Fitness-friendly vacation rentals in Chesapeake Beach

Oceanfront Penthouse | 4BR Sunrise & Sunset Views

Welcome to Penthouse Perspectives, newly renovated for 2026. Vacation in our stunning two-story oceanfront penthouse condo offering spacious luxury and breathtaking views of the Atlantic Ocean and Back Bay. Watch sunrises over the sand and sunsets over the bay from two oversized wraparound balconies. With four bedrooms, four bathrooms, and spacious kitchen and living area, this beautifully designed condo is perfect for family vacations and relaxing in ocean breezes. Step inside and be greeted by sweeping ocean views and an open floor plan filled with natural light from floor-to-ceiling windows. The living area flows seamlessly into the dining space and gourmet kitchen, which features stainless steel appliances, granite countertops, and a large island with seating for four. The adjacent dining area accommodates a large table, creating the perfect setting for meals together after a day at the beach. The second-floor primary suite is a private retreat, complete with a king-size bed, sitting area, coffee station, and its own private balcony overlooking the ocean. The luxurious ensuite bathroom includes a double vanity, soaking jacuzzi tub, and separate shower. The three additional bedrooms, located on the first floor, are generously sized and provide plenty of space and comfort for family and guests. Two are king beds with ensuite baths, and one bedroom with 2 bunk beds. Penthouse Perspectives offers two reserved parking spots next to the elevator. The large storage closet on the garage level houses chairs, an umbrella, and a beach cart for taking your belongings to the sand. The Sanctuary complex has three pools (one is oceanfront), two gyms, multiple outdoor grills and eating areas next to pool, and NEW for 2026: Sanctuary Arcade! Pool open annually from the beginning of June to the end of August for guest use. Pool dates and hours are weather permitting and at the Condo Association's discretion. Property Highlights: Oceanfront penthouse with stunning beach views 4 bedrooms | 4 bathrooms – ideal for families or groups 2 wrap-around private balconies overlooking the ocean Direct beach access just steps away Three community pools Outdoor grills and patio furniture in the common spaces Arcade Room Convenient parking and elevator access Outside your door, enjoy everything this oceanfront community has to offer, including direct beach access, three pools, an arcade, and common-area grilling stations. The building elevator is just steps away, making garage parking and trips to the beach or pool easy and convenient. Pool dates and hours are weather permitting and at the Condo Association's discretion. Whether you’re enjoying sunrise views from the balcony, spending the day on the beach, or relaxing by the pool, this exceptional penthouse offers the perfect blend of comfort, space, and unforgettable coastal views. Book your stay and experience coastal living at its best!

Oceanfront Beach Condo, Pool, Gym, Fishing Surfing

Wake up to ocean breezes, panoramic Atlantic Ocean views, and the soothing rhythm of waves in this modern 3 Bed, 2 Bth oceanfront condo on the Virginia Beach Boardwalk. Enjoy three private balconies for sunrise coffee and lovely sunsets, direct beach access, Indoor Heated Pool, Gym and Fitness Center, High-Speed Wi-Fi, and a fully equipped kitchen. Perfect for families or couples seeking a Virginia Beach Oceanfront Vacation Rental, steps from dining, attractions, festivals, and endless beach fun

Casa del Sueno

Casa del Sueno is the perfect way to enjoy life on the Back Bay to the Beach! This tiny house sits on the waters of the Back Bay National Wildlife Refuge in the quaint community of Surfside at Sandbridge. The view is ever changing natural beauty from either inside or outside on the deck. Take a walk or bike ride to the most beautiful beach along the Atlantic. Enjoy sunset, serenaded by live bands from a local watering hole within walking distance. Wake up & stroll across to watch the sunrise.

Waterfront/Arcade/Fishing Fun

Escape the hustle and bustle of daily life and immerse yourself in the serene beauty of nature at this remarkable retreat. Nestled overlooking the Bay, this tranquil getaway offers a haven for relaxation and rejuvenation. Wake up to the gentle sights of seabirds and waves lapping against the shore as you sip your morning coffee on the pier or watch the amazing sunsets. Try your hand at fishing. Leisurely stroll, breathing in the crisp, salty air and feeling the warmth of the sun on your skin.

Key Lime Cabana at Surfside

Check into Key Lime Cabana – Your Ultimate Beach Getaway! New 2025! Escape to the tranquility and adventure of Surfside at Sandbridge, a beautifully remodeled waterfront camper nestled at the southern tip of Virginia Beach. Surfside is surrounded by the serene Ocean and Back Bay, Key Lime Cabana offers the perfect blend of peaceful retreat and outdoor adventure. Just minutes from Back Bay Wildlife Refuge and a short bike ride to scenic trails, Book Now, for a one-of-a-kind beach experience.

The Sportman's Lodge

The Sportsman’s Lodge is a rustic and relaxing modern getaway with all the conveniences you are accustomed to but surrounded by the gorgeous Back Bay Wildlife Refuge. Enjoy the relaxing countryside at this waterfront property, while still being only a short drive away from Sand Bridge Beach. If you are looking to get away from the standard Virginia Beach Boardwalk tourist experience and get back to nature, this is the place for you. Free kayaking to Back Bay, access to fishing and crabbing.

Ocean & Bay Views - Newly Renovated! Local Family!

Just steps away from the sand, "Carolina on My Mind" is a 2b/2ba oceanside condo at the exclusive Sanctuary at False Cape, the only Oceanfront complex at Sandbridge in Virginia Beach. You'll enjoy a private patio with both Ocean and Back Bay views. The condo features a large open-concept living space, and a fully equipped gourmet kitchen, and high end finishes. Free access to all condo amenities, including free parking, 3 pools, grills, and a fitness center! Your beach vacation awaits!

Four Sails - 1B/1BA - X-Large Oceanfront Balcony!

Overlooking the north end of the Virginia Beach boardwalk, with some of the best oceanfront views in Virginia Beach, Four Sails is a resort hotel property made up of Condo-style units, just steps from the beach. There's an Indoor heated Pool inside a large Atrium, an exercise room with a Sauna, large City View Sundeck / Terrace, and Katie’s 33rd Street Cafe provides on-site dining for breakfast, lunch, and dinner. There are also multiple dining options within very short walking distance.

Large 4BDR lock-off; 2 Kit; 2 LR; 4 BA; 2 Dining

Family sized 4BDR/4BA Lock off unit. Two living rooms. Two kitchens. At Greensprings you will be able to enjoy some rest and relaxation, lounging in your own private bath whirlpool, or stretching out in front of the electric fireplace. You can take a swim in either the indoor or the outdoor resort swimming pools, or enjoy a game of tennis, even at night, on the floodlit tennis courts. Of course, there is also plenty of great golfing at the resort-adjacent Nicklaus-designed golf course.

All 4 One | Beach Living

Come enjoy time at the beach in our seaside oasis! All4One is located on the semi-private beach of Croatan in Virginia Beach. This means that although you are but a bike ride away from the hustle and bustle of the Boardwalk, you also have the beach to yourself in a quiet neighborhood setting- best of both worlds right? We certainly think so! My grandma built this home in the 1960's and my husband and have called it home for over a decade. Come enjoy your stay at the beach at our home!

Waterfront On Back Bay In Sandbridge.

Waterfront w/private dock. 2 Bedrooms, 1 w/queen bed & 1 full sofa bed. 1 bathroom w/large tub-shower. Living area w/TV. Kitchen Table w/4 chairs, full size refrigerator, gas stove, microwave, toaster, and Keurig coffee maker. Equipped w/everything you need. Pots pans dishes etc. Outside has a covered porch that steps out to with your own private dock for fishing or relaxing. Outdoor grill. Also provided, 2 paddleboards, bodyboards, beach chairs, rusty bikes & beach cart. No smoking.

Flipflop friendly *block from beach*2bdrm/2ba

This casual apartment is in the resort area. Free parking spot 702. Gym/pool (open mid-April thru September) access. Walk to the fishing pier on 14th St. or to 5th St. to surf. There are many restaurants nearby including Side Street Cantina right next door and Beach Dogs down the street. Beach Coffee is a locals favorite, close by, serving avocado toast/acia bowls. This particular apartment has 2 separate entrances, off bedroom #1 and into the living rm from the back of the house.