Vacation rentals in Highland Beach

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Top-rated vacation rentals in Highland Beach

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Guest favorite

A leather couch with decorative cushions is positioned in a well-lit living area. A modern piece of artwork adorns the wall behind the couch, while potted plants add a touch of greenery. Bright natural light filters through two glass-paneled doors.

Apartment in Annapolis

4.92 out of 5 average rating, 488 reviews

Wall to Wall Cool- Filled with Original Art and Sculpture

This apartment is on one end of a larger main house. The shared wall was retro-fit with sound dampening cellulose fill in February of 2018. This enhancement along with many others provide the feel and comfort of being in your own space. This is Listed as 2 bedrooms, however there is no door between the 2 rooms. They are separated by 3 steps and a hallway. Please see pictures for a thorough view of the layout. Proximity to destinations; Vin 909 0.2 miles, Boatyard Bar & Grill 0.3, Eastport bridge, gateway to the downtown area 0.7 miles, City Dock 1.1 miles, Naval Academy 1.2 miles There is a Murphy Queen cabinet Bed, plus a Leather couch that turns into a queen bed allowing 4 to sleep comfortably, 2 to a bed. Very calm and relaxed space, a great place to recharge as you discover the area. Of Note: Hotel cleanliness standards vary greatly; with comforters frequently being a little dubious. Just how many turnovers are factored in before they get washed? High traffic carpeted floors can hide unwanted history. Walking in your bare feet should only make you feel free, never uneasy. Our pledge; every guest will sleep on clean sheets, over a freshly sanitized mattress cover under a bed comforter or bed blanket that was cleaned before their visit. When shams are present, they are laundered every single time. All surfaces are cleaned and if something’s not right, let us know and it will be. Life can be a mystery, but your Airbnb stay should never be. Shared Use of the Front porch to the right of the house. Wifi, (2) 4K TV's one 48" and the other is 60", industrial under counter fridge that will keep everything nice and cold. Dishes, glasses plates are all available. The (2 ) Roku TV remotes have inputs for standard ear buds, so you can stay up way late and watch TV while not waking up your friend/spouse/relative, buddy, just plug in... I'm kind of a non-intrusive, sort of do my own thing sort of person. Very mindful not to step on other peoples good times. Available through text to answer any questions you may have. I've lived in the area most of my adult life and am always happy to help. The house is in the eclectically odd neighborhood of Eastport. It's close to great restaurants, bars, and pubs. Vin 909 Winecafe is less than a five-minute walk from the house, and it's across the street from three more restaurants and a drug store. Walk it man, walk it! it's good for you and what's the rush. Driving downtown can be painful and crowded. Plus why pay the man to park, when you've got free parking at the house? Proximity to destinations; Vin 909 0.2 miles, Boatyard Bar & Grill 0.3, Eastport bridge, gateway to the downtown area 0.7 miles, City Dock 1.1 miles, Naval Academy 1.2 miles The house is on a main road to downtown. So there is a fair amount of traffic in front of the house. There is also a fire station just down the road, so passing sirens often accompany the din of general city traffic. For your comfort there is a white noise machine in the front bedroom area. There is also a small fan in the closet if you prefer to sleep with a fan. Please use caution when pulling out of the drive way. When walking downtown, the side streets are much quieter, so pick the path that best suits you.

Top guest favorite

The cottage is showcased amid a wooded setting, featuring a gravel parking area. A small covered porch is visible, accented by colorful chairs. Lush greenery surrounds the structure, and a glimpse of Mill Creek can be seen in the background.

Cottage in Annapolis

4.96 out of 5 average rating, 408 reviews

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 157 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Top guest favorite

A cozy seating area features two armchairs positioned around a low table, set on a patterned rug. A brick fireplace is the focal point, with a wooden mantel displaying decorative items. A flat-screen TV is mounted above, and a bookcase is visible to the side.

Guest suite in Arnold

4.96 out of 5 average rating, 671 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Guest favorite

A spacious backyard features a pool reflecting the soft glow of lights strung along the house's back deck, creating a serene evening ambiance. The two-story home is visible in the background, illuminated alongside the surrounding greenery.

Guest suite in Arnold

4.94 out of 5 average rating, 176 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.

Top guest favorite

An inviting living space features a comfortable sofa and a wall-mounted television. A modern kitchen area includes dark cabinetry and light furnishings, while large glass doors lead to a covered deck with scenic water views. Natural light enhances the airy atmosphere.

Houseboat in Kent Narrows

4.97 out of 5 average rating, 152 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Top guest favorite

Home in Shady Side

5 out of 5 average rating, 171 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

Guest favorite

A wooden sign displaying the name 'bean rush café' is mounted on a white fence. The café entrance is visible in the background, along with a flag displayed on the porch. Green foliage surrounds the sign, contributing to a welcoming neighborhood vibe.

Guesthouse in Annapolis

4.9 out of 5 average rating, 290 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Guest favorite

A coffee station is presented with a sleek coffee maker and two light blue mugs on a granite countertop. A bag of organic house roast coffee, labeled 'Rise Up,' adds a touch of warmth to this functional space.

Guesthouse in Annapolis

4.86 out of 5 average rating, 101 reviews

Chesapeake Bay Escape | Cozy Retreat

Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtfully interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

Top guest favorite

Guesthouse in Stevensville

4.99 out of 5 average rating, 279 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.

Superhost

A compact bathroom area is visible, featuring a pedestal sink beneath a wall mirror. A shower curtain with a decorative pattern hangs by the shower area. Light enters through a window, enhancing the neutral walls and tiled floor.

Apartment in Annapolis

4.77 out of 5 average rating, 265 reviews

Charming Eastport

Who needs a boat to stay at a marina? Eastport Yacht Center has a quaint one bedroom apartment located in charming Eastport, within walking distance to Downtown Annapolis and the U.S. Naval Academy. Conveniently located next to the Annapolis Maritime Museum. (Two guests maximum) If this apartment isn't available for your time period check out our other studio apartment listed under "NEW lovely studio apartment with onsite parking".

Top guest favorite

A bright kitchen is oriented towards waterfront views, featuring white cabinetry and a spacious island. Two bar stools are positioned at the island, while a seating area with a light-colored couch is visible. Natural light floods the space through sliding glass doors, enhancing the airy atmosphere.

Guesthouse in Annapolis

4.99 out of 5 average rating, 168 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

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Other great vacation rentals in Highland Beach

Guest favorite

The spacious living area features a ping pong table at its center. Comfortable seating, including a couch and bean bags, surrounds the space. Soft lighting from recessed fixtures creates an inviting ambiance, while a doorway leads to a bathroom, visible through an adjacent archway.

Home in Annapolis

4.94 out of 5 average rating, 65 reviews

Naptown Suite

LilianRating, 5 stars1 week ago

Enjoyed her place and look forward to staying here again.

Top guest favorite

The kitchen features modern appliances, including a stainless steel refrigerator and a spacious sink. Natural light enters through a window above the countertop, illuminating the granite surface. Decorative elements include a vase on the island and subtle lighting fixtures overhead.

Home in Shady Side

4.96 out of 5 average rating, 26 reviews

Ruby Of The Bay

StarlaRating, 5 stars2 weeks ago

Can’t say enough good things about our stay! Beautiful place with everything we could possibly need. The kitchen was well stocked and our host had thought of everything! Clear instructions, great recommendations for local spots etc. And the huge backyard and deck was perfect for us and our pups. Very comfortable beds and pillows too! Finally, host communicated so well and was incredibly accommodating.

Top guest favorite

The entrance features a welcoming front porch with a covered area. A white front door is flanked by large windows and decorative planters containing tall green plants. The porch is accessed by a set of steps leading to a wooden walkway.

Home in Annapolis

4.98 out of 5 average rating, 53 reviews

Annapolis Retreat - Near DTA with Tons of Parking!

AmiRating, 5 stars2 weeks ago

Ronny was a very communicative and gracious host. The home was beautiful and well stocked. It was in a private area with a short commute to plenty of restaurants and services. Would highly recommend for anyone staying in the area!

Superhost

A bright and spacious kitchen features modern cabinetry and a large window allowing natural light. Basic appliances are arranged along the walls, and a countertop provides ample space for meal preparation. Light wood flooring complements the clean, minimalist aesthetic.

Home in Edgewater

4.82 out of 5 average rating, 22 reviews

South River Beach Front House

Katherine Rating, 5 stars1 month ago

I stayed here the week of my wedding and it was absolutely perfect! From waking up each morning to have coffee on the dock with my pups and husband, to the beautiful views from each room in the house, we truly had a lovely time and chose the right Airbnb for such a special week in our lives.

Guest favorite

A screened-in porch features a sectional sofa perfectly arranged around a low coffee table, creating a comfortable space for relaxing. Natural light floods the area through multiple windows and a skylight, with a view of the yard visible beyond the porch.

Cottage in Annapolis

4.93 out of 5 average rating, 76 reviews

Peaceful Escape: Bay Ridge Cottage by the Bay

LindseyRating, 5 stars1 month ago

Our stay at Tiffany’s was just what we needed! A small cottage with just the right amount of room for our family, with a walkable neighborhood filled with charm and steps away from the bay! The screened in porch was heavily used for lunches and afternoon naps! Everything you could need for a family with small kids (mine were 4 and 19 months) was included too! While nothing in terms of food within walking distance, everything you needed was 5-10 mins driving and was not bad - good selection of restaurants too. Was very happy with location for a quiet secluded getaway, which now leaves me dreaming of a future retirement home in this area! Thanks for sharing your family home with us Tiffany!!

Top guest favorite

Guest suite in Annapolis

5 out of 5 average rating, 28 reviews

Pristine, Private 1 Bed/1 Bath Guest Apartment

DaniellaRating, 5 stars3 weeks ago

Fox Haven is heaven on earth. So quaint, so clean, so many thoughtful extras including a healthy snack basket, toiletry items, and personal touches throughout the apartment. The location is outstanding with a short walk to historic downtown Annapolis. Lenetta is one of the most responsive and personable Air B&B owners we've ever experienced. We will be back for sure! Highly recommend Fox Haven to everyone!

Guest favorite

A sunroom is shown with a large window providing views of the water. Two wicker chairs and a glass table occupy the space. A door with a dark finish is visible, and natural light enhances the serene atmosphere.

Cottage in Edgewater

4.92 out of 5 average rating, 51 reviews

Waterfront Cottage with Private Pier

StephanieRating, 5 stars1 week ago

Beautiful setting. Very cozy house that was well appointed with everything that we needed for a longer stay. I was able to cook full meals in the kitchen with ease and my husband grilled one night. Other than that, there are local restaurants to enjoy as well. During the day my boys had fun fishing and being out on the water and the sunsets over the lake was definitely worth sticking around for. Unfortunately I had to work during the majority of our stay but I was able to do that seamlessly with the desk and reliable internet connection. Overall we had a great time at Miss Kitty’s Place and would love to stay there again someday.

Top guest favorite