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Middletown, San Diego, California, United States of America

Middletown vacation rentals

We found 235 vacation rentals — enter your dates for availability

Discover a selection of 235 vacation rentals in Middletown, San Diego that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $89 per night, and houses and condos are popular options for a stay in Middletown. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

View 89 Houses

Condos/Apartments

View 113 Condos/Apartments

Studios

View 75 Studios

Resorts

View 18 Resorts

Find the best place to stay — Middletown

Waterfront/Perfect Location Close to Little Italy & Downtown. Grill & Free wifi

Sleeps 4 · 1 Bedroom · 1 Bathroom
$179 avg/night
(89)

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

Sleeps 6 · 2 Bedrooms · 1 Bathroom
$261 avg/night
(73)

Private Luxury Resort Home in ♥ of the City - Pool ♥ Spa ♥ Outdoor Lounge ♥ Casa Paradiso

Sleeps 10 · 4 Bedrooms · 3 Bathrooms
$1,010 avg/night
(40)

Custom home with cabana, heated pool, spa and view

Sleeps 6 · 3 Bedrooms · 3 Bathrooms
$500 avg/night
(26)

♥ Luxury Hilltop Retreat in the City - No Expense Spared; Unforgettable Views! ♥

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$481 avg/night
(49)

Sunny San Diego Gem w/ Private Hot Tub & Patio!

Sleeps 4 · 1 Bedroom · 1 Bathroom
$134 avg/night
(32)

Search 235 vacation rentals

Top rated rentals — Middletown
Stayed Feb 2021

Perfect Perfect Perfect!

I don't think we will ever stay anywhere else in San Diego at this point. You are close to food, shops and the beach. If you feel like being lazy and not leaving the house, you will not be sorry. The house is accommodating, huge, and very comfortable...

Corlyn N.
Corlyn N.
Stayed Jan 2021

Excellent hosts and excellent accommodations

We stayed here for two months. The place was clean, nicely furnished and well stocked. We also loved the private yard. We felt very welcomed with our two dogs. The hosts were very nice, easygoing and accommodating. The stove broke unexpectedly and ...

Nadia E.
Nadia E.
Stayed Dec 2020

Amazing San Diego Vacation Spot

We absolutely loved our time here and will definitely be back again. The house is extremely well appointed with anything and everything you could need. It has a spectacular view and the locations offers so many fun activities around it which are open...

Cassandra M.
Cassandra M.
Stayed Dec 2020

Beautiful outside and inside

We really enjoyed out stay here. The backyard and observation deck are amazing as others have noted - we had rain one day but took advantage of everything the rest of the time. The outdoor cushions on the deck dried quickly, which we appreciated sinc...

Katherine F.
Katherine F.

Studio City, CA

Stayed Nov 2020

Good Time

We had a good time here. The reasons for rating certain criteria poorly are because we were given the wrong door code multiple times and were forced to wait out in the cold for a while. The property manager responded immediately and did his best to s...

ALEC B.
ALEC B.
Stayed Nov 2020

Perfect family place

Very amazing place perfect for a larger family getaway Beautiful master upstairs and perfect cozy bedrooms downstairs The extra living space downstairs is perfect for a family My little grandson could not get enough of the basketball court Would ...

Ingrid M.
Ingrid M.
Stayed Oct 2020

Great Host. Awesome location

Walking distance to Little Italy, short drive to beaches with everything you need for the beach. Really nice patio area with Barbecue. Jacuzzi was like none other. Tiffany was a great host and made sure we had everything we needed for a great trip. T...

James J.
James J.
Stayed Jul 2020

Quiet and relaxing!

We really enjoyed our stay here! The house is tucked way back in a quiet neighborhood so its perfect for relaxing. There are a lot of windows so its nice and bright during the day, but still private at night since it's up on a hill. It got a little w...

Jeremy F.
Jeremy F.

San Diego

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How many vacation rentals are available around Middletown, San Diego?

Our 2021 property listings offer a large selection of 235 vacation rentals around Middletown. From 89 house rentals to 113 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Middletown?

Yes, of course. Vrbo has 89 Houses in Middletown. Our other popular types of vacation rentals in Middletown include:

  • Condos/Apartments: 113 rentals available
  • Studios: 75 rentals available
  • Resorts: 18 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cottages and more.

Can I find a vacation rental with pool in Middletown?

Yes, you can select your preferred vacation rental with pool among our 12 vacation rentals with pool available in Middletown. Please use our search bar to access the selection of vacation rentals available.