
Vacation 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.

Glamping Vibes Cabin~HotTub/Gazebo1.5~NYC/1~Philly
365 days/year~ Hot tub/104°F. Relaxing & romantic getaway. Comfort of a cabin with an atmosphere of camping. An Experiential get-away/private gated/fenced property. Gazebo~plastic panels, insect netting, outdoor furniture,gas firepit & hot tub. Detached luxury bathroom behind cabin.Outdoor shower, Hammock, BBQ’s, Wood firepit. Reconnect w/the outdoors.Queen bed w/firm mattress.Escape the cities to privacy. Abutted on 3 sides by a farm/pasture views.Easy to get to from points east in NYC & Philly

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!

Historic Rousby Hall, Waterfront, Pool, Beach
**Heated pool open to Nov 2. Thanksgiving chef dinner options** Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

Mill Road Farmhouse: Restored with Beautiful Pool.
The Mill Road Farmhouse is a destination in and of itself. Immaculately restored inside and out, this home is a true retreat in the middle of Amish Country. We have a feeling you will be spending all of your time relaxing by pool and hot tub during the warmer months (or maybe grilling up a feast in the brand new outdoor kitchen area) and curled up next to one of the four indoor fireplaces during the winter months. And then of course end each day star-gazing while sitting around the campfire.

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 3 Bedroom, 2- Baths light-filled home with magnificent great room has classical details and distinctive appointments. Additional 2 story building available to bring guest count from 8-12 w/ 1/2 bath

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

Garden of Zen
Secluded, clean, light & airy studio unit in a garden setting. Situated in a quiet neighborhood, best suited for peace and relaxation. Studio has it's own deck & yard, and pool area is essentially private also. Location has great access with GSP exit/entrances a minute away. Somers Point restaurants and bars are also just minutes away. Area has great opportunities for kayaking, biking, & the beach This rental prioritizes a clean & healthy ambiance. No cigarette smoking.

Cozy Woodland Cottage
Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.

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.

Silo Suite
Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

Waterfront Getaway - 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.

Beautiful Waterfront Home-Private, Clean, Relaxing
A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* from Memorial Day to Labor Day.
Popular amenities for Delaware Bay rentals with a pool
House rentals with a pool

Idyllic estate, close to downtown and the Amish.

307+ Five Star Reviews Near Hershey w/ Hot Tub!

Gunpowder Retreat

Mimosa Salt Water Pool & HOT TUB Oasis, Sleeps 8

Beach Retreat w/ Fire Pit, Camp Cabin & Zen Den

The Little Gypsy BoHome

The Villa By the Bay-Private Heated Pool & Hot Tub

Adorable Avalon House | Private Pool
Condo rentals with a pool

Bluewater Couples Escape

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Cozy Wildwood Crest Beach - Poolside Condo

Spacious| Modern &Cozy| Pool| Close to the Beaches

2b 2b condo! 2 master bedrooms! rehoboth beach

Modern 2BR/2BA – Beach Pass + Bikes, 5 Min Drive

Ocean Pines Retreat

Beachfront with a View and Amenities Galore
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Flohom 1 | Breathtaking Skyline 360° Views

Oceanfront - Center of Town - Pool

1st Floor 2BR/2BA | Pool | Quiet & Convenient

Private Country Guesthouse Getaway Minutes from UD

Amazing oceanfront view 3 blocks from boardwalk

Lewes Carriage House- Reflect. Recenter. Renew.

Casa al Mare - Beautiful 2 bdr on the Beach Block!

Woodland Retreat
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