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Our top choices for Middletown Station vacation homes

*Charming* Family & Couples Friendly 4 BR ENTIRE HOUSE

*Charming* Family & Couples Friendly 4 BR ENTIRE HOUSE
Bankers Hill
9.6 out of 10, Exceptional, (61)
"Great house for my brother's and I to enjoy San Diego with our families."
United States
David W.
*Charming* Family & Couples Friendly 4 BR ENTIRE HOUSE

Gorgeous Chalet in historic San Diego's premier neighborhood- Mission Hills!

Gorgeous Chalet in historic San Diego's premier neighborhood- Mission Hills!
Hillcrest
10.0 out of 10, Exceptional, (47)
"Great stay"
United States
marc l.
Gorgeous Chalet in historic San Diego's premier neighborhood- Mission Hills!

1920's Remodeled Craftsman Bungalow Little Italy

1920's Remodeled Craftsman Bungalow Little Italy
Downtown San Diego
7.6 out of 10, Good, (5)
"We needed a small and fast getaway for an event I was going to and the owner was able to accommodate and help us with whatever we needed. The owner was quick to answer and communicate with us when we had questions and was overall nice. The place was small and cute, exactly what we were looking for! Bed is so comfy, the pull out bed for the sofa was easy to pull in and out, a lot of space for our clothes. Kitchen was so adorable. Finding the place overall was very easy since it was right off the...
United States
Elioenai A.
1920's Remodeled Craftsman Bungalow Little Italy

Adorable Quirky Hideaway~BIG Private Enclosed Yard

Adorable Quirky Hideaway~BIG Private Enclosed Yard
Hillcrest
9.2 out of 10, Wonderful, (45)
"Great affordable place, area is filled with restaurants, responsive host. "
United States
Arthur L.
Adorable Quirky Hideaway~BIG Private Enclosed Yard

*FULL REMODEL* 4 BD Entire House Located Close to Downtown!

*FULL REMODEL* 4 BD Entire House Located Close to Downtown!
Bankers Hill
9.8 out of 10, Exceptional, (33)
"It was a nice place to stay especially for families. We have four boys ages 6, 5, 3, and 1. We were worried that our little one wasn't going to be able to sleep through the night in an unfamiliar place, but it worked out fine. The stay was perfect for our family. Had everything we needed. Owner was great with communications when we had questions."
United States
anthony v.
*FULL REMODEL* 4 BD Entire House Located Close to Downtown!

Luxurious 4200 Sq Ft 6 Bedroom Mediterannean Villa

Luxurious 4200 Sq Ft 6 Bedroom Mediterannean Villa
Middletown
10.0 out of 10, Exceptional, (22)
"Property was beautiful and location was close to airport. The floors could've been cleaned a little better, though overall our stay was very enjoyable and would recommend to others."
United States
Shawna F.
The price is AED 1,967
AED 4,254 total
includes taxes & fees
22 Dec - 23 Dec
Luxurious 4200 Sq Ft 6 Bedroom Mediterannean Villa

BBQ Grill, 5 mins to DT, Canyon Views, Parking

BBQ Grill, 5 mins to DT, Canyon Views, Parking
Hillcrest
9.8 out of 10, Exceptional, (172)
"Great location. Just what we wanted "
United States
Christine S.
BBQ Grill, 5 mins to DT, Canyon Views, Parking

Family-friendly 3bd / 2bh with outdoor and dining in SD's best location

Family-friendly 3bd / 2bh with outdoor and dining in SD's best location
Bankers Hill
9.6 out of 10, Exceptional, (65)
"This place felt incredibly cozy, was in a great location and was very clean."
United States
Mayra L.
The price is AED 826
AED 1,908 total
includes taxes & fees
22 Dec - 23 Dec
Family-friendly 3bd / 2bh with outdoor and dining in SD's best location

Robinson-Newly Renovated Beautiful Retreat-Close to ALL

Robinson-Newly Renovated Beautiful Retreat-Close to ALL
Hillcrest
9.8 out of 10, Exceptional, (16)
"Beautiful, spacious home in a great location close to major attractions and local restaurants. Would definitely stay again!"
United States
Dana B.
Robinson-Newly Renovated Beautiful Retreat-Close to ALL

4046 · Modern condo in Hillcrest/Mission Hills

4046 · Modern condo in Hillcrest/Mission Hills
Hillcrest
9.6 out of 10, Exceptional, (25)
"Really beautiful condo within walking distance to many restaurants,bars,shops. Great location. Highly recommended this place."
United States
CJ D.
4046 · Modern condo in Hillcrest/Mission Hills

♥ Best Value in SD! $1M Views; Great Location; Award Winner ♥

♥ Best Value in SD! $1M Views; Great Location; Award Winner ♥
Middletown
9.6 out of 10, Exceptional, (139)
"Great location, very clean and everything was made very easy by the hosts to check in and check out. we definitely recommend staying at this property."
United States
John
♥ Best Value in SD! $1M Views; Great Location; Award Winner ♥

Heart & Soul of San Diego in Old Town. Private heated pool & Jacuzzi NEAR ALL.

Heart & Soul of San Diego in Old Town. Private heated pool & Jacuzzi NEAR ALL.
Old Town San Diego
9.8 out of 10, Exceptional, (22)
"The property has lots of bedrooms, bathrooms, and space for a large group. The backyard is a great space for entertaining. Would highly recommend this spot!"
United States
Matthew R.
Heart & Soul of San Diego in Old Town. Private heated pool & Jacuzzi NEAR ALL.

Luxury 5BD/4BA Mission Hills/Stunning Rooftop + Skyline Views

Luxury 5BD/4BA Mission Hills/Stunning Rooftop + Skyline Views
Mission Hills
9.4 out of 10, Exceptional, (211)
"Great location and great views. We enjoyed the house. "
United States
Mark S.
Luxury 5BD/4BA Mission Hills/Stunning Rooftop + Skyline Views

Modern House In The Hills | Killer Location!

Modern House In The Hills | Killer Location!
Middletown
7.8 out of 10, Good, (6)
"Clean room but wasnt able to reach the host before i arrived.Parking was a liitle challenging."
United States
Keith A.
The price is AED 1,120
AED 1,485 total
includes taxes & fees
13 Jan - 14 January 2026
Modern House In The Hills | Killer Location!

Spanish Villa, Skyline & Ocean Views, Pool Hot Tub

Spanish Villa, Skyline & Ocean Views, Pool Hot Tub
Middletown
8.0 out of 10, Very Good, (5)
"Place was super clean and had every amenity you could need. Pictures don’t do this place justice. "
United States
Michael C.
Spanish Villa, Skyline & Ocean Views, Pool Hot Tub

2 bed, Just a few Minutes to Airport & Old Town, Great City Skyline Views

2 bed, Just a few Minutes to Airport & Old Town, Great City Skyline Views
Mission Hills
6.8 out of 10, (8)
"Me and my girlfriend stayed here for a weekend to kind of just enjoy not having to be home for a weekend and staying here was very nice; the view from the living room and balcony was amazing, was close to all the hotspots in SD and just felt like a second home. I was a bit of a chaotic guest leading up to the check-in and that is because of my work but the host Daniel was very helpful and patient with my mistakes and I appreciate what he did for us."
United States
Nico E.
The price is AED 632
AED 1,502 total
includes taxes & fees
15 Dec - 16 Dec
2 bed, Just a few Minutes to Airport & Old Town, Great City Skyline Views

Avalon III by Avantstay Mins to Gaslamp, Zoo & Airport Beautiful Deck w/ BBQ

Avalon III by Avantstay Mins to Gaslamp, Zoo & Airport Beautiful Deck w/ BBQ
3.5 star property
Middletown
Avalon III by Avantstay Mins to Gaslamp, Zoo & Airport Beautiful Deck w/ BBQ

San Diego Swimming Pool on Stunning Canyon in Hillcrest Mission Hills -Walkable!

San Diego Swimming Pool on Stunning Canyon in Hillcrest Mission Hills -Walkable!
Hillcrest
9.8 out of 10, Exceptional, (65)
"We all loved the property. It was set up very well with everything you would need for a family gathering. The pool is excellent and it was worth the costs to heat the pool. I love the neighborhood and the "
United States
Tricia B.
San Diego Swimming Pool on Stunning Canyon in Hillcrest Mission Hills -Walkable!

Spacious 6-bedroom house in lovely San Diego with AC, WiFi

Spacious 6-bedroom house in lovely San Diego with AC, WiFi
Bankers Hill
The price is AED 3,045
AED 5,777 total
includes taxes & fees
13 Jan - 14 January 2026
Spacious 6-bedroom house in lovely San Diego with AC, WiFi

2 bd w/ yard in heart of Old Town-- WE LOVE PETS! Check our Insta @oldtownvacay

2 bd w/ yard in heart of Old Town-- WE LOVE PETS! Check our Insta @oldtownvacay
Old Town San Diego
10.0 out of 10, Exceptional, (193)
"Amazing stay highly recommended "
United States
Saket B.
The price is AED 808
AED 1,029 total
includes taxes & fees
15 Dec - 16 Dec
2 bd w/ yard in heart of Old Town-- WE LOVE PETS! Check our Insta @oldtownvacay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Station Hotel Reviews