Vacation rentals in Pasadena

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Top-rated vacation rentals in Pasadena

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

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Guest favorite
An open layout living area features a kitchen equipped with stainless steel appliances and a breakfast bar with high stools. A dining table is visible in the background near large windows. The space is complemented by two leather couches and light hardwood flooring.
Home in Arnold
4.94 out of 5 average rating, 108 reviews

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

Guest favorite
A modern kitchen features a large island with bar seating and granite countertops. Stainless steel appliances and a six-burner gas range are present. Soft natural light filters through a window, illuminating a cozy living area with a comfortable sofa and decorative accents.
Guest suite in Glenelg
4.98 out of 5 average rating, 129 reviews

Lovely guest house with gourmet kitchen & King bed

If you're looking for a quick getaway or a brewery hopping good time we offer that and everything in-between. Locally offerings include walking trails/ restaurants, and family farms. We are located between Washington D.C. and Baltimore. Only a short 45 minute drive to D.C., you can spend the day exploring the museums and sites that the Nations Capital has to offer. Baltimore is 25 minutes away. A great place to see the National Aquarium. You will love your relaxing stay here in this rural area

Top guest favorite
A charming gray house is situated beside a manicured lawn, featuring a well-maintained driveway and an adjacent garage. Green shrubs and small trees are positioned around the property, creating a welcoming environment. A clear blue sky with fluffy clouds is visible overhead.
Home in Stevensville
4.91 out of 5 average rating, 101 reviews

Cheerful & Spacious Shore Life Beauty!

Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.

Guest favorite
Two adirondack chairs in blue and teal are positioned on a wooden pier, facing the sunset over calm waters. A small white table sits between them, holding two coffee mugs. The vibrant orange and pink hues of the sky reflect on the water's surface.
Home in Edgewater
4.98 out of 5 average rating, 172 reviews

Waterfront Chesapeake Bay Sunrises & Fishing Pier!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Guest favorite
An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.
Home in Riviera Beach
4.95 out of 5 average rating, 166 reviews

Waterfront Cheerful 5 home

Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 4 Bathroom .one bedroom on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

Guest favorite
The entrance of the guest cottage is framed by a charming picket fence, featuring a blue door and a welcoming porch. A small table with two chairs and an umbrella is situated on a wooden deck, surrounded by lush greenery.
Guesthouse in Annapolis
4.9 out of 5 average rating, 329 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Guest favorite
The entrance features double glass doors framed by a wooden deck. Seasonal potted plants, including vibrant flowers and greenery, are arranged on either side, while a small pumpkin adds a festive touch. A decorative light fixture hangs nearby, enhancing the welcoming appearance.
Cottage in Glen Burnie
4.91 out of 5 average rating, 223 reviews

Home away from home

This is a small house with private parking close to Baltimore and Annapolis. I have one queen size Murphy bed, one single pull out couch. It has an updated kitchen, updated bathroom, walk-in closet, Internet and heating and cooling. I also have a pellet stove. my kitchen is fully stocked with dishes, knives, forks, pots and pans. The bathroom has towels and rugs. I tried to add all the amenities to make it as comfortable as home. Look at pet rules under the other things to note section.

Top guest favorite
A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.
Cottage in Pasadena
4.97 out of 5 average rating, 187 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Guest favorite
The image illustrates a charming tiny home nestled among trees, featuring a spacious bluestone patio with outdoor seating and a fire pit. In the background, a gas grill is positioned nearby. Lush green grass surrounds the area, creating a serene and inviting setting.
Guesthouse in Annapolis
4.95 out of 5 average rating, 198 reviews

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Top guest favorite
A serene riverfront scene features a reflecting water surface, with the sky painted in soft pinks and purples at sunset. Lush greenery borders the water's edge, and silhouettes of trees frame the tranquil landscape.
Guest suite in Pasadena
4.98 out of 5 average rating, 658 reviews

Sea Dreamer

Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Guest favorite
A serene waterfront scene showcases a small boat gently resting on the shore, surrounded by lush greenery. A wooden dock extends over calm waters, where kayaks and paddle boards are visible nearby. The setting invites relaxation and engagement with the natural surroundings.
Home in Riviera Beach
4.79 out of 5 average rating, 105 reviews

Beautiful Baycation Stay

This Baycation stay is perfect for friends and family looking for a waterfront stay just 25 minutes from BWI Airport, Downtown Baltimore and Downtown Annapolis. Offering amenities like kayaks, crabbing, paddle boards, firepit, WiFi with all streaming services and toiletries to make sure you have everything in case you forget. There is a home office space set up! Kitchen stocked for home cooking, relaxing, and a guest book for eating out.

Guest favorite
A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.
Place to stay in Glen Burnie
4.93 out of 5 average rating, 381 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Popular amenities for Pasadena vacation rentals

When is the best time to visit Pasadena?

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Avg. priceG$26,640 GYDG$26,016 GYDG$32,468 GYDG$33,092 GYDG$34,965 GYDG$34,965 GYDG$33,300 GYDG$33,092 GYDG$28,930 GYDG$34,965 GYDG$32,468 GYDG$37,671 GYD
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Pasadena?

    Four-legged friends are welcome in Pasadena. Choose from more than 30 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 50 vacation rentals in Pasadena featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Pasadena?

    Make yourself at home in Pasadena by choosing from our most frequently booked neighborhoods. We have over 190 vacation rentals in Green Haven, and over 40 vacation rentals in Sunset Beach.

  • Are there Pasadena vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Pasadena, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly house rentals in Pasadena?

    Pasadena has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Pasadena with our townhouse rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Pasadena have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Pasadena. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Pasadena have wifi?

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

Quick stats about vacation rentals in Pasadena

  • Total vacation rentals

    Explore 70 vacation rentals in Pasadena

  • Nightly prices starting at

    Pasadena vacation rentals start at G$6,244 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Pasadena vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Pasadena rentals

  • 4.8 Average rating

    Pasadena stays are highly rated by guests—averaging 4.8 out of 5!

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