Pasadena vacation rentals

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Top-rated vacation rentals in Pasadena

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Middle River

4.95 out of 5 average rating, 37 reviews

Waterfront Home with Private Beach, Stunning Views

GraceRating, 5 stars3 weeks ago
We stayed in George’s home to celebrate our father’s 90th birthday and had a lovely time. All rooms were very clean, the beds were comfortable, and the kitchen was fully stocked. The view out back over the water, especially at sunrise, was beautiful. The neighborhood was quiet and safe. Excellent communication and support! Thank you, George!
Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 149 reviews

Waterfront Chesapeake Bay Sunrises w/Private Pier!

EricRating, 5 stars1 month ago
Comfortable and cozy cottage on the water. The back deck and enclosed porch was super nice and the view was amazing. Had it not been so cold during our stay we would have been outside more. Everything was as described and perfect for the two of us and my mom. The dock was easily accessible which was nice. Great stay and close to our Son we were there to visit.
Guest favorite

Home in Deale

4.96 out of 5 average rating, 27 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

JuneRating, 5 stars2 months ago
We had a fantastic stay at this Airbnb! The space was clean, comfortable, and thoughtfully designed, making it perfect for families or a group of friends. The host was incredibly welcoming and responsive, ensuring that we had everything we needed for a relaxing visit. The location was convenient, and the amenities exceeded our expectations. It felt like a true home away from home! We would absolutely book again and highly recommend this place to anyone looking for a memorable and comfortable stay. Thank you for a wonderful experience!
Guest favorite

Home in Rock Hall

5 out of 5 average rating, 83 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

BrileyRating, 5 stars4 weeks ago
Jim has a great spot and was very communicative ahead of our trip. It was a great experience working with Jim, would recommend again.
Guest favorite

Home in Stevensville

4.9 out of 5 average rating, 42 reviews

Beachside Dream

MelanieRating, 5 stars3 weeks ago
BK's home is a gorgeous winter getaway. The architecture is striking, and the wall of windows facing the water made us feel as if we were outdoors, even though we were cozied up on the couch. The area trails are pretty and dog friendly. We enjoyed a gorgeous waterfront sunset while sitting around the backyard fire pit. The house is clean and spacious, and the kitchen was well stocked with pots, pans, and other equipment. The wifi was strong and reliable, too. The beds are comfy and the showers work well. We would definitely return.
Guest favorite

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars1 month ago
The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !
Superhost

Cottage in Saint Michaels

4.84 out of 5 average rating, 31 reviews

Cottage #8 Herons Nest Lg 2 rooms Under Main House

NicoleRating, 5 stars19 months ago
It’s super cute, quaint and has such character. Something for the whole family we will be back.
Superhost

Cottage in Pasadena

4.88 out of 5 average rating, 121 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

AlexaRating, 5 stars2 months ago
A nice stay with family. If you know what to expect it’s a lovely stay. The cottages are small but the scenery is beautiful. A little run down but perfectly fine just for sleeping for a weekend. We did encounter a lot of flies but we were right on the water. Overall a good stay. Definitely visit Tuggies if you love a good dive bar!
Guest favorite

Home in Annapolis

4.99 out of 5 average rating, 67 reviews

Captain’s Retreat! Newly Renovated - Beach House!

MaxRating, 5 stars3 weeks ago
It was a great place for our family Christmas get together. Check in was a bit combersome not being familiar with the Yale Access app but Dan was gracious and unlocked the door remotely. If the need would arise we would definitely stay here again.
Guest favorite

Guesthouse in Arnold

4.88 out of 5 average rating, 16 reviews

Adorable 1 BR guest house with water views, deck

LauraRating, 5 stars3 months ago
Clean and cute and just as described. Perfect for a long weekend away in Annapolis for the boat show!
Guest favorite

Home in Annapolis

4.93 out of 5 average rating, 108 reviews

Historic Downtown House with Off Street Parking

LisaRating, 5 stars1 month ago
Christopher’s place in downtown Annapolis is perfectly located! There are so many great shops and restaurants in walking distance. The off street parking was so convenient. The house itself is so cozy with very comfortable beds and nice towels and linens. The decor is tastefully done and the kitchen was well equipped with everything we needed to cook Thanksgiving dinner. Our family, including our beloved Golden Retriever, had a great time! For others traveling with a dog, just know that the yard is not fully fenced… the walkway by the house is open to the street and the rear yard is connected to a shared parking area…so you will need to keep a close eye on your dog. Overall we were so happy with our stay and would love to stay again. Thanks, Christopher, for sharing your home in one of our favorite places to visit. We will be back!
Guest favorite

Home in Alexandria

5 out of 5 average rating, 13 reviews

A Bold and Relaxing Old Town Xcape

KathrynRating, 5 stars1 week ago
I found the house charming & comfortable. The instructions that Uche provided were easy & he sent along more bits of things to know, just as I needed them. The communication was excellent. I look forward to coming back to this home, soon!

Popular amenities for Pasadena vacation rentals

Stay near Pasadena's top sights

Double T Diner20 locals recommend
Kinder Farm Park13 locals recommend
Marley Station Mall10 locals recommend
Mike's Crab House North10 locals recommend
Anne Arundel Seafood9 locals recommend
Glory Days Grill9 locals recommend

Other great vacation rentals in Pasadena

Superhost

Home in Arlington

4.78 out of 5 average rating, 274 reviews

Newly renovated; mins to DC, airport, food, metro

AlexRating, 5 stars3 days ago
I was a return customer, and will return again! Great hosts, great place to stay! We always enjoy our stay. Top notch!
Guest favorite

Home in Edgewater

4.91 out of 5 average rating, 139 reviews

House in Edgewater Maryland

StephanieRating, 5 stars3 months ago
The place was exactly what we needed. Location was perfect to get to everything we needed and wanted to do. We were able to check in a little bit early, which was amazing and helpful. Would definitely stay again!
Guest favorite

Home in Deale

4.87 out of 5 average rating, 94 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

AmiRating, 5 stars3 weeks ago
Our group had such a lovely time at Shawn's home! The space itself was spacious and absolutely beautiful, even in the dead of winter. There were plenty of spaces to gather or take time alone, which was really important for our group. The kitchen was well stocked, and we had an easy time cooking our meals. The bedrooms were all nice and comfortable, and reflected the listing. Shawn was perfectly communicative and made it easy to contact her when necessary. We can't wait to return!
Superhost

Home in Pasadena

4.85 out of 5 average rating, 54 reviews

Beautiful New Home Near Beach and Patapsco River

VeronaRating, 5 stars1 month ago
House looks even better than the pictures. Very nice, very modern and all amenities were wonderful. I am looking to come back in the summer and enjoy the lovely pool area.
Guest favorite

Apartment in Canton

5 out of 5 average rating, 27 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

KimberlyRating, 5 stars3 weeks ago
Very responsive host. Apartment in fabulous location. In wonderful historic Baltimore house and neighborhood. Minor glitches addressed immediately and easily by host. If you’re looking for something fun and interesting this is it.
Superhost

Townhouse in Fells Point

4.96 out of 5 average rating, 134 reviews

Artsy, Historic Rowhouse with Striking Harbor Views

ThomasRating, 5 stars3 weeks ago
Baltimore! This is an excellent option for stays in the city. Walk the waterfront to Fells Point. Parking is free on Cambridge Street. The property is clean, spacious and has everything you need to make yourself feel at home.
Guest favorite

Home in Arlington

4.97 out of 5 average rating, 92 reviews

Entire family size house steps to ANC & metro walk

KristinRating, 5 stars1 month ago
Wonderful, huge house for my entire family for the holidays! Lots of bedrooms, bathrooms, and space to hangout. Great location, close to DC, shopping, groceries, coffee, parks, and more. Tyler is an attentive, thoughtful host. I would highly recommend!
Superhost

Apartment in North Bethesda

4.67 out of 5 average rating, 64 reviews

Lovely 1-Bedroom rental unit, with great view

TessaRating, 5 stars2 months ago
This was our second time staying here and it’s great! Super clean and always a super easy stay and very great location

Quick stats about vacation rentals in Pasadena

  • Total rentals

    30 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Pasadena?

    Yes! Work meets play with ease at over 20 vacation rentals in Pasadena featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Pasadena?

    Four-legged friends are welcome in Pasadena. Choose from more than 10 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in house rentals in Pasadena?

    Experience the best of Pasadena with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly house rentals in Pasadena?

    Pasadena has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Pasadena have wireless internet?

    Absolutely! We offer over 10 house rentals with wireless internet in Pasadena. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Pasadena have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Pasadena. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Anne Arundel County
  5. Pasadena