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Vacation rentals with a pool in Pasadena

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pasadena

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.
Home in Severn
4.88 out of 5 average rating, 201 reviews

Large Home with Private Pool, Gym, Sauna, 7 Bedroo

Relax at this spacious 4,125 sqft, top-quality home on 1 acre. This 7-bedroom, 2.5 bathroom home features a private pool, gym, sauna, and a massive family room with 10 ft ceilings, and a 67 " Smart TV. Enjoy the large 1st class chef's kitchen with all the cooking & serving supplies you will ever need. Enjoy the modern amenities, multiple workspaces, a wrap-around porch, a fire pit, & a grill. Ideal for family events, quiet getaways, sports teams, & business meetings. You are able to have your l

Top guest favorite
A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.
Apartment in Stevensville
4.98 out of 5 average rating, 296 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Top guest favorite
The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.
Home in Stevensville
4.96 out of 5 average rating, 111 reviews

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Guest favorite
A cozy sleeping area features a spacious bed with cotton bedding and decorative pillows. Natural light enters through a window, highlighting the minimalist design. An ottoman rests at the foot of the bed, with a bedside table and a storage unit visible in the space.
Tiny home in Glen Burnie
4.87 out of 5 average rating, 100 reviews

Private Tiny House -No Contact 24/7 Self Check-In

Secluded Tiny Guest House Retreat with Private Pool – Near Baltimore & Annapolis As you pull into the driveway, the city noise melts away—replaced by the serenity of trees and the inviting sparkle of your private in-ground swimming pool. This 320 sq. ft. Pool House is cozy. A large window fills the space with natural light to the ever-changing views of the wooded setting. Completely private stay – no shared spaces Self check-in with no contact Private pool exclusively yours during your stay

Guest favorite
A spacious living area is depicted with plush teal seating arranged around a coffee table. A modern entertainment unit is positioned against a wall, while large sliding doors open to a private balcony. Natural light enhances the warm tones of the decor.
Condo in Annapolis
4.97 out of 5 average rating, 118 reviews

1 bedroom -king in Annapolis- low cleaning fee

Brand New Vacation Rental – Prime Annapolis Location! 1 bedroom. Experience the best of Annapolis in this newly renovated, beautifully furnished 1-bedroom condo with a king bed and NO chore list! This open-concept retreat offers a bright, modern interior and a private balcony to unwind. Start your day with a scenic walk through Truxton Park trails or head to the boat ramp to catch a water taxi to downtown Annapolis! Whether you're here for relaxation or adventure, this is the perfect spot.

Top guest favorite
An outdoor hot tub features a sleek design with built-in jets, illuminated by soft purple lighting. The surrounding area is draped with white curtains, creating a secluded atmosphere. Seasonal use is indicated, adding a touch of relaxation to the outdoor space.
Place to stay in Annapolis
4.94 out of 5 average rating, 124 reviews

Chesapeake Bay View 3BR/2BA Duplex*HOT TUB*

“Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, outdoor 6-person hot tub, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. * Best Places To Stay Annapolis*Ice Skating

Top guest favorite
Condo in Annapolis
4.97 out of 5 average rating, 320 reviews

Annapolis Waterfront Condo - Unit #: A-203

Cozy, comfortable condo. Great views - 2nd flr. Fireplace 1 bed/bath condo, sleeps 4 max, covered, water front deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy stadium. Book NOW for the Summer! Easy access to Spring/Fall boatshows. 12 stairs, no elevator. Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another

Top guest favorite
A classic brick Colonial house is surrounded by well-maintained gardens and lush greenery. Large trees provide shade over the front lawn, which features manicured bushes and young saplings, contributing to the inviting exterior of the home.
Guest suite in Catonsville
4.94 out of 5 average rating, 557 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Top guest favorite
A wooden table is set with a bottle of Walnut Crest Cabernet Sauvignon and two etched wine glasses. A red apple rests in a dark, leather-like bowl, with a serene backdrop of green foliage visible through a screened window.
Guesthouse in Highland
4.98 out of 5 average rating, 303 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool (weather permitting) and adjacent walking trails.

Top guest favorite
The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.
Home in Perry Hall
4.99 out of 5 average rating, 128 reviews

Gunpowder Retreat

Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

Top guest favorite
Guest suite in Arnold
4.94 out of 5 average rating, 196 reviews

Cozy 1-Bedroom Retreat Near Annapolis, Sleeps 4

*New hot tub and pergola installed!* 💗 This updated suite is designed for comfort & convenience. Enjoy a king bed and a LoveSac sofa that converts into a queen bed, perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!

Top guest favorite
Guest suite in Annapolis
4.95 out of 5 average rating, 119 reviews

Annapolis Garden Suite

Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

Popular amenities for Pasadena rentals with a pool

Quick stats about vacation rentals with a pool in Pasadena

  • Total vacation rentals

    Explore 20 vacation rentals in Pasadena

  • Nightly prices starting at

    Pasadena vacation rentals start at R677 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 360 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Pasadena vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pasadena rentals

  • 4.9 Average rating

    Pasadena stays are highly rated by guests—averaging 4.9 out of 5!