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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

***Romantic View Home Centrally Located in Windsor Hills, La Mesa***

Bedrooms 3
Space 1,400 sq ft
Property type house
Minimum Stay 4 nights


About the property

Newly remodeled 2B/2B-House 1,000sf +1B/1B 400sf Guest Flat.

Beautifully remodeled and newly furnished home in lovely Windsor Hills, centrally located in San Diego high above Downtown La Mesa. This romantic space consists of l,400 sq. ft. total with three bedrooms, three full baths, kitchen plus kitchenette, dining room, large living/family room, central heating/air-conditioning, garage, and Brand New LG Front Loader Washer/Dryer.



MAIN HOUSE (1-5 guests), GUEST HOUSE (1-3 guests),


Upper House - 1,000 sq. ft., 2 bedroom, 2 bathroom, kitchen, dining room, living room with two conversation spaces, beautiful deck with view.

Guest House - 400 sq. ft., 1 bedroom, 1 bath (shower),

kitchenette, lounging space and deck access with view!

The Main House with Wood floors and Vaulted Wood-Beamed Ceilings add vintage charm along with original doors, cabinetry and closets. 55-inch Flat-Screen Television in living room can be viewed in the open floor plan from kitchen and dining areas.

The Master Bedroom includes Queen Bed with brand new comfortable mattress, Master Suite Bath, 32-inch Flat-Screen T.V., Mirrored Closet and Spectacular Coastal Views, Awesome Sunsets, and Sparkling City Lights.

The second Bedroom includes a Queen Bed, Armoire with Drawers, T. V., and Closet...a bright space with windows to enjoy the warmth and beauty of wonderful sunny San Diego.

Guest House/Third Bedroom boasts a King-size Bed, Two- 32-inch TVs with view windows in a 400 sq. ft. space to include Bathroom, Kitchenette and Lounging area. Flooring consists of beautiful Italian Porcelain Tile throughout this cozy setting...a great place to hang out and relax inside...or on the outside deck!

This Guest House may be reserved in conjunction with the two bedroom/two bath Main House...or it may be reserved by itself. Speak with owners for personal reservation accommodations and pricing.

The Main House can be reserved by itself also.

The charming home accommodates 6 people in beds with two roll-outs available for extra sleeping arrangements.

This gem is located in a quaint upscale cul-de-sac neighborhood with spectacular views in the distance of the Pacific Ocean, San Diego Harbor, San Diego Coastline, and Sparkling City Lights from nearly all rooms and 2 outside decks. Sunsets are absolutely amazing!

This Jewel is in a great walking neighborhood...which boasts the very popular 'Secret Stairway' that begins at the top of the mountain and leads you all the way down into the La Mesa Village.

More Details

Member since: 2014
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
April 24, 2018

Why Carla chose Windsor Hills

We chose this Windsor Hills Property mainly for its charm, romantic views and dazzling sunsets. This "Jewel" boasts wood-beamed ceilings in the " Main House" (2b/2b), two outside decks, dining room, retro kitchen, and a large living space overlooking the coast.

Also a "Guest House" with kitchen, living space, bathroom (shower) and bedroom (l) which can be rented along with the Main House for overflow of guests.

The La Mesa area is in a great location and very central to so many activities through San Diego.

What makes this house unique

Our "Jewel in the Hills" Vacation Home and Guest House is in an awesome, quiet, walking neighborhood with the "Secret Stairs" that take visitors to the bottom of the mountain (or to the top of Windsor Hills) where guests can stroll into La Mesa Village for some shopping, dining, antiquing...and much more. Trolley access is available in La Mesa Village for access around San Diego and the Mexican Border.

Guestbook comments from the owner

Beautiful vacation spot. People who stay at this property will realize they are in a central area of San Diego between the east and the west (at the ocean). Wonderful views of the San Diego city line, valley, and water all from the deck that extends from the living room.

Very comfortable, nice kitchen, bedrooms, and bathrooms. The house is located in a neighborhood that has the advantages of places to walk, ride, and wonderful neighbors. I've used this house on two separate occasions and have been extremely satisfied with the amenities, including a television in the living room and every bedroom. It has a great living room, dining area, decks, and artwork throughout (French-themed).

Great location, amenities, and lots of things to do in just a short walk away or even a quick drive to many of San Diego's great attractions.
May 2014
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Windsor Hills House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 1400 sq ft
House Rules:
  • Max. occupancy: 8
  • Minimum Age Limit for Renters ...
  • pets not allowed
  • non smoking only
Location Type:
  • Downtown
  • Ocean View
  • Village ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer ...
  • Garage ...
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking ...
  • Towels Provided
  • Washing Machine ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Room
  • seating for 6 people
  • 3 Bathrooms
  • Bathroom 1 - toilet , combination tub/shower , Newly remodeled with tiled floor and shower.
    Bathroom 2 - toilet , combination tub/shower , Beautifully remodeled full bathroom with tiled floor/shower.
    Bathroom 3 - toilet , shower , Beautifully remodeled with tiled shower/granite counter.
  • 3 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 queen , Great View! Comfortable new mattress, 32in TV, closet alarm
    Bedroom 2 - 1 queen , New mattress. Access to hall bathroom. 32in TV, Armoire
    Bedroom 3 - 1 king , Cozy New Mattress, 32in TV, Separate Kitchenette View
  • All the bedrooms are bright with windows and views. Bedroom #1 has mesmerizing view, mirrored closet, master bath off of room and 32in flatscreen TV. Bedroom #2 has great closet space, access to hall bathroom, and 2 windows for a bright space. Bedroom #3 is part of a 400 sp. ft. space with two closets, kitchenette, bath with shower and Italian Porcelain Tile. View window.
  • Books
  • Games
  • Satellite / Cable ...
  • Television ...
  • Deck / Patio ...
  • Outdoor Grill
  • Long-term Renters Welcome
  • wheelchair inaccessible
  • botanical garden
  • churches
  • cinemas
  • duty free shops
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
  • theme parks
  • water parks
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • gambling casinos
  • horseback riding
  • miniature golf
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • shuffleboard
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • hot air ballooning
  • ice skating
  • jet skiing
  • kayaking
  • mountain biking
  • parasailing
  • pier fishing
  • racquetball
  • rock climbing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
We provide beach chairs and beach towels for quick trips to the ocean!


Exceptional! 5/5 -
(42 traveler reviews)

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***Romantic View Home Centrally Located in Windsor Hills, La Mesa***
average rating of 4.9761906 based on 43 reviews
Fort Worth , TX USA

The "Jewel in the Hills" gets a Precious Ruby

  • 5 of 5

We came to San Diego to visit with our Grandson and GreatGrandchildren and had the good fortune of finding the “Jewel in the Hills”. We stayed for several nights and I give it a Ruby...Rubies are one of the most precious stones in the entire world. You can walk into the “Jewel in the Hills” and feel like you walked into your own home. Everything was so clean and very comfortable and had all the amenities of home.

Upon arrival we were greeted with a warm hug from Carla and a big smile from John. There was a basket of fruit, cookies and goodies for our GGrandchildren who came over for visits. A Marie Callender’s famous pie (Apple). I loved that we had so much open space. To walk out on the balcony was a treat anytime of the day and evening. You could see all the homes below as we were up on a hill. The view at night was incredible.

I am an artist and was glad to see a big clean garage where I could set up a printmaking workshop for the children. I brought one folding table and Carla delivered another. Also room enough for a hopscotch made with duck tape.

If you are searching for a Jewel of a place to spend time and explore the area this is it.... when we return to San Diego to visit we will certainly want the opportunity to stay at the “Jewel in the Hills”.

Carla and John will make you feel very special.

  • Submitted: Nov 12, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
Owner's Response: Our "Jewel in the Hills" Vacation Home and Guest House is especially set up so that you and your family feel at home....away from home! Our goal is to provide the most comfortable stay along with the necessary amenities and space to enjoy your family. The view is spectacular of the surrounding neighborhoods and the stunning sunsets along the distant coast. On a clear day one can see the ships on the water at Point Loma! Perfect space for the perfect family!!!
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Perfect for the whole family.

  • 5 of 5

Beautiful views and well-maintained.

  • Submitted: Aug 20, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Perfect getaway!

  • 5 of 5

Definitely a home away from home! Carla and John added so many nice touches that made us feel very welcome. They also went above and beyond by getting my girls a birthday cake for our arrival (we were in San Diego to celebrate their bdays!) The home itself was very comfortable and accommodating for our family of 4 adults and 3 kids. We were able to cook meals and even BBQ without being in need of anything! The views were stunning, we enjoyed sitting on the balcony and watching the sunset or sitting out there in the early morning and watching the hummingbirds fly by. We had an amazing time and are looking forward to coming back!

  • Submitted: Jul 23, 2017
  • Stayed: July 2017
  • Source: HomeAway
Owner's Response: Such a pleasure meeting all of you! John and I were so happy you enjoyed our "Jewel of the Hills" Vacation Home and Guest House and look forward to your return! Glad you were able to visit the San Diego Zoo, Pt. Loma Lighthouse, beaches, and the very exciting Comic Con...and much more. Give us a call next trip to San Diego and we will lead you to lots of other fabulous sites around the area. Thank you! John and Carla
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Jewel of the Hill ...

  • 5 of 5

Is a real gem. Beautiful sunsets, peaceful mornings, friendly neighbors, comfortable furnishings and delightful hosts. This will be my choice of a place to stay whenever I am back in San Diego. Thank you, Carla and John for this delightful home. I look forward to visiting with you again and again.

  • Submitted: Jun 1, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
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Our home away from home!

  • 5 of 5

My husband and I spent three months at Carla's house this past winter. I usually don’t write reviews but because our experience there was so exceptional I wanted to share it. Carla and John are thoughtful and welcoming hosts. We arrived after a long flight. Of course I was apprehensive, but as soon as I saw the Christmas tree, loaded with lights and decorations, I knew we were in the right place.The neighbors are friendly, the area is quiet and private and the view is unreal. We could have been in Italy. Everything is top drawer which is what I expected because Carla pays close attention to the smallest detail and has furnished the house with only the best. Grocery stores, drug stores and even big box stores are all minutes away. There are three televisions with premium stations. Downstairs there is a lovely guest apt. that I used as an office. It’s fully equipped with kitchen, bedroom and bath and even a 4th TV!!. I can’t wait till next year !

  • Submitted: Apr 24, 2017
  • Stayed: November 2016
  • Source: VRBO, from HomeAway
Owner's Response: We are so pleased once again you've enjoyed your extended stay in our "Jewel in the Hills" Vacation Home and Guest House! John and I look forward to your return this July, 2017...and then again in December 2017 through March 2018 as you travel from New York to sunny San Diego. The Guest House adorns two in the bedroom and in the main living space, for a total of five throughout the property! Our "Jewel" in Windsor Hills sets high on the mountain to give you those beautiful views along the distant coast, and is conveniently close to shopping, dining, and walking. Try the new upscale restaurant in La Mesa Village...Farmers' Table. It's delicious! :) See you soon as you celebrate your daughter's wedding and the " Fourth of July!"
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Beautiful Home - Excellent View - Wonderful Hosts

  • 5 of 5

What a wonderful home with excellent views, convenient location, very well outfitted, and wonderful hosts. Carla and John are simply wonderful! The recent renovations to the very clean and nicely decored home are very well done and the extras that Carla provides (upgraded linens, snack basket, fruit, soaps, hair dryer, bottled water, coffees, etc.) make it feel like "home". The upper floor accommodation is at street level with convenient parking and is well suited for people with disabilities. Additionally, they are excellent guides and sources of area information - - really special folks. The home is conveniently located within walking distance of the Village of LaMesa with "fun walks" at your doorstep. We highly recommend "The Jewel of the Hills" and will definitely stay again.

  • Submitted: Apr 1, 2017
  • Stayed: March 2017
  • Source: VRBO, from HomeAway
Owner's Response: We are so pleased you enjoyed our "Jewel in the Hills" Vacation Home. Such a pleasure visiting with you, Teri, Jennifer, and Jude! Jim, thanks for reserving our spot in La Mesa Village at the great Farmer's Table...the restaurant was "out of this world" good. All of us ladies we're impressed! We look forward to accommodating both you and your beautiful wife, Teri, during future visits to La Mesa.
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Car: recommended

Our lovely owner-operated home in Windsor Hills is centrally located in San Diego County, minutes from the beaches...or the mountains! A short walk to La Mesa Village down the popular 'Secret Stairway' is a convenient path to access a variety of restaurants, shops, antique stores, local coffee/deli hangouts, entertainment, Friday Farmers Market...and much more!

This relaxing space within walking distance to the Trolley gives you access to many sites throughout San Diego--

Qualcomm Stadium, Petco Park, S. D. State University, Grossmont Shopping Center, Fashion Valley and Mission Valley Shopping Centers, movie theaters and restaurants. Ride the trolley to Downtown San Diego Gas Lamp District, Outlet Stores, Tijuana, Mexico, Liberty Station, and Historical Old Town below the Presidio Mission and Park.

During the Fall, Oktoberfest is one of the highlights of La Mesa Village, 'Jewel of the Hills.' For those interested in visiting the San Diego Convention Center for world-famous events such as the COMIC CON CONVENTION, our place is conveniently located just a short distance from those areas whether you choose to drive...or take the trolley! Freeways are within a half-mile distance from this romantic vacation get-a-way. Easy and quick travel to all attractions such as beaches, San Diego Zoo, Sea World, Scripp's Aquarium in La Jolla, Belmont Park in Mission Beach with one of the oldest wooden roller coasters, Coronado Island, and Balboa Park/Museums (prelude to it's Centennial Celebration, with more museums than any other park in America!).

Less than an hour-and-a-half drive to Disneyland in Anaheim, CA, or Knott's Berry Farm makes for a perfect day trip up the coast! Or take a leisurely drive to the mountain town of Julian, famous during the gold rush days of past, and specifically well known for their apple orchards and yummy 'apple pies.' (:

We love to get away on the weekends and spend time visiting the many restaurants in the La Mesa Village.

San Filippo' Pizza, Swamis, BO beau's Kitchen, and Tamarind Thai Restaurant are among the many eateries frequented by the locals and visitors.

Lounge on any of the two decks, sit back, enjoy a

cup of freshly brewed coffee while savoring the breathtaking view of the the coastline and city. Sit

eye level with hummingbirds, sparrows, butterflies,

and hawks as they soar by or perch on the oak tree

near the decks.

Fireworks can be seen at various locations in the city and along the coast on the Fourth of July and other special events.

This shangrilla is nestled on a vantage point in a most private and peaceful setting. Great area for walking or jogging with choices of different routes you can take, and varying degrees of challenge. For more adventurous hiking, visit nearby Mission Trails Park or Cowles Mountain.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning $160
Admin Fee $25
Refundable damage deposit $500

Rates are subject to change. Please call 619-954-5286 for customized quote/circumstances. Groups as large as 8 people, or as small as 1-2 persons can be accommodated. Rent the House 2bed/2bath alone or with Guest Flat, or rent Guest Flat alone.
Main House $245.00 per night, Guest House $130.00 per night
Main and Guest Houses together, $245.00 + $130.00 = $375.00 per night/up to 8 people. Speak to owner for special rates/circumstances.

$500.00 Refundable Security Deposit/ Property Damage Protection of $1,500.00 coverage for a fee of $49.00.

Owner's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.

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