Holiday rentals with a pool in Delaware Bay

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Top-rated rentals with a pool in Delaware Bay

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

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Top Guest favourite
An expansive outdoor pool is set against a backdrop of lush greenery and trees. Warm lighting from the stone cottage bathes the area in a soft glow, creating a tranquil ambiance in the early evening. The pool's water reflects blue hues, inviting a sense of relaxation.
Cottage in Wrightsville
4.96 out of 5 average rating, 186 reviews

-The Pool Cottage at The Roundtop Estate-

Experience the ultimate private, romantic retreat tucked away from the hustle and bustle. Our unique hideaway offers over a mile of seclusion from the nearest road, immersing you in nature’s quiet beauty. Relax in the Brand-new Saltwater pool and hear the gentle hums of a train rolling along on the other side of the river. Indulge in the luxurious amenities our property has to offer. Rejuvenate in the hot tub, or warm up by the Breeo Firepit with a Latte from the Breville Espresso Machine.

Top Guest favourite
The exterior of a custom-built tiny house is displayed, featuring a combination of horizontal siding and large windows. Two yellow chairs with a small table sit on the porch, framed by surrounding greenery, creating a connection to the natural environment.
Tiny home in Lincoln
4.87 out of 5 average rating, 326 reviews

Tiny house w/ Pool on water near Beaches / turf

Enjoy a peaceful waterfront stay in our custom-built tiny house, located on Cedar Creek just off Route 1. Conveniently situated only 10 minutes from Delaware Turf and 15 minutes from the beach. The home comfortably sleeps four and includes hot tub access. We live on-site and are happy to assist throughout your stay. Ideal for families, pets (please review rules under “The Space” section), contractors, and long-term renters. Perfect for travel nurses & remote workers – Monthly stays welcome!

Superhost
An A-frame tiny home is shown at dusk, featuring warm exterior lighting. The front porch is surrounded by a wooden deck with two chairs, inviting relaxation. The structure is framed by trees, blending with the natural surroundings.
Tiny home in New Holland
4.92 out of 5 average rating, 103 reviews

Waterfront A-Frame Tiny Home at Red Run - Site 116

You'll love this unique and romantic escape. Enjoy a lakefront view in serene Amish Country Lancaster County, Pennsylvania. Nestled around the lake at Red Run Campground, enjoy a cup of coffee on the porch of your tiny home - or wet your fishing line in this catch and release fishing pond! The A-Frame Tiny Home features 1 bedroom, 1 full bathroom, kitchenette, and living room, as well as deck & firepit area. Also enjoy all of the amenities at Red Run Campground - including a pool (seasonal)!

Top Guest favourite
Guest suite in Annapolis
4.94 out of 5 average rating, 126 reviews

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a private ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a deadbolt; no shared indoor spaces; separate entrances).

Top Guest favourite
The charming cottage features a white exterior with a brown roof and brick chimney. Lush green trees and plants surround the home, providing a tranquil setting. A small garden area is visible in the foreground, enhancing the natural appeal of the landscape.
Home in New Hope
5 out of 5 average rating, 213 reviews

Charming cottage

Welcome to this over 100 yr young charming cottage located betw New Hope Boro and Peddlers Village. Completely updated and renewed, this stylish open floor plan cutie has all new appliances, offering Bertazonni stove, Pfisher & Pakel fridge &much more! Two generously sized bedrooms on the upper level, full bathroom on first floor. Exquisite views of the professionally landscaped spacious rear yard and in ground pool with lg deck overlooking the grounds & charming paths to guide you thru

Top Guest favourite
An aerial view showcases the expansive riverfront property surrounded by lush green fields and waterways. The deep Cohansey River meanders through the landscape, reflecting the sky. Various shades of green and water create a tranquil and serene environment.
Home in Bridgeton
4.99 out of 5 average rating, 276 reviews

THE SORA with Disco, Hot Tub & Pool

Immerse yourself in the timeless beauty of this 12 acre riverfront property. Experience the peaceful beauty of 800+ feet of direct river frontage on the deep Cohansey River. This river leads to the Delaware Bay/ Atlantic Ocean. Situated on the site of the Prestigious Sora Gun Club, this historic 4 Bedroom, 2 1/2 Baths light-filled home with magnificent great room has classical details and distinctive appointments. One of the 4 bedrooms and the 1/2 bath is in the 2 story guest house.

Guest favourite
An inviting saltwater pool is bordered by lounge chairs, with colorful floats resting on the water's surface. Surrounding scenery features lush greenery and a vibrant sunset sky, casting warm hues over the space. The area is designed for relaxation and enjoyment.
Home in Cape May
4.89 out of 5 average rating, 129 reviews

Mimosa Salt Water Pool & HOT TUB Oasis, Sleeps 8

Just Renovated!Linens and Towels INCLUDED! Perfect for 2 families a King & Queen Bedroom and the third bedroom comes w/a full/twin bunkbed that has a twin pull out in addition to a twin bed. (Sleeps 8 total) In ground Salt Water Pool perfect for relaxing all day w/your kids if beach is too much of a chore or having dinner outside. Our yard is fenced in and perfect for your furry friend. Open concept living room, dining room and kitchen. Great for coming together and socializing

Top Guest favourite
A spacious living room features a large sectional sofa and a floor-to-ceiling gas fireplace. Natural light filters through the plantation shutters, highlighting decorative plants and a round mirror. A large TV is mounted above a white-brick fireplace, creating a cozy gathering space.
Home in Villas
4.99 out of 5 average rating, 166 reviews

Hot Tub Backyard Oasis, Private Beach, Local Pool

Start your morning soaking in the hot tub, or sipping coffee in rocking chairs on the front porch. Just 1 block away, have the beach all to yourself in this truly secluded beach neighborhood. Enjoy one of the local waterfront eateries or the neighborhood pool. Spot a school of dolphins under a red-sky sunset before returning home to enjoy the night sea breeze and a movie in front of a wood burning fire in the outdoor gazebo. Click our icon to check out our other Cape May homes!

Top Guest favourite
A spacious outdoor area features a private saltwater pool surrounded by a paved patio. Several lounge chairs and umbrellas offer shaded seating around a dining table. Neatly maintained gardens enhance the atmosphere, providing a serene backdrop for relaxation.
Home in North Cape May
4.98 out of 5 average rating, 242 reviews

Villa By the Bay NOW OPEN Heated Pool & Hot Tub

PRIVATE HEATED SALT WATER POOL NOW OPEN UNTIL 10/30/26 HOT TUB OPEN YEAR ROUND! EVERYTHING YOU NEED FOR THE PERFECT VACATION! ALL LINENS/TOWELS PROVIDED. We offer you a coffee and Tea Bar, Snacks to get your vacation off to the right start and a Welcome Gift to thank you for coming! Just mins from the Bay & the Heart of Cape May! We are close to restaurants and Wineries. Just a short walk to the Delaware bay. Beautiful fenced in back yard with outdoor grill and shower

Top Guest favourite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in Saint Michaels
4.97 out of 5 average rating, 188 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Top Guest favourite
A silhouette of a person stands on the sandy beach, arms extended towards the sunset. Gentle waves lap at the shore, reflecting warm hues of orange and pink as the sun dips below the horizon, creating a serene coastal atmosphere.
Home in Cape May
4.98 out of 5 average rating, 132 reviews

Beach block cottage • Cape May sunset bay access

Walk just 1 block to bay sunsets, then come home to a private backyard retreat with fire pit, outdoor kitchen, and bonus spaces you won’t find anywhere else. The main house offers 2 bedrooms, plus a separate camp-style cabin for extra sleeping. Enjoy your morning coffee in the screened-in Zen Den or unwind outside under the stars. A unique, laid-back Cape May stay—perfect for couples, families, and small groups who want space, character, and a true getaway feel.

Top Guest favourite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville
4.99 out of 5 average rating, 336 reviews

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Popular amenities for Delaware Bay rentals with a pool