
Holiday rentals with a pool in Delaware Bay
Find and book unique homes with a pool on Airbnb
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

Studio apt near DE turf, beaches, &hospital
Your family will be close to everything when you stay at our centrally-located place. We are just 2 minutes from bayhealth hospital Milford campus, 10 minutes from DE turf & 20-30 minutes from all beaches. Early check in available upon request for 12:00pm, fee $100. During the summer months we offer our pool for guest use! We welcome families & fur babies! We do have 5 dogs ourself that roam freely in our backyard. PLEASE READ CANCELLATION POLICY CAREFULLY Pets crated when unattended!

Relaxing Getaway
Enjoy the shore at this fully renovated luxurious beach house. This 3 bedroom 2 bath (with sleeper Sofa) can sleep up to 12 people. The space has been recently renovated. New kitchen, new bathrooms, brand new carpets, and hardwoods. An amazing in ground heated pool, with 8ft privacy fence highlight the back yard. The back yard also features ample seating, a fire pit, and a brand new 7 person hot tub. This is the perfect getaway for any family or families looking for fun at the jersey shore.

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

Hot Tub Holiday Escape! Fireplace + backyrd oasis!
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!

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.

Boutique suite, Palace in the Woods
The Palace in the Woods is a “ NO CHORES STAY AIRBNB “ just what you need for a peaceful visit to Cape May County BEACHES & BOARDWALKS . Located in the woods, just ten to fifteen minutes from Sea Isle, Avalon, and Stone Harbor, and the Cape May County ZOO - a little bit further to Ocean City, Wildwood and Cape May. A perfect location for beachgoers, birders, cyclists, and foodies. Please read house rules ( additional rules ). If you have any questions, feel free to ask.

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.

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.
Popular amenities for Delaware Bay rentals with a pool
House rentals with a pool

Creek front home *heated pool open year round!*

Wilde Rose By The Bay - Salt water Inground pool

Idyllic estate, close to downtown and the Amish.

Mystical Cape May's Modern Farmhouse: The Widmore

Waterfront Farmhouse Meets Modern Luxury

Beach Please! River cottage w/private beach & dock

Mimosa Salt Water Pool & HOT TUB Oasis, Sleeps 8

SeaLaVie! Pool! Hot tub! Huge Yard! Bay Sunsets!
Apartment rentals with a pool

Oceanfront Condo | NEW Retro Design | Beach + Pool

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Oceanfront Family Oasis: Pool, Beach & Parking!

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

Mimi’s Place @ The Villages of 5 Points in Lewes

Renovated Condo Near Outlets, 3.5 Miles to Beach

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

Ocean Pines Retreat
Other holiday rentals with a pool

Garden of Zen

Oceanfront - Center of Town - Pool

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Private Country Guesthouse Getaway Minutes from UD

Annapolis Garden Suite

Lewes Carriage House- Reflect. Recenter. Renew.

The Cozy Cottage At Grateful Meadows

Wilde Haven - Waterfront A-Frame Studio - Site 141
Destinations to explore
- Rentals with an EV charger Delaware Bay
- Private suite rentals Delaware Bay
- Waterfront rentals Delaware Bay
- Bed and breakfasts Delaware Bay
- Rentals with a patio Delaware Bay
- Guest house rentals Delaware Bay
- Flat rentals Delaware Bay
- Rentals with a firepit Delaware Bay
- Rentals with lake access Delaware Bay
- Boutique hotel rentals Delaware Bay
- Beachfront rentals Delaware Bay
- Hotel rentals Delaware Bay
- Rentals with a fireplace Delaware Bay
- Cabin rentals Delaware Bay
- Rentals with a hot tub Delaware Bay
- Pet-friendly rentals Delaware Bay
- House rentals Delaware Bay
- Family-friendly rentals Delaware Bay
- Rentals with beach access Delaware Bay
- Bungalow rentals Delaware Bay
- Townhouse rentals Delaware Bay
- Rentals with a washing machine and dryer Delaware Bay
- Rentals with breakfast Delaware Bay
- Apartment rentals Delaware Bay
- Rentals with a kayak Delaware Bay
- Smoking-friendly rentals Delaware Bay
- Cottage rentals Delaware Bay
- Rentals with outdoor seating Delaware Bay
- Fitness-friendly rentals Delaware Bay
- Rentals with pools United States