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Holiday rentals with beach access in Saint Leonard

Find and book unique accommodation with beach access on Airbnb

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Popular amenities for Saint Leonard Accommodation with Beach Access

Apartment rentals with beach access

Guest favourite
Apartment in Annapolis
4.88 out of 5 average rating, 104 reviews

King George Downtown Annapolis Getaway

LindsayRating, 5 stars1 month ago
A great airbnb! Location couldn't be better - and the unit was clean, and well appointed. We would for sure rent from Julie again!
Top Guest favourite
Apartment in Stevensville
5 out of 5 average rating, 48 reviews

Heron Roost

EmilyRating, 5 stars1 week ago
This was unanimously our family's favorite AirBnB! Dana and Mike are the dream hosts! Our accommodations prior to our scheduled arrival were cancelled last minute and they immediately jumped in to help. They were extremely considerate of our privacy whilst being right next door but also quick to respond when we reached out to them. We could not of asked for a better mini-vacay in the middle of our travels. The beautiful surroundings, welcoming accommodations and hosts, attention to detail throughout amenities and decor, and impeccable cleanliness were top-notch. We really enjoyed the heated pool too. The kitchen and grill were easy to navigate and stocked with all essential items needed to prepare meals. The Monocle Meat Company and Lovepoint Deli & Wine are great local shopping options. If cooking is not in your plans, Avanti has amazing pizza. Thank you Dana and Mike for going above and beyond to make us feel at home! Heron Roost is now our must stay place when visiting MD.
Superhost
Apartment in Cambridge
4.9 out of 5 average rating, 130 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

JoanRating, 5 stars1 week ago
We rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.
Top Guest favourite
Apartment in Lexington Park
4.97 out of 5 average rating, 568 reviews

Historic St. Mary's City, MD

AnnaRating, 5 stars1 week ago
Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.
Top Guest favourite
Apartment in Colonial Beach
4.92 out of 5 average rating, 53 reviews

Sail Away To - Beachfront Views & Private Balcony

PadmanabhamRating, 5 stars3 weeks ago
Great place with fantastic views of the Potomac . Close to many dining options within walking distance. We went for a Memorial Day weekend and had a great time. I highly recommend.
Guest favourite
Apartment in North Beach
4.96 out of 5 average rating, 131 reviews

Bayside Oasis of Southern Maryland

PaulRating, 5 stars3 weeks ago
Sherril’s Bayside Oasis is an absolutely beautiful studio apt!!! It was spotless, comfy, and uniquely decorated. The location is convenient to the beach and within walking distance to plenty of shops and great restaurants and bars. Everything was smooth from check-in to departure. We had a wonderful stay and will most definitely check the availability of this rental when we visit North Beach again.
Top Guest favourite
Apartment in Annapolis
4.97 out of 5 average rating, 29 reviews

Bayside Retreat

AllieRating, 5 stars2 days ago
We had a great stay at Kathleen's listing. The apartment is in a great location, only 15 minute drive max to all of the nearby attractions. We enjoyed having some tranquility being away from downtown after a long day and the free parking! Kathleen stocked the place with all necessities and more - including snacks and recommendations. The neighborhood is beautiful to walk around, with views of the water everywhere! Definitely would recommend staying here!
Superhost
Apartment in North Beach
4.88 out of 5 average rating, 81 reviews

Spacious Beach House Top Floors - Walk Everywhere!

KendriaRating, 5 stars1 week ago
it's exactly what the photos show. the stairs for the loft was a little steep but it was very comfortable and enough room for my family.

Holiday House Rentals with beach access

Guest favourite
Home in Hague
4.97 out of 5 average rating, 162 reviews

Osprey's roost: Spring and summer 2025

DavidRating, 5 stars4 days ago
Very roomy for a family vacation. Great location and covered porch was great for taking in views of river and enjoying summer breeze. Host was responsive and provided detailed instructions.
Guest favourite
Home in Montross
4.98 out of 5 average rating, 106 reviews

Waterfront Retreat| Kayak+Beaches+Pool | Gameroom

DavidRating, 5 stars2 weeks ago
What a find! We were attending a wedding on the Potomac and found this gem of a place basically right next door. A perfectly appointed home in a peaceful, tranquil, beautiful setting. Connie was great! Responsive to our need to find the iron, not exactly an emergency, Connie responded immediately with it's location. Loved it!
Superhost
Home in Montross
4.92 out of 5 average rating, 208 reviews

The Glebe

KristinaRating, 5 stars2 weeks ago
We had such a wonderful stay! The house was beautiful, peaceful, and had everything we needed for a relaxing getaway. The layout was perfect for spending quality time together while still giving everyone space to unwind. Private beach access made it even more special—we made great memories, met some lovely neighbors, and even had a chance to paddle board and spot a stingray! Huge shout-out to Leigh, our amazing host—so thoughtful, responsive, and kind. We’re so grateful for the experience and would absolutely stay here again. Highly recommend!
Top Guest favourite
Home in North Beach
5 out of 5 average rating, 142 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

StephanieRating, 5 stars5 days ago
This was our second time staying at Kimberly’s home, and it was just as magical as we remembered. The views of the water are absolutely stunning—whether you’re enjoying your morning coffee or winding down in the evening, it’s hard to look away. The location is perfect: peaceful but just a short walk to shops and restaurants. We also really appreciated the Peloton and treadmill—such a bonus for staying active during our trip. Everything was spotless and thoughtfully prepared. Honestly, we didn’t want to leave. Already looking forward to our next visit!
Top Guest favourite
Home in Grasonville
4.95 out of 5 average rating, 272 reviews

River Front, Private Single Family Home

HeatherRating, 5 stars1 day ago
the stay was wonderful. A very relaxing and peaceful place. Easy to locate and get into. reasurants and grocery stores are near by
Top Guest favourite
Home in Shady Side
5 out of 5 average rating, 170 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

MelindaRating, 5 stars3 days ago
The venue, property and service made great memories. Our host went above and beyond to help and especially with a special request that only an exceptional person would do. We had a wonderful stay and look forward to another visit.
Superhost
Home in Scotland
4.9 out of 5 average rating, 133 reviews

Spacious Gorgeous Waterfront Home with Sunset View

AlisonRating, 5 stars1 week ago
This home is just as advertised...it is very large, great for several families vacationing together! Our group was small so we didn't even make use of all of the space. The house is right on Tanner Creek which is just beautiful for sitting on the dock and relaxing, paddleboarding and kayaking, birdwatching, etc. It's also about a mile from Lookout Point State Park which is absolutely gorgeous. Restaurants and grocery stores are few and far between in this area, so it's a good idea to bring your own food, and the kitchen is well stocked with pots and pans for cooking. If you are looking for a place to relax in a calm and beautiful setting, this is it!
Guest favourite
Home in Montross
4.99 out of 5 average rating, 155 reviews

Beach Please! River cottage w/private beach & dock

SarahRating, 5 stars2 weeks ago
My family and I stayed here for a week for our family vacation. We are a group of 8 (6 adults and 2 kids) and there was plenty of room for all of us. We barely left the house because with the beautiful view, dock, beach area, canoe, kayaks, hot tub, game room/ library, corn hole, and fire pit we all had plenty to keep us entertained. Everyone loved Mary & Shelly’s place, and it provided the perfect space for us to enjoy the river and each other’s company!

Holiday condos with beach access

Private room in Annapolis
4.68 out of 5 average rating, 158 reviews

La posada de Jorge

SeanRating, 5 stars3 months ago
Jorge has a great spot for you and is one of the nicest people you will ever meet … 100% recommend!!
Condo in Colonial Beach
4.29 out of 5 average rating, 7 reviews

Riverside Bliss: 2BR Downtown Haven

KirstenRating, 5 stars11 months ago
This place worked wonders for our family vacation. the place is very new and updated with 2 full bathrooms that were clean and spacious for beach time and baths with kids. colonial beach is a hidden gem in a historic little town that seems as though at one point was hustling and bustling but isn't quite as popular as it once was but trying to come back. if your a family looking for a uncrowded beach and some activities to do in the area then this place is great! we actually read about this place being in the heart of historic downtown. only thing we would have loved to see with this place is some outdoor patio spot at the home directly to be able to sit outside together. the location does not really have any night life during the week, not even on 4th of July. we went out at 9 pm and the bar closed at 10 pm which seemed way too early for a Thursday and holiday and being on the beach.
Condo in Colonial Beach
4.75 out of 5 average rating, 8 reviews

Charming Coastal Getaway In Downtown!

TimRating, 5 stars9 months ago
After a little miscommunication on the arrival time, everything was at it should be or better. Great location, clean, responsive well worth it. Great experience and will be back regularly.
Condo in Cambridge
4.81 out of 5 average rating, 16 reviews

The Station House: Upscale Condo in Cambridge, MD

MahiberyRating, 5 stars1 month ago
I had an amazing stay at Jen’s apartment! The space was exactly as described—clean, stylish, and super comfortable. The bed was cozy, the kitchen had everything we needed, and the little touches (like the kid’s Conner and lots of board games ) really made a difference. The location was perfect—close to everything but still peaceful at night. Communication with the host was smooth and fast, and they were incredibly helpful with local tips. I’d absolutely stay here again and highly recommend it to anyone visiting beautiful Cambridge!
Guest favourite
Condo in Cambridge
5 out of 5 average rating, 13 reviews

The Drinking Gourd: Stunning Cambridge Penthouse

MelanieRating, 5 stars1 month ago
We had a great stay at Jen's place! It was very spacious and comfortable, and walkable to downtown Cambridge which had plenty of restaurants and bars to explore. The beds were comfortable and the amenities were as described. Jen was a very responsive host and helped out with all our questions. She also offered lots of local recommendations in Cambridge and the surrounding area. I'd definitely recommend Jen's place if you find yourself in Cambridge, MD :)
Guest favourite
Condo in Colonial Beach
4.96 out of 5 average rating, 50 reviews

Rooftop bay and river views

TiffanyRating, 5 stars1 week ago
Brandon’s home was as beautiful as the pictures. We loved how easy it was to walk to everything in the town. The pool and rooftop patio were an added bonus. We enjoyed cooking in the large kitchen, and the house easily accommodated our group of 8. We will be back!
Guest favourite
Condo in Oxford
4.98 out of 5 average rating, 129 reviews

Cozy Oxford Getaway

StephanieRating, 5 stars2 days ago
Chris was a great host making check in and out so easy and flexible! The location of the place was perfect for walking to the market and to get coffee! The space was exactly like the pictures and perfect for a quick getaway with my fiance! Recommend this place!
Guest favourite
Condo in North Beach
4.96 out of 5 average rating, 26 reviews

Unbelievable beach views for 6

JuliannRating, 5 stars2 weeks ago
Condo was in a perfect location in North Beach area. Loved walking boardwalk and walked 5+ miles daily. Felt very safe in the area, everyone was so friendly. Mexican restaurant and Baia were fantastic. Very peaceful. Condo definitely worth the money. Host was very responsive and let us check in early and was quick to reply to any text questions. Loved the view!

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