Holiday rentals with a pool in Cambridge

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cambridge

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in Ridge

4.89 out of 5 average rating, 56 reviews

Waterfront Paradise with a Private Pool

Set on three acres of spectacular waterfront property, there’s everything you need to escape – a dock, a fire pit, crab traps, kayaks, bikes and a POOL. Next door: 20 acres of unkempt forest where bald eagles fly. The pool is closed until end of April and is not heated. The home is warm, unpretentious, with a minimalist approach to décor but a stocked kitchen for those who love to cook. Amenities: a HDTV with premium channels, high speed internet, a ping pong table, lawn croquet and more.

Guest favourite

Cottage in Royal Oak

5 out of 5 average rating, 11 reviews

Newly Renovated Summer Paradise-Pool-Tennis-Garden

Our newly renovated garden cottage is nestled on an 18 acre waterfront private retreat with access to a swimming pool, gym, tennis court & private dock! The kitchen is fully-equipped with stainless steel appliances and laundry located in house. The cottage shares the grounds with a few other of our private cottages. Guests also have access to kayaks, fishing equipment, the fire pit, ice cream shop, library and more! Quiet and remote but very close to both Easton and Saint Michaels for a perfect

Guest favourite

Guest suite in Arnold

4.87 out of 5 average rating, 133 reviews

Cozy Comfort - only 7.5 Miles to Annapolis & USNA

Close to historic Annapolis, our cozy first floor guest apartment of our home in a quiet large single family home neighborhood. 'The Oasis' is private and spacious with 2-bedrooms, a living room, mini sit-in kitchen, bathroom, and laundry room. Close to waterfront restaurants, B & A trail, Sandy Point Public Beach and Park, festivals, shopping, bowling, miniature golf, wineries and more. Our guests are welcome to enjoy some time relaxing in our wooded backyard with pool (unheated) and gazebo.

Top guest favourite

Flat in Stevensville

4.98 out of 5 average rating, 274 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Guest favourite

Home in Stevensville

4.95 out of 5 average rating, 87 reviews

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Superhost

Home in Lewes

4.78 out of 5 average rating, 45 reviews

Bring your flip flops and relax! Adorable beach cottage in a quiet, gated community just a short drive from the hustle and bustle of downtown. Enjoy the outdoor area at home with a fire pit, grill, and games or explore the wooded trails, crabbing dock, or community pool. The pool is open on weekends only from the Saturday of Memorial Day weekend until full-time hours begin on or about the 12th of June each year. CLOSES Labor Day weekend. You must be at least 25 years of age to rent.

Guest favourite

Flat in Arnold

4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Guest favourite

Home in Montross

4.93 out of 5 average rating, 202 reviews

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

Guest favourite

Home in Edgewater

4.98 out of 5 average rating, 65 reviews

Waterfront | Pool | Hot tub | Beach Access

Pool is open. Recently renovated home near gorgeous Chesapeake Bay beaches! Located on a quiet street between Beverly Triton Nature Park and Mayo Beach Park. Your Big Pond retreat has a primary king suite, private pool, hottub, pond access & an expansive outdoor living area! This luxurious open floor plan living is on one level & sleeps 8. Less than 25 minutes from downtown Annapolis with amazing shopping & restaurants with a view! The perfect getaway for fun & relaxation.

Top guest favourite

Home in Rehoboth Beach

5 out of 5 average rating, 19 reviews

Pet friendly house w/shared pool, slide & hot tub

New pet friendly LVP floors for 2024! Relax with the whole family - and your dog too! This cozy and comfortable house is located just a couple of miles from the Rehoboth Boardwalk. It has 3 bedrooms, 2 baths, a spacious living room, a fully equipped kitchen, and a private deck. Next door, you have semi-private access to a pool with a waterslide and hot tub. You can enjoy relaxing poolside or soaking in the hot tub after a day of fun at the beach.

Top guest favourite

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Superhost

Home in Port Republic

4.75 out of 5 average rating, 20 reviews

Family Friendly: Hot Tub, Grill, Pool & More!

*POOL IS OPEN* Discover paradise in our vacation gem – where luxury meets modern living. Nestled in a serene, private neighborhood, this retreat boasts 5 trendy bedrooms and 3.5 Insta-worthy bathrooms, accommodating 10 guests. Indulge in resort-style leisure with a pool, spa, and lush landscaping – a backdrop for selfies. #VacayGoals