesa, CA, USA
1.9k from Windsor Hills center

Luxury, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms10 Guests
New to Booking
$780
Average price / night
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2 Bed 2 Bath 15-20 Minutes to all the Best of San Diego!
2 Bed 2 Bath 15-20 Minutes to all the Best of San Diego!
House
La Mesa, CA, 91942, United States
2.7k from Windsor Hills center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.2

Superb

19 reviews

$175
Average price / night
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Mountain Majesty with AC BBQ Parking
Mountain Majesty with AC BBQ Parking
House
Lemon Grove, CA, USA
2.4k from Windsor Hills center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

2 Bedrooms4 Guests
3.0

Review score

1 reviews

$521
Average price / night
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Luxury Private Oasis- 2 King Suites - Pool-Spa-Fire Pit-Sauna-Arcades-Playground
Luxury Private Oasis- 2 King Suites - Pool-Spa-Fire Pit-Sauna-Arcades-Playground
House
Spring Valley, CA, 91977, United States
3.0k from Windsor Hills center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub

6 Bedrooms41 Guests
10.0

Exceptional

32 reviews

$2009
Average price / night
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San Diego Luxury Oasis
San Diego Luxury Oasis
House
Spring Valley, CA, USA
2.7k from Windsor Hills center

Luxury, Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages

6 Bedrooms30 Guests
10.0

Exceptional

2 reviews

$1349
Average price / night
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Sunny & Spacious 3BR Retreat w/ Parking & A/C
Sunny & Spacious 3BR Retreat w/ Parking & A/C
House
La Mesa, CA, 91942, United States
3.1k from Windsor Hills center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$434
Average price / night
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Mountain Villa in San Diego - Pool & Waterslide, Spa, Pickle Ball, Game room
Mountain Villa in San Diego - Pool & Waterslide, Spa, Pickle Ball, Game room
Villa
La Mesa, CA, USA
3.0k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs

5 Bedrooms12 Guests
New to Booking
$725
Average price / night
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Special Italian Villa, Ocean/Sunset View, Pool, HotTub Near Attractions, Beaches
Special Italian Villa, Ocean/Sunset View, Pool, HotTub Near Attractions, Beaches
House
La Mesa, CA, 91941, United States
3.2k from Windsor Hills center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub

8 Bedrooms26 Guests
10.0

Exceptional

251 reviews

$1775
Average price / night
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Entire Home-Kid Friendly San Diego Retreat
Entire Home-Kid Friendly San Diego Retreat
House
Lemon Grove, CA, USA
3.0k from Windsor Hills center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
New to Booking
$203
Average price / night
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Lush GuestHouse in Serene Mount Helix
Lush GuestHouse in Serene Mount Helix
House
Spring Valley, CA, 91977, United States
3.5k from Windsor Hills center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
9.6

Exceptional

25 reviews

$146
Average price / night
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Tropical Retreat with Pool and Spa in La Mesa
Tropical Retreat with Pool and Spa in La Mesa
House
La Mesa, CA, USA
3.5k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis

5 Bedrooms16 Guests
New to Booking
$1637
Average price / night
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Quite Peaceful Mountain Retreat
Quite Peaceful Mountain Retreat
House
La Mesa, CA, 91941, United States
4.1k from Windsor Hills center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.4

Superb

10 reviews

$220
Average price / night
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Stunning 4-bedroom, 3-bath home with a 2-bedroom, 1-bath guest house, featuring a pool, spa, game room, and scenic views!
Stunning 4-bedroom, 3-bath home with a 2-bedroom, 1-bath guest house, featuring a pool, spa, game room, and scenic views!
House
San Diego, CA, USA
3.8k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis

7 Bedrooms15 Guests
New to Booking
$849
Average price / night
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This warm and welcoming Home can be your Home away from Home
This warm and welcoming Home can be your Home away from Home
Condo
Spring Valley, CA, 91977, United States
4.1k from Windsor Hills center

AC, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$104
Average price / night
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SanDiego Insider's Coastal Bliss and Urban Wonders. Near SDSU  Chollas Lake.\n\n\n\n
SanDiego Insider's Coastal Bliss and Urban Wonders. Near SDSU Chollas Lake.\n\n\n\n
House
San Diego, CA, 92115, United States
4.2k from Windsor Hills center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.4

Superb

19 reviews

$269
Average price / night
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*NEW*secluded/studio/getaway/sunset/mountain view + patio
*NEW*secluded/studio/getaway/sunset/mountain view + patio
Apartment
Spring Valley, CA, 91977, United States
4.2k from Windsor Hills center

Arcade, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
8.0

Good

1 reviews

$156
Average price / night
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Spacious & Fun - 5BR/4BA • Pool Table • Hot Tub
Spacious & Fun - 5BR/4BA • Pool Table • Hot Tub
House
El Cajon, CA, 92020, United States
4.7k from Windsor Hills center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms15 Guests
10.0

Exceptional

18 reviews

$889
Average price / night
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Cozy, Spacious, Family-Friendly + LARGE YARD W/ HOT TUB ~by all attractions!\n
Cozy, Spacious, Family-Friendly + LARGE YARD W/ HOT TUB ~by all attractions!\n
House
San Diego, CA, 92115, United States
4.7k from Windsor Hills center

AC, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms10 Guests
9.8

Exceptional

12 reviews

$367
Average price / night
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4 Bd Hillside Sanctuary |  Peaceful Retreat Near SDSU & Hiking
4 Bd Hillside Sanctuary | Peaceful Retreat Near SDSU & Hiking
House
San Diego, CA, 92120, United States
4.8k from Windsor Hills center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
8.8

Fabulous

8 reviews

$354
Average price / night
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Entertainment paradise with TWO houses and a pool in Central San Diego
Entertainment paradise with TWO houses and a pool in Central San Diego
House
San Diego, CA, 92105, United States
4.9k from Windsor Hills center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

5 Bedrooms16 Guests
7.6

Good

4 reviews

$969
Average price / night
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Close to Beaches, Spectacular Views w/hot tub
Close to Beaches, Spectacular Views w/hot tub
House
El Cajon, CA, 92020, United States
5.1k from Windsor Hills center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$511
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Oceanfront Rentals in Windsor Hills.

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Windsor Hills Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 84 verified oceanfront rentals in Windsor Hills. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Windsor Hills vary depending on the property size, exact beachfront location, and season. Rates typically start from around $104 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Windsor Hills offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Windsor Hills welcome pets. Currently, 37 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Windsor Hills often include features designed for a comfortable coastal stay, such as Oceanfront, View, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.