Fitness-friendly vacation rentals in Chesapeake

Find and book unique fitness-friendly rentals on Airbnb

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

  • Total vacation rentals

    Explore 110 vacation rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,840 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Chesapeake vacation rentals include wi-fi 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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Guest favorite
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
4.95 out of 5 average rating, 57 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 favorite
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.
Condo in Sandbridge
5 out of 5 average rating, 30 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 favorite
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
4.98 out of 5 average rating, 43 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.

Guest favorite
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.
Guesthouse in Virginia Beach
4.92 out of 5 average rating, 60 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 favorite
Condo in Sandbridge
4.94 out of 5 average rating, 157 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 favorite
Home in Moyock
4.96 out of 5 average rating, 49 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!

Guest favorite
The exterior of the property showcases a two-story brick structure alongside a single-story home, surrounded by trees and greenery. A driveway provides access, with a garage door visible. Natural light illuminates the scene under a clear sky.
Apartment in Chesapeake
4.95 out of 5 average rating, 94 reviews

1 King Master BR. ⚡️Fast Wifi. 🔐 Easy Self Check In

Welcome to Casa de Curtin - a 1Br Apt. Oasis Perfect for Vacationing Couples! Downstairs features a full kitchen w/ dbl sink, refrigerator, washer, dryer, range, microwave, Keurig, table & chairs. The living room has a plush, oversized sofa & chair set & an HD TV w/ Firestick & fast WiFi. Upstairs has a spacious br w/ ceiling fan, central air & window unit + large full bth w/ fan. Smart locks make self check-in a breeze! Located close to VA Beach, ODU, & <1h drive to Williamsburg.

Top guest favorite
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.
Apartment in Sandbridge
5 out of 5 average rating, 45 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.

Top guest favorite
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, 141 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!

Superhost
A large window frames a view of the ocean, showcasing sandy beach umbrellas and beachgoers below. Natural light fills the room, highlighting a glass table and a chair nearby. The air conditioning unit adds functionality to the space.
Apartment in Virginia Beach
4.66 out of 5 average rating, 157 reviews

* Penthouse on Atlantic Ave* 2bdrm

This penthouse is on the 6th floor of the Days Inn Motel and is across the street from the beach. Enjoy the pool (mid April-Sept) and gym on the 1st floor. It's located in the resort, close to many activites,shops and restaurants. Beach Coffee downstairs makes the best Avocado toast and Acia bowls and of course coffee! Il Giardino Ristorante is next door and offers upscale Italian dining. Bike/surrey rentals are close by and enjoyed along the oceanfront on the bike path.

Guest favorite
Condo in Sandbridge
4.88 out of 5 average rating, 265 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, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Top guest favorite
Tiny home in Sandbridge
5 out of 5 average rating, 58 reviews

Waterfront Tiny Home-Pool-Kayak-Pets-Pickleball

Relax in comfort while enjoying water views so breathtaking it feels like you are on a boat! The most amazing sunsets in all of Sandbridge will be yours. Enjoy the best of both worlds – the beach and the bay – at your own private waterfront refuge. After enjoying the sun and surf at the beach, retreat to your own oasis to recharge while you soak up the views, take a paddle on the bay, or land the catch of the day! 180 degree bay views and incredible sunsets await.

Popular amenities for Chesapeake fitness-friendly rentals

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$18,828 GYDG$19,874 GYDG$20,920 GYDG$21,548 GYDG$21,757 GYDG$24,267 GYDG$27,196 GYDG$26,569 GYDG$18,828 GYDG$20,502 GYDG$24,058 GYDG$23,431 GYD
Avg. temp6°C7°C10°C16°C20°C25°C27°C26°C23°C18°C12°C8°C

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