Fitness-friendly holiday rentals in Chesapeake

Find and book unique fitness-friendly rentals on Airbnb

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 2,840 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 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 Cinema Cafe-Greenbrier Mall

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
A spacious balcony offers unobstructed ocean views, overlooking the sandy beach and calm waters. A single black wicker chair is positioned on the balcony, providing a comfortable spot to enjoy the scenery. Bright blue skies enhance the coastal atmosphere.
Flat in Virginia Beach
4.73 out of 5 average rating, 37 reviews

OceanSands Balcony Bikes Chairs:ALLFees Included

This is a oceanfront 1bedroom, 1 bathroom unit with balcony or walkout patio on the Oceanfront. Unit features a shower & tub in bathroom, kitchen, dining area, living room with pull out sofa, oceanfront bedroom with six foot deep balcony. Bike & beach chair use/ aquarium admission is exclusive to this listing on reservations of 2+nights. Please inquire before arrival. No pets, parties, or smoking. Guest checking in must be 21 or over with a bank card for a temporary hold against incidentals.

Superhost
A fire pit surrounded by five colorful Adirondack chairs is set on a gravel circle by the water's edge. The calm waters of Hampton Roads Bay stretch out in the background, providing scenic waterfront views under a clear blue sky.
Home in Portsmouth
4.93 out of 5 average rating, 59 reviews

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.

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, 33 reviews

Sun & Fun! Ocean/Bay views /3 pools, gym, arcade

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, 2 gyms, local restaurants and much more! WE HAVE ADDED AN ARCADE!

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
4.96 out of 5 average rating, 51 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
4.9 out of 5 average rating, 63 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.

Guest favourite
Apartment in Sandbridge
4.94 out of 5 average rating, 159 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!

Superhost
Apartment in Sandbridge
New place to stay

NEW Updated! Oceanfront / Pool / Beach / Fishing

Oceanfront Luxury Condo | Pool Views | Steps to Sandbridge Beach NEW DESIGNER FURNISHINGS Welcome to Salt & Serenity, a beautifully updated 2 Bedroom, 2 Bathroom oceanfront condo complex located at The Sanctuary at False Cape in Sandbridge Beach, Virginia Beach. Wake up to breathtaking Atlantic Ocean sunrises as you stroll on the beach, enjoy coastal breezes from your private balcony overlooking the pool, and just steps from one of the most peaceful and beautiful beaches on the East Coast.

Top guest favourite
A wide sandy beach stretches alongside gentle ocean waves under a clear blue sky. Colorful resort buildings line the beach, creating a welcoming coastal atmosphere. Footprints in the sand suggest leisurely strolls along the shore, inviting relaxation in this serene setting.
Flat in Sandbridge
5 out of 5 average rating, 47 reviews

Bayside condo on the beach in Sandbridge

Welcome to Bayview Beauty, a luxury condo located in beautiful Sandbridge beach at the resort complex, the Sanctuary at False Cape. There are 3 onsite pools, 2 gyms, Viking grills in the courtyard, and an on-site restaurant. The resort is located right on the beach, so no roads to cross to get to the ocean and our spectacular beach. Our condo is bayside, with beautiful water views of the protected waters of the Back Bay. Enjoy summer breezes and stunning sunsets from a private balcony.

Guest favourite
The entrance features a light-colored door adorned with a welcoming wreath. To the right, a sign displays the property name 'All4One' alongside the Virginia shape. The brick facade showcases a warm, inviting exterior, complemented by a traditional lantern mounted beside the door.
Home in Virginia Beach
4.8 out of 5 average rating, 170 reviews

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!

Top guest favourite
Camper van/Motorhome in Sandbridge
4.96 out of 5 average rating, 53 reviews

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.

Superhost
A living area features a navy blue sofa, topped with soft decorative pillows, flanked by two striped armchairs. A wooden coffee table sits at the center, while a small bar area with a black stool is visible to one side. Tall windows with dark curtains allow natural light to enter.
Flat in Virginia Beach
4.63 out of 5 average rating, 191 reviews

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.

Top 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
4.94 out of 5 average rating, 143 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!

Popular amenities for fitness-friendly rentals in Chesapeake

When is the best time to visit Chesapeake?

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Avg. price$116 SGD$123 SGD$129 SGD$133 SGD$134 SGD$150 SGD$168 SGD$164 SGD$116 SGD$127 SGD$149 SGD$145 SGD
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