Vacation rentals with a pool in Pasadena

Find and book unique homes with a pool on Airbnb

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 ﺩ.ﺇ 147 per night before taxes and fees

  • Verified guest reviews

    Over 380 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!

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 charming guesthouse exterior is showcased, featuring multiple entrances with glass doors. A staircase leads to the upper level. Two shaded seating areas adorned with potted plants and a clock are visible in a well-kept outdoor space, enhancing the inviting environment.
Guesthouse in Annapolis
5 out of 5 average rating, 171 reviews

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

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
4.86 out of 5 average rating, 219 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 guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in Saint Michaels
4.97 out of 5 average rating, 191 reviews

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

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
4.97 out of 5 average rating, 308 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
4.97 out of 5 average rating, 119 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.

Superhost
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
4.86 out of 5 average rating, 111 reviews

Secluded Tiny House With your own Private Pool

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

Top guest favorite
Condo in Annapolis
4.96 out of 5 average rating, 341 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, 570 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.

Guest favorite
Apartment in Arnold
4.96 out of 5 average rating, 189 reviews

Celebrate Summer In Your Private Pool & Hot Tub

Lovely two acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing waterfront home is conveniently located only eight miles from the Naval Academy and downtown Annapolis. WE DO NOT HOST PARTIES OR EVENTS. ONLY REGISTERED GUESTS ARE PERMITTED ON THE PROPERTY.

Guest favorite
Apartment in Upper Marlboro
4.94 out of 5 average rating, 205 reviews

Kone Oasis- hot tub, pool, theater/game rm.

Have fun and relax! Near every amenity. Huge Pool w/multiple cabanas, hot tub, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Now offering RV for additional cost to add additonal sleeping space. Basement apt so there is some movement noise. 20 mins to DC & National Harbor

Top guest favorite
Guest suite in Annapolis
4.95 out of 5 average rating, 134 reviews

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

Top guest favorite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville
4.99 out of 5 average rating, 352 reviews

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Popular amenities for Pasadena rentals with a pool