Condo Rentals in Highland Beach
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Search Condos Rentals in Highland Beach from CA $282

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Our top choices for Highland Beach condo rentals

A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

A covered outdoor seating area with wicker furniture and potted plants.

A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

A modern living room with a grey sofa, a tufted armchair, and a coffee table. There is a dining area with a white table and chairs, and a kitchen in the background.

1. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking

Historic District

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."

Scott P.

The price is CA $320

CA $320

CA $759 total

includes taxes & fees

Nov 30 - Dec 1

Upscale Condo in Annapolis w/Private Parking

A living room with a dining table, two sofas, a coffee table, and a patterned rug.

A kitchen with white cabinetry, stainless steel appliances, and a 'FREEDOM RING' sign.

A bedroom with a bed, bedside tables, a dresser, a window, and a chair.

A two-story residential building with a garage, a front door, and a small front yard.

2. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy

Historic District

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very cute home in great proximity to naval academy"

JENNIFER E.

The price is CA $282

CA $282

CA $760 total

includes taxes & fees

Nov 8 - Nov 9

Chapel Gate 3BR Steps to City Dock & Naval Academy

A living room with a fireplace, a television mounted above it displaying an airplane, and a glass coffee table.

A wooden dock with two Adirondack chairs, a sailboat docked at a marina with other boats in the background.

A modern kitchen with white cabinets, a wooden island with bar stools, and a dining table with chairs.

A rooftop terrace with a brick building, a metal staircase, and outdoor seating.

3. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Eastport

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Excellent place to stay!"

Michaell M.

The price is CA $399

CA $399

CA $920 total

includes taxes & fees

Nov 10 - Nov 11

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

View all properties

Top reviews in Highland Beach

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

DoubleTree by Hilton Hotel Annapolis

Annapolis

10/10 Excellent

Bon emplacement et aux standards des Doubletree

Jean

Reviewed October 25, 2026Reviewed October 25, 2026

DoubleTree by Hilton Hotel Annapolis

A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

A modern lobby with a sectional sofa, a coffee table, and a blue armchair.

A hotel lobby with a bar area, seating arrangements, and a patterned carpet.

A modern living room with a fireplace, two armchairs, a coffee table, and decorative items.

Crowne Plaza Annapolis by IHG

Annapolis

10/10 Excellent

Nice for family

Tarun

Reviewed September 3, 2024Reviewed September 3, 2024

Crowne Plaza Annapolis by IHG

A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

A gym with treadmills, weight machines, and dumbbells.

Sonesta ES Suites Annapolis

Edgewater

10/10 Excellent

Clean. Very nice. Courteous staff.

karen

Reviewed November 11, 2025Reviewed November 11, 2025

Sonesta ES Suites Annapolis

A circular fire pit surrounded by outdoor seating with a brick wall and a multi-story building in the background.

A compact hotel room with a kitchenette, a desk with two chairs, a sofa, and a bed.

A modern kitchen with a white countertop, stainless steel appliances, and wooden cabinets.

A hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.

TownePlace Suites by Marriott Annapolis

Annapolis

10/10 Excellent

All good great room suite all high end Staff eere the best i have experienced in a longtime

Steven

Reviewed April 18, 2026Reviewed April 18, 2026

TownePlace Suites by Marriott Annapolis

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

Courtyard by Marriott Annapolis

Annapolis

10/10 Excellent

Okay

Shirley

Reviewed July 16, 2026Reviewed July 16, 2026

Courtyard by Marriott Annapolis

A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

Graduate by Hilton Annapolis

Annapolis

10/10 Excellent

Great burger in restaurant

JONATHAN

Reviewed September 15, 2026Reviewed September 15, 2026

Graduate by Hilton Annapolis

A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

A historic brick building with a red roof, multiple windows, and a central staircase.

Historic Inns of Annapolis

Historic District

10/10 Excellent

Great hotel great location. Friendly staff

Kelly

Reviewed April 29, 2026Reviewed April 29, 2026

Historic Inns of Annapolis

A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.

A hotel room with a bed, bedside tables, a desk with a chair, a microwave, a refrigerator, and a window with curtains.

A modern hotel lobby with a sofa area, a flat-screen TV, and a dining area.

A reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Gambrills

10/10 Excellent

Super clean

Mario

Reviewed May 12, 2026Reviewed May 12, 2026

Microtel Inn & Suites by Wyndham Gambrills/Odenton

A hotel room with two beds, a desk with a chair, a television, and a large window with a view of greenery.

Hilton Garden Inn Annapolis Downtown

Annapolis

10/10 Excellent

Nice hotel in a very central part of town

Francesco

Reviewed July 8, 2026Reviewed July 8, 2026

Hilton Garden Inn Annapolis Downtown

A modern lobby with a reception desk, seating area, and potted plants.

A hotel dining area with multiple tables and chairs, large windows, and a chandelier.

A modern hotel lobby with a sectional sofa, round ottomans, a chandelier, and large windows.

An outdoor patio with tables and chairs, a brick floor, and a building with a green roof in the background.

Hilton Garden Inn Annapolis

Annapolis

10/10 Excellent

Shane

Reviewed November 2, 2026Reviewed November 2, 2026

Hilton Garden Inn Annapolis

An outdoor patio with tables, chairs, and a fire feature.

A modern living room with a fireplace, a sofa, and a coffee table.

A modern dining area with multiple tables and chairs, large windows with a view of greenery, and decorative wall mirrors.

A modern lounge area with a sofa, round tables, and chairs, featuring geometric wall decor and large windows.

Fairfield Inn & Suites By Marriott Annapolis

Annapolis

10/10 Excellent

Rooms are clean, comfortable and give you a cool non-boxy vibe

Ben

Reviewed December 5, 2025Reviewed December 5, 2025

Fairfield Inn & Suites By Marriott Annapolis

A modern hotel kitchen with a central island, seating area, and various kitchen appliances.

A Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

A hotel lobby with a reception desk, seating area, and dining space.

A hotel room with a large bed, a desk with a laptop, a television, and a door with a curtain.

Best Western Annapolis

Annapolis

10/10 Excellent

Room was clean but smells old. Air conditioning was working well. Checked in was just okay. The front desk staff was not friendly and never smiled. Very intimidating. The staff in the breakfast buffet was very nice and friendly. We’ve been coming in BW once or twice a year. Nice location.

Ermelita

Reviewed September 13, 2026Reviewed September 13, 2026

Best Western Annapolis

A hotel lobby with a reception desk, seating area, and artwork on the walls.

A bar area with multiple seating options, including bar stools and tables, and a variety of bottles and glasses on shelves.

An outdoor seating area with tables and chairs, blue umbrellas, and a brick building in the background.

A hotel lobby with a long bar area, seating, and a projection screen.

Comfort Inn Conference Center

Bowie

10/10 Excellent

I appreciate the location for my purposea. Comfortable, quiet, pleasant personnel.

Maureen

Reviewed September 10, 2024Reviewed September 10, 2024

Comfort Inn Conference Center

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Search Condos Rentals in Highland Beach from CA $282

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Highland Beach condo rentals

1. Upscale Condo in Annapolis w/Private Parking

2. Chapel Gate 3BR Steps to City Dock & Naval Academy

3. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Top reviews in Highland Beach

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

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