
Fitness-friendly holiday rentals in Chesapeake
Find and book unique fitness-friendly accommodation 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 $17 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
110 of Chesapeake holiday 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.

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!

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!

Corolla Light Resort | Beach Access | Pools
Welcome to Red Sky at Night in Corolla Light Resort—your easy, coastal OBX escape just a short walk from the beach. This beautifully updated 3BR/3.5BA home blends relaxed luxury with everyday comfort, featuring multiple private decks, a bright open layout, and a fully stocked kitchen made for gathering. Enjoy full access to resort pools, tennis, pickleball, and more. Perfect for families or couples looking for beach days, sunsets, and a walkable Corolla location that truly has it all.

Chickahominy Riverside Guest Home By Williamsburg!
Our river-side guest house has everything you will need to enjoy your getaway! Enjoy the river, dock, two kayaks, paddle board, canoe, large game room, portable fire pit, playground, basketball goal and large outdoor sitting area with a gas grill. Located 5-20 mins from the finest wedding venues, nearby wineries; less than an hour to Richmond & 25 minutes to Colonial Williamsburg. Only steps to numerous historic plantations & a few miles from the Virginia Capital bike & walking trail.

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.

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!

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.

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
Popular amenities for Chesapeake fitness-friendly rentals
Fitness-Friendly apartment accommodation

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

Family Reunion? Sleep 24. Greensprings 8BR/8BA

Historic Powhatan Resort 2 Bdrm! Sleeps 6

Sojourn Ocean View Oasis Ocean & Bay Views

Westgate Historic Williamsburg One Bedroom

Luxury Oceanfront 2BR Condo Balcony Pool Kitchen

Bayside condo on the beach in Sandbridge

Four Sails - 1B/1BA - X-Large Oceanfront Balcony!
Fitness-friendly condo rentals

Wyndham Governor's Green (3 BD Deluxe)

Oceanfront Penthouse | 4BR Sunrise & Sunset Views

Sea Life | Walk to Beach & Heated Pool, Dogs OK!

Marriott's Manor Club Ford's Colony 2BD Villa Slee

Oyster & Pearl Beautiful New Single Level Condo

Dolphin Beach condo-amazing view and indoor pool

NEW! Prime Location @Beach Club -Tranquil Seascape

Lewis Villa | 2 Min Walk to Beach + Heated Pool
Fitness-Friendly Holiday House

June specials Htd pool/hotub, firepit oceanview

The Moor House 2.0 - Sound Front, Private Pool!

The 1903 Beach Club at Whalehead - Corolla OBX

Oceanside,Pool,Spa,PinBall,7MinWalk2Beach&Sound Ne

Waterfront, Stunning Views + Pool | Kayaks!

Priv. pool, hot tub, FREE cleaning&linens, QUIET

14th & Hoos

Oceanside Heated Private Pool HotTub Dogs Welcome
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $156 NZD | $165 NZD | $173 NZD | $178 NZD | $180 NZD | $201 NZD | $225 NZD | $220 NZD | $156 NZD | $170 NZD | $199 NZD | $194 NZD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Destinations to explore
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- Rentals with a fire pit Chesapeake
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- Rentals with pools Chesapeake
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- Pet-friendly rentals Chesapeake
- Rentals with beach access Chesapeake
- Condo rentals Chesapeake
- Rentals with a fireplace Chesapeake
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- Smoking-friendly rentals Chesapeake
- Fitness-friendly rentals Virginia
- Fitness-friendly rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Old Dominion University
- Regent University
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- Neptune's Park
- First Landing Beach
- Currituck Club
- Currituck Beach Lighthouse
- The Military Aviation Museum
- The Mariners' Museum
- Nauticus
- Back Bay National Wildlife Refuge-N





