Vacation rentals with a pool in Cambridge

5 out of 5 average rating, 156 reviews

A charming guesthouse is depicted, featuring a light-colored exterior with multiple windows and a red accent staircase leading to the upper floor. Cozy seating is provided on the porch, surrounded by greenery and set beside a covered area with a clock and decorative elements.

Guesthouse in Annapolis

Private Art-Filled Guesthouse near Naval Academy

CameronRating, 5 stars3 months ago

Came in from North Carolina for first time in Annapolis and was a great location to the Navy football stadium. Walking distance to great food and local stores. Linda has a great place and was very nice to chat with coming and going from the property. 10/10 stay!

4.87 out of 5 average rating, 132 reviews

Guest suite in Arnold

Cozy Comfort - only 7.5 Miles to Annapolis & USNA

DeborahRating, 5 stars2 weeks ago

A cozy and very clean retreat! I was so impressed with how comfortable and welcoming this place was. There are plenty of windows and sliding glass doors which offered sunlight by just opening the blinds and curtains. Temperature was perfect inside. A fan and heater were provided in each bedroom if extra coverage was needed. We only stayed one night to attend a local music event but wished we had booked the whole weekend! We will be back!

Apartment in Stevensville

A spacious backyard features a large in-ground pool surrounded by landscaped gardens. Comfortable seating areas with shaded pergolas are positioned nearby, offering a perfect spot for relaxation. The house stands in the background, complementing the serene outdoor environment.

4.98 out of 5 average rating, 273 reviews

Boutique by the Bay

MicheleRating, 5 stars5 months ago

Enjoyed our stay and appreciated all of the details like creamer in the refrigerator this morning. Tastefully appointed and very comfortable - exactly as pictured. We were in the area for a wedding and Diane was flexible and communicated throughout the reservation/stay. We would love to go back and stay longer.

4.96 out of 5 average rating, 174 reviews

A well-maintained inground pool can be seen surrounded by a spacious deck featuring lounge chairs and shaded seating areas. Lush greenery and trees create a natural backdrop, enhancing the outdoor space’s tranquility with direct views of the water.

Apartment in Arnold

Celebrate Summer by Your Private Pool

JennaRating, 5 stars7 months ago

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

Cottage in Saint Michaels

4.98 out of 5 average rating, 160 reviews

La Casita on Harris Creek, St. Michaels

NinaRating, 5 stars4 months ago

Mike and Melinda’s place was a quiet, beautiful retreat surrounded by nature and exactly what we were looking for! We even got a visit from a bald eagle! The space was thoroughly appointed (as listed) and the attention to detail was impressive. The welcome basket was filled with local goodies and we very much appreciated the thorough written instructions and recommendations for local activities and restaurants. Although the cottage was close to the main house its orientation makes it very private. Winter weather cooperated and we even enjoyed a private romantic firepit! Everything was included of course - even the s’more kit. Would definitely stay again and couldn’t ask for better hosts!

4.99 out of 5 average rating, 206 reviews

A serene outdoor area features a saltwater swimming pool surrounded by comfortable seating, including wicker chairs and side tables. Lush greenery frames the space, with a view of the water beyond. Lanterns are placed around the pool for added ambiance.

Home in Tracys Landing

The Little Gypsy BoHome

ToddRating, 5 stars2 weeks ago

The place was perfect, clean, homey, comfortable and really unique. Loved the pool, cold plunge, sauna, screen porch. We had everything we needed from fresh flowers and cookies to convenient multiple charging stations by the beds. Loved the outdoor lighting and overall coziness of this place. Quiet and peaceful, sounds of the water lapping the shore, beautiful place to drink morning coffee and watch the sunrise. Also found some great sea glass on the beach!! Love, love, loved staying here :)

A serene pool area is framed by lush planters and a wooden railing. Comfortable lounge chairs are arranged around the pool, with several umbrellas providing shade. Sailboats are anchored in the marina beyond, under a clear sky illuminated by the setting sun.

4.96 out of 5 average rating, 272 reviews

Annapolis Waterfront Condo - Unit #: A-203

CarolineRating, 5 stars1 week ago

The condo was great, and I felt right at home as soon as I walked in the door. I was very tired after a day of sightseeing, and the combination of a very comfortable bed and a quiet neighborhood made for a good night of sleep. The location is walkable to all of the sights in Annapolis. Jane is one of the best hosts that I have stayed with. She messaged me with very clear instructions to get into the unit, and checked in from time to time to make sure that I had everything I needed. I would love to stay with her again.

Guesthouse in Stevensville

4.99 out of 5 average rating, 267 reviews

Waterfront Getaway - View of bay from your bed

OlgaRating, 5 stars2 weeks ago

Our stay was peaceful, beautiful, and full of thoughtful details. We loved the privacy—hosts were respectful, responsive, and never intrusive. The view is exactly as in the photos: calm, endless, and grounding. It truly felt like a quiet European escape. Aesthetic touches everywhere made it feel intentional and comforting. The space is cozy, so for longer stays with lots of luggage, keep that in mind. There's extra storage below, though it may not be convenient for everyone. Inside: great shower, lovely tub, coffee, tea, and the best complimentary coffee we’ve had in ages—don’t skip it. We enjoyed every sip by the water. Pet-friendly, tasteful, quiet, and designed with care. Annapolis also surprised us with excellent seafood, fresh oysters, and a warm coastal vibe. Our stay was short, but full of beauty, quiet joy, and a sense of pause. A perfect little retreat to reset and breathe.

4.95 out of 5 average rating, 136 reviews

Home in Harwood

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

JessicaRating, 5 stars1 month ago

Liz has a special place to make memories at. It's beautiful inside and out, spacious and well appointed. We were able to enjoy the outdoor areas, walk on the paths and venture out to the near by waterfront restaurants. A very large space that feels super cozy. Liz was great and super helpful along the way. We would 100% rebook.

5 out of 5 average rating, 102 reviews

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage in Easton

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

AcaciaRating, 5 stars3 days ago

Cheryl’s stay was so peaceful, comfortable and fun — even before pool season started. We could not believe how large the yard was and how quiet it was. Amazing wildlife. We saw bald eagles, heron, geese and lots of ducks! The house was squeaky clean and had everything we needed. We watched the stars at night and slept soundly. Downtown St. Michael’s is only about 10 minutes away and full of fun things to do. We’re so happy to be acquainted with the area after staying at Cheryl’s!

4.99 out of 5 average rating, 108 reviews

An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.

Cabin in Saint Michaels

True St. Michaels 6 Acre Waterfront w/heated pool

KyleRating, 5 stars3 months ago

Marissa’s home was beautiful and had everything we needed - plus some. Plenty of clean/comfort space and restrooms for our party of 6. We had such a relaxing, warm stay during a snowy January weekend - even smores! Marissa was always responsive and provided suggestions for shopping and dining in St. Michael’s. It was lovely all the way around! Highly recommend this home and working with these owners. Top notch!

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Popular amenities for Cambridge rentals with a pool

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Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 52 reviews

Home in Magnolia

Spacious 5 Bedroom w/Pool, Patio and Theater

StephanieRating, 5 stars3 weeks ago

This is our second time staying at Kristy's place. Just like last time, it was a beautiful home in a quiet neighborhood. Very comfortable! Every time I've communicated with Kristy she's been quick to respond and very helpful. Highly recommend!

4.69 out of 5 average rating, 13 reviews

A modern home is featured with a spacious pool area, showcasing a large blue pool surrounded by lounge chairs. A red umbrella provides shade on the deck, while the home's large windows offer views of the surrounding greenery.

Home in Arnold

Mins to Annapolis from Waterfront home Pool, Pier

VickyRating, 5 stars10 months ago

House owners were extremely responsive and informative. House was well stocked , and a great location and view made the stay even better.

4.81 out of 5 average rating, 156 reviews

A refreshing saltwater pool is framed by comfortable lounge chairs in vibrant red and blue. A large grassy area is visible beyond the pool, leading to serene waterfront views under a clear blue sky, complemented by a tree providing shade.

Home in Queenstown

Bay Breeze Retreat

EeshaniRating, 5 stars7 months ago

Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.

4.96 out of 5 average rating, 112 reviews

The exterior view showcases a spacious backyard with an inviting swimming pool surrounded by lounge chairs and blue umbrellas. A two-story gray house stands prominently, with a deck and seating area visible, all framed by greenery and a clear sky.

Home in Cambridge

Gorgeous, waterfront home. Perfect for Families.

Leslie RogersRating, 5 stars4 months ago

We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!

4.94 out of 5 average rating, 16 reviews

Home in Deale

Modern Bay Dream

Olani Rating, 5 stars2 months ago

Rick was very supportive and his communication was superb. Great host with a beautiful cozy home. 5 star all across the board.

5 out of 5 average rating, 52 reviews

A two-story home is presented with a brick facade and light-colored siding. Green shutters frame the windows, while a small garden with shrubs and flowers is located at the front. A driveway leads up to the entrance steps, surrounded by well-maintained lawn and trees.

Home in Salisbury

Loch Raven Retreat/spacious home w/ private pool

ElizabethRating, 5 stars2 weeks ago

The cleanest AirBnB we’ve ever stayed in! Great location, easy communication with the host. Would not hesitate to book Loch Raven again.

5 out of 5 average rating, 29 reviews

A spacious outdoor area features a rectangular pool surrounded by a paved deck. Lounge chairs and tables are arranged around the pool, with a covered seating area visible in the background. A hot tub is positioned nearby, enhancing outdoor leisure options.

Home in Stevensville

Wildbluesea Retreat

TerriRating, 5 stars6 months ago

We came to the area for a wedding and had 8 adults and 2 children. There was plenty of room and everything was very clean and welcoming. There was a large table for all of us to fit at and eat together and we especially enjoyed our time in the hot tub. Janean was very quick to respond and gave us great recommendations for dinner. The area was beautiful and we would definitely love to come back some time in the future and stay at the Wildbluesea Retreat!

5 out of 5 average rating, 138 reviews

A serene poolside area is framed by lush greenery and a large tree, providing a peaceful view of the water. Lounge chairs are positioned for relaxation, with picnic tables nearby. The clear blue sky and calm water create a tranquil atmosphere.

Home in Lusby

Historic Rousby Hall, Waterfront, Patuxent River

ShannonRating, 5 stars3 months ago

What a lovely stay! Incredibly charming home with such hospitable hosts. Our group felt comfortable and relaxed. Picturesque environment.

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Condo rentals with a pool

Condo in Cambridge

4.88 out of 5 average rating, 8 reviews

A Kozy Waterfront Condo

MicheleRating, 5 stars5 months ago

The photos are mirror images of the condo. The kitchen and bath are amply supplied with all the items needed, even to prepare meals if you choose. Accessibility features are a bonus when traveling with an individual with mobility issues. Locally, Portside Seafood was a welcome surprise with a delicious menu. It was the perfect place for my sister and me to have some downtime and recharge. Thank you for sharing your beautiful home.

A spacious living area features comfortable leather seating, a large smart TV, and artistic wall decor. An anchor-themed throw pillow adds character, while natural light flows in through the expansive windows, highlighting the warm hardwood floors and cozy atmosphere.

4.57 out of 5 average rating, 7 reviews

1BR water-view condo with rooftop pool & balcony

BennettRating, 5 stars2 weeks ago

First and foremost, Vacasa were extremely responsive to an issue that arose. The moment that I notified them of a problem with the unit (which wasn’t really their fault, nor ours), they moved quickly to resolve the issue. A+ there. Apart from that, the unit was great. Very clean, tastefully appointed and decorated. Only a 15 min walk to downtown, but there are other great restaurants even closer. Only negatives were minor: the view of the water was non-existent from inside the unit; the platform bed in the main BR may be too high for anyone with mobility issues (bring a stool); the other beds (a fold-out couch and a Murphy bed) don’t really offer any privacy; and the pool (that is literally in the title description) was inaccessible. I realize it’s not really pool season yet, but it WAS warm enough to swim when we visited, and my young daughter was looking forward to it. I just would’ve appreciated a heads-up in the ad that the pool was actually closed.

The kitchen features aqua and white cabinetry, complemented by a spacious granite countertop that houses four high-backed chairs. Stainless steel appliances are visible, with a window allowing natural light to enhance the warm tones of the space.

4.77 out of 5 average rating, 81 reviews

Amazing Views from Spa Creek 2BD Condo with Pool

ShellyRating, 5 stars3 months ago

Loved our stay at Marie’s condo. The place was clean, well-stocked and cute. Comfortable beds. Unbelievable view of the water and State House. A 10!

A comfortable living area is displayed, featuring a sectional sofa and a coffee table on a textured rug. A wall-mounted television is visible, alongside a stylish fireplace. The open layout connects to the kitchen area, with warm lighting illuminating the space.

4.99 out of 5 average rating, 73 reviews

Charming Annapolis Waterfront Condo

AnnaRating, 5 stars1 week ago

We really enjoyed our stay! The place was clean, comfy, and had everything we needed. Jared was super responsive and helpful. I highly recommend.

An aerial view reveals the marina along Spa Creek, showcasing numerous boats and yachts docked in calm waters. The charming waterfront area features picturesque buildings and green spaces, with the nearby drawbridge visible in the distance.

4.2 out of 5 average rating, 10 reviews

Upscale Waterfront Condo Annapolis

LaurieRating, 5 stars36 months ago

What a beautiful setting! As the others have said, it's in the perfect location with a beautiful view of St. Mary's church and the Maryland statehouse dome. Freshly renovated, you'll find a fully-tiled shower in place of the usual tub/shower combo. This is a perfect place for someone who does not like stairs. Easy access in and about the condo complex. The kitchen is fully equipped for anything you'd like to do, if cooking in. There are no curtains in the windows of the living space. There is a shade in the bedroom. The bed is comfortable, as are the sofa and loveseat. My husband and I stayed here for 6 months while our house was being renovated, and we felt quite at home.

An open living area is showcased, featuring a light-colored sofa against a wall adorned with framed photographs. A large rug anchors the space, complemented by a round dining table and chairs. Natural light floods in from large sliding doors leading to a balcony.

4.96 out of 5 average rating, 50 reviews

Cozy Annapolis Condo

JoeRating, 5 stars3 months ago

Host gave an accurate description. Also, gave clear and easy instructions for checking in to condo. Had everything we needed. Comfortable beds! Would highly recommend if you're visiting the Annapolis area.