Discover a selection of 318 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 gardens and backyards. Prices start at $110 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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Top rated rentals — Middletown
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What are the top vacation rentals in or near Middletown?

Whether you're seeking a cozy retreat for you and your special someone or somewhere spacious to fit the family, you'll find some top vacation rentals in and around Middletown. Here are a couple to get you inspired:

  • "Balboa Park Super Luxe Tropical Hideaway Minutes To The Zoo" is popular with guests. Around 3 miles from Middletown, it has 2 bedrooms and lots of useful amenities, including a nearby zoo and off-street parking options.
  • "Kennebeck Ct, 30 Seconds To Sand" also promises an awesome stay, offering 3 bedrooms, a dining table, a stair gate and more. It's around 5 miles from Middletown.

For even more great options, use the search bar at the top of the page to find the perfect Middletown vacation rental for you.

What are the best tiny house vacation rentals in or near Middletown?

For an unforgettable experience, book a tiny house rental in Middletown. A word of warning though — after you've experienced the tiny house lifestyle, the urge to move into one of these pocket-sized digs will be hard to resist!

  • Escape from the world and disappear to "Travelers Tiny Home Oasis With Private Hot Tub". This retreat in San Diego packs plenty of comforts into its compact space, such as cookware, dishware and utensils and an electric kettle.
  • Alternatively, settle in at "Tiny House In The Clouds, Perfect For Couples". Located in Grant Hill, this tiny abode comes with heating and a separate dining area.

What are the top-rated vacation rentals for weekend getaways in or near Middletown?

Forget about those chores, because weekends were made for having fun. Settle into one of these weekend getaways in and around Middletown and enjoy all the fantastic things to do nearby:

  • Located 1 mile to the north of the center of Middletown, "Fort 1 Craftsman On The Woods - Quiet" is a good match for nature lovers and adventurous types. Get out and explore nearby attractions, including Queen Califa's Magical Circle and Kate Sessions Memorial Park. Then, try your hand at activities like fishing or surfing and boogie boarding.
  • "Right On The Beach Exquisitely Remodeled 3br" is another great property to consider. Around 5 miles northwest of Middletown, use it as a base to try some golf or sailing. B Street Cruise Ship Terminal and Tijuana Estuary Nature Preserve also have to be on your must-do list if you stay here.

Can I find studio apartments for rent in and around Middletown?

Studio apartments set a high bar when it comes to location and convenience. Check out these studio apartments for rent in or near Middletown and experience a slice of the local vibe and energy:

  • Unpack your bags at "Treetop Luxury Suite At Tropical Resort". Amenities including an oven and a smart TV will help you feel at home here.
  • Another popular choice is "50' From Ocean - Amazing View - Private Cottage". Make use of an oven, internet services and other convenient amenities during your getaway.

There are loads of attractions around Middletown to add to your agenda. Feed the culture lover in you and visit Copley Symphony Hall and Museum of Photographic Arts.

Can I find short term rentals in or near Middletown?

You'll find a selection of short-term rentals in and around Middletown. And the good news is, Vrbo has something for all budgets and styles — from generous-sized homes big enough for the whole family to cute lodges ideal for a romantic getaway. Here's a selection of what's available in Middletown:

  • Located close to the heart of Middletown, "100 Five Star Reviews For A Reason. 1700sf 3br" is perfect for a short escape. Use it as a base to visit nearby attractions including San Diego Zoo.
  • Or maybe "Bright 1735 Sf, 2 Suits. Centrally Located From The Bay To The Sea In Min’s" suits you better. Visit nearby sights such as San Diego Convention Center during the daytime and then rest and relax in your comfy rental at night.

What are the best romantic weekend getaways in or near Middletown?

Forget chocolates and roses. Sometimes all you need is to get away for a weekend, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Middletown that would make even Cupid swoon. Here are some we think you'll be enamored with:

  • Sneak off on Friday for a few passion-filled nights at "Balboa Park Super Luxe Tropical Hideaway Minutes To The Zoo". Located around 3 miles from Middletown, it comes with lots of nice touches, like a fireplace and outdoor furniture.
  • "Kennebeck Ct, 30 Seconds To Sand" is another popular option that's bound to impress. It's approximately 5 miles from Middletown and comes with a nearby bay and winery tours.

Are there mansions for rent in or near Middletown?

We've got some superb mansions for rent in and near Middletown. If you're on the lookout for somewhere with lots of space as well as wow factor galore, these stunners will tick all your boxes:

  • Around 1 mile to the east of Middletown is "New Stunning Mansion Amazing Location". As well as its grand design, you'll also love its top-notch amenities, such as golf and beauty services.
  • With golf, beauty services and loads of other top-notch amenities, "San Diego's Tuscan Villa Mansion On The Beach" will get your guests' tick of approval. This opulent stay is roughly 6 miles to the northwest of Middletown.

What are the best large group vacation rentals in or near Middletown?

Share your trip and boost your odds of having fun. Whether you're planning an adventurous escape with your besties or a big family gathering, you'll have your pick of large group vacation rentals in and around Middletown:

  • You'll have enough room to move at "A Rare Find In Northpark". Around 3 miles east of Middletown, this grand property has 5 bedrooms that sleep up to 12 guests. Quality amenities include a garden and a kitchen.
  • Nothing takes priority over spending time with the people you love, and "Storybook House 2 Blocks From Ocean Or Mission Bay" is the perfect place to do that. Located around 6 miles to the northwest of Middletown, as many as 12 people can stay in this vacation rental which has 5 bedrooms. An ocean view and a water park are among the many amenities here.

What are the best houses for rent with a pool in or near Middletown?

From energetic games of follow the leader to quiet morning dips, a pool promises fun for both kids and adults. Score major brownie points with the fam by renting a house with a place to swim in or near Middletown:

  • Make pool day every day at "Prime View Location, 1 - House Back From Boardwalk Traffic". A kitchen island and a barbecue grill are a couple of the other amenities that help make this place so appealing.
  • "Storybook House 2 Blocks From Ocean Or Mission Bay" is another sought-after option. After you've enjoyed a refreshing dip with the fam, make use of other conveniences like towels and beach sun loungers.

What are the best large family vacation rentals in or near Middletown?

Whether your ideal getaway is high in the hills or near the beach, you'll enjoy it even more if you share it with people you love. Settle into one of these large family vacation rentals in or near Middletown and bring the whole gang along:

  • Sleeping up to 10 guests in 3 bedrooms, "Kennebeck Ct, 30 Seconds To Sand" is the perfect place to hang out with the family. This top-rated getaway is 5 miles to the northwest of Middletown and has creature comforts that include a porch and childrens activities.
  • "Right On The Beach Exquisitely Remodeled 3br" is another popular option. It's around 5 miles to the northwest of Middletown, has 3 bedrooms and can accommodate up to 8 people. Handy amenities here include a dishwasher and coffee and tea making facilities.

When you want to explore your surroundings, there are lots of family-friendly attractions nearby to keep everyone entertained and happy. San Diego Zoo, Hotel Circle and Belmont Park should be at the top of your itinerary.