Fitness-friendly holiday rentals in Chesapeake

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Top-rated fitness-friendly rentals in Chesapeake

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness and more.

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Superhost
Apartment in Sandbridge
4.75 out of 5 average rating, 4 reviews

Sunset Bay - Gorgeous Bay and Sunset Views.

Welcome to your perfect Sandbridge escape - Sunset Bay. This beautifully updated 2 bedroom, 2 bathroom oceanfront condo offers the ideal blend of coastal comfort and modern style. It was recently renovated from top to bottom. From the furnishings and décor to the fresh paint and finishes, it creates a bright, clean, and welcoming space for your stay. The highlight of the condo is the stunning wall of windows and balcony overlooking the bay, showcasing breathtaking sunset views each evening. Relax with a drink as the sky lights up in vibrant colors, or enjoy your coffee in the peaceful mornings watching the water come alive. Both bedrooms are designed for comfort and relaxation, making this condo perfect for families, couples, or friends traveling together. The open living and dining areas provide plenty of space to unwind after a day at the beach, while the oceanfront location means you’re just steps away from the sand and surf. The kitchen features granite countertops and stainless steel appliances. The essentials for cooking are provided: cookware, dinnerware, glassware, and utensils. Enjoy your meals at the dining table, or take advantage of the grills and seating in the courtyard. *Important note: The coffee maker listed under amenities is a Keurig. The Sanctuary at False Cape offers a resort feel with direct beach access,3 swimming pools (seasonal), 2 fitness rooms, and 2 nearby restaurants. The complex (not the unit)is oceanfront and the beach can be accessed without crossing any roads. Beach chairs are available for use in the private storage unit located at garage level. Jose Tequilas Mexican Grill and Bar is located on the property, and Baja Restaurant (closed for a few weeks during the winter season)is located across the street. Set in the quiet and scenic Sandbridge community, this condo offers a true beach getaway with uncrowded beaches, natural surroundings, and easy access to outdoor adventures while still being a short drive from the attractions of Virginia Beach. Whether you’re planning a relaxing retreat or a memorable coastal vacation, this oceanfront condo with stunning bay sunsets is the perfect place to call home. Important Notes: The minimum age to rent is 25. At least one person who is 25 years or older must be staying at the property for the duration of the rental. The Sanctuary at False Cape is a non-smoking property. Smoking (of any kind) is prohibited in the unit, on the balcony, and in the common areas of the property. Pets are not allowed. No parties or events allowed in the unit. Pools are managed by the condo association. Availability is subject to weather, maintenance, and/or repairs. Unit comes with two parking passes. One is an assigned space and the other is a first come first serve unmarked space. Garage clearance is 7'4". Additional public parking is located next door at Little Island Park and Fishing Pier (fee applies). As owners, we just received the following notification: Please be advised that the community power washing and painting project is scheduled to begin on March 9, 2026. This work is part of our ongoing building maintenance program to preserve and enhance the property's exterior condition. The contractor will begin mobilization and scaffolding setup starting March 9, with power washing and painting activities continuing through Memorial Day. To minimize disruption during the peak summer season, the project will pause for the summer months and resume at the end of the season. During this time, there may be intermittent impacts to certain exterior areas, including scaffolding, lift equipment, and active work zones.

Guest favourite
A wide, sandy beach is outlined by spacious condos in soft pastel colors against a clear blue sky. Fishing rods are positioned in the sand near beach carts, indicating a relaxed atmosphere. Waves gently lap at the shoreline, creating a tranquil coastal setting.
Apartment in Sandbridge
4.87 out of 5 average rating, 258 reviews

Ocean Escape

Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Top guest favourite
Two wooden adirondack chairs are placed on a stone patio, each adorned with a green tropical patterned pillow. A calm waterway is visible in the background, flanked by trees and a building. Bright blue skies add natural light to the scene.
Tiny home in Sandbridge
4.97 out of 5 average rating, 34 reviews

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.

Superhost
A rustic stone fireplace serves as a central feature in the living area, its warm glow inviting relaxation. The high ceiling and exposed beam accents create a spacious atmosphere, complemented by hardwood flooring and comfortable seating arrangements nearby.
Guest house in Virginia Beach
4.91 out of 5 average rating, 54 reviews

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.

Top guest favourite
Apartment in Sandbridge
4.93 out of 5 average rating, 148 reviews

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!

Top guest favourite
Home in Moyock
4.95 out of 5 average rating, 44 reviews

3BR Coastal Townhome w/ Gym & Sauna |Near VB & OBX

Welcome to our spacious 3-story coastal townhome, centrally located between Virginia Beach and the Outer Banks. This 3BR, 2.5BA home features a bright open living area, fully equipped kitchen, and dining space. The first floor offers a cozy sitting area plus a private home gym with a one-person portable sauna. The third floor includes three bedrooms, including a primary suite with walk-in closet and ensuite bath. Washer and dryer provided. Perfect for weekend getaways, beach trips and more!

Superhost
An expansive wraparound porch showcases comfortable outdoor seating, inviting relaxation. A wooden table rests in the center, and panoramic views of the ocean and vibrant sunset are visible through open railings. The gentle glow of twilight enhances the tranquil coastal ambiance.
Flat in Sandbridge
4.8 out of 5 average rating, 25 reviews

New! Oceanfront Penthouse/ 2 Decks/ Pool/Beach/Gym

Bayfront Dream Penthouse | Oceanfront Luxury with Wraparound Porch & Resort-Style Amenities Welcome to Bayfront Dream Penthouse! A luxurious oceanfront two-level retreat overlooking the tranquil waters of Back Bay/Albemarle Sound. This newly decorated 4-bedroom, 4-bathroom penthouse offers stunning views, elegant interiors, and exclusive access to resort-style amenities, making it the perfect getaway for families, couples, or groups looking for an unforgettable beach retreat.

Guest favourite
A sunset casts warm hues over the calm waters of the bay, with silhouettes of a shaded gazebo and a hammock. Weathered pilings and a single bird in flight can be seen against the vibrant sky, enhancing the tranquil atmosphere.
Home in Knotts Island
4.93 out of 5 average rating, 136 reviews

Island Lotus Yoga & Spa

A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

Top guest favourite
A spacious balcony features several blue adirondack chairs, offering a view of the surrounding buildings and the outdoor area. Clear skies with a few clouds create a bright atmosphere. The ocean is visible in the distance, providing a scenic backdrop.
Apartment in Sandbridge
5 out of 5 average rating, 26 reviews

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym

The VIEWS are EVERYTHING! You have to see it to believe it! This is a NEW listing. Please see my other property for reviews! I frequently travel for work, spending a lot of time in hotel rooms. I know the NECESSITIES! Relax with the whole family at this peaceful place to stay in Sandbridge! Wake up to the sun rise over the ocean and wind down with the sunset over the bay! This property is ON the beach with access to 3 pools, a gym, local restaurants and much more!

Superhost
A charming duplex is presented with a well-maintained lawn and shaded path leading to the entrance. The façade features a combination of brick and siding, complemented by neatly trimmed hedges on either side of the entrance steps. A patio with furniture is visible to the right.
Home in Portsmouth
4.86 out of 5 average rating, 65 reviews

Near Casino, VA beach, Large yard, quite relaxing

Spacious home and quiet neighborhood. 3.5 miles to Naval Medical Center. 3.5 miles to Norfolk Gen. Hospital. 3 miles to Roger Browns. 5 miles to Norfolk Waterside District. 2 miles to Rivers Casino. 22 miles to VA beach. Sleeps 6-7 people. All essentials provided. Your home away from home. Check-in/out times may be flexible. Please read all the details prior to booking. Thank you for choosing Veronica Homes located in Portsmouth VA

Guest favourite
A dining table is set with an array of fresh fruits and cheeses, complemented by a vibrant blue arrangement of hydrangeas and two blue candles. The ocean can be seen in the background, enhancing the inviting beachside dining experience.
Apartment in Sandbridge
5 out of 5 average rating, 10 reviews

Oceanfront Condo with Balcony & Pool

Escape to Surf's Up, your oceanfront 3-bedroom condo! Enjoy stunning water views from your private balcony, just steps from the sand. This exceptionally clean home comfortably fits 6 and provides everything you need, from a complete kitchen to beach chairs and towels. As one guest said, 'Amazing view and literally minutes to the sand.' Perfect for families seeking a relaxing coastal getaway.

Top guest favourite
Home in Corolla
5 out of 5 average rating, 38 reviews

Oceanside Heated Private Pool HotTub Dogs Welcome

Escape to Golden Dunes, a pet-friendly oceanside cottage in Corolla for 10. This 4BR/3.5BA retreat features a private heated pool, hot tub, and distant ocean & lighthouse views. Enjoy a dedicated workspace, high-speed WiFi, and a short walk to the beach and lighthouse. Located where the paved road ends, it's the perfect base for your Outer Banks adventure, with or without a 4x4.

Popular amenities for fitness-friendly rentals in Chesapeake

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$128 SGD$128 SGD$141 SGD$132 SGD$134 SGD$149 SGD$167 SGD$163 SGD$116 SGD$126 SGD$148 SGD$144 SGD
Avg. temp6°C7°C10°C16°C20°C25°C27°C26°C23°C18°C12°C8°C

Quick stats about holiday rentals that are fitness-friendly in Chesapeake

  • Total holiday rentals

    Explore 110 holiday rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,790 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    110 of Chesapeake holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesapeake rentals

  • 4.8 Average rating

    Chesapeake stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Chesapeake’s top spots include Chrysler Museum of Art, Nauticus and Cinemark Chesapeake Square

Destinations to explore