Vacation rentals with a pool in Annapolis

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Annapolis

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

Guesthouse in Annapolis

5 out of 5 average rating, 156 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

Apartment in Upper Marlboro

4.95 out of 5 average rating, 121 reviews

DC Oasis- hot tub, pool, theater/game rm, & more

Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, 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. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from Downtown DC & 6Flags.

Guest favorite

Guest suite in Arnold

4.87 out of 5 average rating, 132 reviews

Cozy Comfort - only 7.5 Miles to Annapolis & USNA

Close to historic Annapolis, our cozy first floor guest apartment of our home in a quiet large single family home neighborhood. 'The Oasis' is private and spacious with 2-bedrooms, a living room, mini sit-in kitchen, bathroom, and laundry room. Close to waterfront restaurants, B & A trail, Sandy Point Public Beach and Park, festivals, shopping, bowling, miniature golf, wineries and more. Our guests are welcome to enjoy some time relaxing in our wooded backyard with pool (unheated) and gazebo.

Top guest favorite

Apartment in Stevensville

4.98 out of 5 average rating, 273 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.

Guest favorite

Guest suite in Arnold

4.94 out of 5 average rating, 168 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Guest favorite

Home in Severn

4.88 out of 5 average rating, 161 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

Relax at this large 7-bedroom spacious top-quality home that is ideal for large gatherings where all can be together in one place. All will be comfortable in large open areas both inside (4,125 sq ft, tall ceilings) & outside (1 acre). Enjoy a huge first-class kitchen with all the granite countertop space, cooking & serving supplies you will ever need. Enjoy the large fenced-in backyard with pool, grill, & fire pit. Ideal for family events, quiet getaways, sports teams, & business meetings

Guest favorite

Apartment in Arnold

4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

Lovely 2 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 water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Top guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 206 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Top guest favorite

Condo in Annapolis

4.96 out of 5 average rating, 273 reviews

Annapolis Waterfront Condo - Unit #: A-203

BOOK NOW FOR SUMMER 2025! SPRING and FALL BOAT SHOW AVAILABILITY! Free reserved parking! Walk to show in minutes! Great views - 2nd flr. condo (12 stairs, no elevator.) Pool hours are fixed: Mon: 4pm-8 Tues: Closed Wed: 4-8 Thurs: 4-8 Fri: 3-8 Sat/Sun/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 location. 15 min. walk to downtown Annapolis/USNA. MULTIPLE Free parking options.

Top guest favorite

Guesthouse in Stevensville

4.99 out of 5 average rating, 268 reviews

Waterfront Getaway - 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.

Top guest favorite

Home in Harwood

4.95 out of 5 average rating, 136 reviews

Luxury Home, Sleeps 15, Private Pool, Close to DC

Stunning 6 bedroom, 5½ bath home on 34 acres with panoramic woodland views and private salt water pool, perfect for that special gathering. Secluded yet just 35 minutes from Capitol Hill and 20 minutes from Annapolis. The home, with its high ceilings, huge windows and expansive decks comprises over 8000 square feet, so there is plenty of room to stretch out. *** IMPORTANT Please send AN INQUIRY with a little about you PRIOR to requesting a booking.

Top guest favorite

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

0 of 0 items showing

What guests are saying

Stunning North Beach Getaway w/ Inground Pool

5 out of 5 average rating, 14 reviews8 months ago

Patti was an amazing host. She made sure that we had everything we need and she went the extra mile providing toys for our toddler. The house was beautiful. Very peaceful neighbourhood and you can just walk to the beach where you can find nice restaurants and a playground. Perfect getaway for families. And the heated pool is the icing on the cake

Home in North Beach

What guests are saying

The Little Wooded Casita

4.96 out of 5 average rating, 27 reviews2 weeks ago

These hosts are the best - kind, friendly without being intrusive, and always ready to help. The property is impeccably maintained and thoughtfully appointed - lovely decor, nice bed and cozy linens, and coffee, tea, and cooking supplies in the kitchen. We are retreat guests, and this was our first visit when the weather was nice enough to sit on the deck of the bedroom. Lovely! You will not regret a stay at the Little Wooded Casita.

Guesthouse in Silver Spring

What guests are saying

Newly Renovated Summer Paradise-Pool-Tennis-Garden

5 out of 5 average rating, 11 reviews1 month ago

Spent a few nights in the garden cottage with best friends from college. The property is amazing. It takes a while to get there but worth it! Mark, the caretaker, took us on a tour of the grounds when we arrived. We were able to check in a little early. Our cottage was nice, but it lacked a lot of the basics. Mark was great about immediately getting us what we needed. He even went out of his way and got us our own fire pit! We had a great time, saw amazing sunsets, went on long walks. St. Michaels is about 20 minutes away. Great little town to explore! All in all, it was a great place for us to get together!

Cottage in Royal Oak

What guests are saying

Entire Beach House with Pool and Hot Tub

4.98 out of 5 average rating, 53 reviews4 months ago

We had a great stay at this clean, comfortable, convenient and cozy house. We were impressed by the attention to detail. Every time we needed something, it was there. The kitchen was fully stocked and had everything we needed to cook our Thanksgiving meal. We were close to Annapolis And had an easy drive to the museums of DC. We took several walks to the nearby beach, and enjoyed both sunrises and sunsets. We would definitely come back! Thank you, Peggy!

Home in Edgewater

What guests are saying

Cozy cottage with riverview and pool

4.98 out of 5 average rating, 40 reviews1 month ago

My stay was very peaceful—I stayed for six weeks, and everything went perfectly. The house is exactly as described in the listing. The waterfront view brought me peace and tranquility, allowing me to focus on my work. Cindi is an amazing host; she was always available throughout my stay, making sure I felt at home. I highly recommend this cottage for both short- and long-term stays. It was the perfect choice for the transition period I was going through. Thank you, Cindi, for the wonderful stay!

Guest suite in Arnold

What guests are saying

Luxury Home with Pool for 20

5 out of 5 average rating, 15 reviews2 weeks ago

This was a great place for our family of 13 to stay during the weekend of our niece's wedding in Baltimore. The home has plenty of large common areas, dining space, and super comfortable beds - even the queen-size bunk beds on the lower level had high-end mattresses. The kitchen is well-equipped. We had 4 additional family members drop in for dinner on our last night there, and it was no problem preparing food for, and serving, 17 people. Everyone was happy with this choice for our accommodations.

Home in Severna Park

What guests are saying

Waterfront | Pool | Hot tub | Beach Access

4.98 out of 5 average rating, 64 reviews1 week ago

The moment we walked in we fell in love with this place. Clean newly appointed kitchen, open floor plan, fireplace, pool table, big TVs, children’s games, toys, and wonderful view of Big Pond. Great for bird watching. Beds were great, everything labelled and organized very smartly. Quick response to communications. We cooked a big meal and the kitchen was nicely stocked.

Home in Edgewater

What guests are saying

Waterfront Getaway

4.95 out of 5 average rating, 39 reviews5 months ago

Loved my stay at Calli’s place so much I extended twice! The surroundings are absolutely beautiful. I loved working remotely from the deck overlooking the water. Calli has kayaks right on the property’s beach, so getting onto the water is a breeze. If you’re lucky, Reef the lab will join you. 😉 Had the pleasure of meeting Calli’s father Dave, who lives on the property. Highly recommend!

Guesthouse in Queenstown

1 of 12 pages