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Holiday rentals with a pool in Rehoboth Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Rehoboth Beach

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

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Home in Ocean View

4.86 out of 5 average rating, 64 reviews

Quiet Beach Cottage with PRIVATE POOL

POOL OPEN thru October Unexpected oasis close to Bethany Beach, all the modern comforts, & private pool! This all-season rental includes a double fireplace, so be sure to pack your swimsuit in summer and favorite heavy books in winter. Equally perfect for family vacation or romantic getaway - the choice is yours! New & comfortable mattresses, Internet, RokuTV in Living Room, Game Room, Master Bedroom. Alexa in kitchen, RING doorbell, NEST thermostat, parking, screened porch, unique artwork

Guest favourite

Home in North Cape May

5 out of 5 average rating, 26 reviews

Pool Paradise - North Cape May

Sunny Oasis with Private Pool - Steps from the Bay! Welcome to coastal paradise in North Cape May! This inviting home offers a perfect blend of modern comfort and relaxation, an ideal getaway for families and friends seeking a sun-soaked retreat. Nestled just steps away from the bay, this home provides you with the ultimate beachside experience - a PRIVATE IN-GROUND POOL. Enjoy tranquil mornings and vibrant sunsets by the water, and easily access the sandy shores for a day of and relaxation.

Townhouse in Ocean City

4.92 out of 5 average rating, 39 reviews

Sunset Island*Beautiful TH*Perfect for Families!*

OC’s best kept secret! After a relaxing day at the beach, come home to this tastefully-decorated TH in Sunset Island – a beautiful, gated community with tons of family-friendly amenities. This spacious home sleeps 12 comfortably but retains its cozy feel. No sun? No worries :) Take the kids to the indoor pool or play a board game on the screened-in porch as you wait for the sun to come out. Or there’s always the Xbox and Pac-Man console to keep them occupied! Book your stay with us today!

Guest favourite

Apartment in Dewey Beach

4.98 out of 5 average rating, 42 reviews

Stunning 2 bedroom with pool

Beautiful 2 bedroom condo in Dewey's most desired location. This condo is located at the Residences of Light House Cove with a stunning view of the bay and marina from your private balcony. The master suite boasts a king bed with a spacious private master bath. The comfortable 2nd bedroom has a queen bed with full bath easily accessible. The open floor plan allows ample room to spread out including a well equipped kitchen. The building has elevators for easy access and private parking.

Home in Lewes

4.78 out of 5 average rating, 45 reviews

Slps 6 | Comm. Pool | PetsOK | WD | Bikes | Kayaks

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.

Flat in Ocean City

4.71 out of 5 average rating, 28 reviews

3br Waterfront Assateague Island Best View

3br/2 full bath with the best view in OC . great pool. View over the Bay, Inlet & Assat. Island. You can see the wild ponies on the beach. 2 1/2 off street parking spots. Quiet & right in the middle of the action. Beautiful Sunsets. Walk to Beach and many restaurants nearby. better Info call us 410two - 2 four137 hundred - and watch the video of the house/ or any doubt. Marcia Palmisano GoodtimesinOCcom Vacation Rentals.- please bring sheets/towels & call with questions & under 25.

Home in West Cape May

4.9 out of 5 average rating, 21 reviews

5 BdRm 3 Bath Family Home with POOL

Bring the whole family to this 5 bed 3 bath with seasonal private pool, and amazing views. Rear porches overlook Nature Conservancy where you can view meadows, birds, ocean and lighthouse. Multiple spaces for gathering. Full size eat in kitchen with all the modern amenities. Located walking distance to beach, restaurants, and shopping. This house checks off all the boxes! The solar heated POOL is open late May through Columbus Day in October! WINTER RENTALS NEGOTIABLE.

Guest favourite

Home in North Cape May

4.99 out of 5 average rating, 193 reviews

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

HEATED POOL IS CLOSED FOR THE SEASON. OPENS APRIL 10, 2025 EVERYTHING YOU NEED FOR THE PERFECT VACATION! *HOT TUB OPEN YEAR ROUND, HEATED PRIVATE SALTWATER POOL open! in huge fenced in backyard. A Coffee & Tea Bar! ALL LINENS & TOWELS PROVIDED! Minutes from the Bay & the Heart of Cape May! Close to family-friendly activities, restaurants, wineries & Cape May Ferry. A short walk or bike ride to Delaware Bay! 4 Bedrooms , 2 full baths. Home of the most amazin

Guest favourite

Home in Rehoboth Beach

4.96 out of 5 average rating, 68 reviews

Modern Home with Private Pool in Rehoboth Beach

Stunning modern home within biking or walking distance to Downtown Rehoboth. Location is key! We are just a stones throw from grocery stores, shopping, and many great restaurants! Our home features a large main house with 3 bedrooms (each with its own full bath), spacious living room, dining room, custom kitchen, a large screened porch, and heated saltwater pool. The property also includes a separate studio/4th bedroom with a powder room and outdoor shower area!

Apartment in Ocean City

4.8 out of 5 average rating, 56 reviews

Renovated Downtown Townhome W/ Pool & Shuffleboard

Update- Outdoor pool closes 9/23/24 Modern, downtown Bayside 2-level townhouse w/ large community pool. Prepare to relax and unwind in this 2-level beach house! This central location makes it very easy to walk to the beach, boardwalk, and many restaurants & shops. The kitchen is fully stocked with all your cooking needs. Enjoy the pool view from right outside your sliding door. There isn't much more you could ask for. Bath and bed linens provided.

Guest favourite

Apartment in Rehoboth Beach

4.93 out of 5 average rating, 102 reviews

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, and beach chairs. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

Guest favourite

Apartment in Ocean City

4.94 out of 5 average rating, 16 reviews

Condo with Pool in the Heart of OC

First floor family friendly condominium with pool located within walking distance to the boardwalk, beach, amusement park, mini golf, and many restaurants. It has one bedroom with 2 queen beds and a pull-out sofa in the living room. Linens, bath towels, washcloths, and beach towels are provided for your convenience. The pool is located in the middle of the beautiful courtyard. There is a patio to enjoy the sunrise or sunsets.

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Popular amenities for Rehoboth Beach rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Selbyville

5 out of 5 average rating, 5 reviews

Dogs Welcome | Fireplace l Nature Trails| Gym

Guest favourite

Home in Cape May

4.98 out of 5 average rating, 49 reviews

Cape May Modern with Heated Pool/Porch Sleeps 16!

Home in Ocean City

4.82 out of 5 average rating, 51 reviews

Amazing Large 4 Bedroom West OC Town House, Pool!

Guest favourite

Home in Salisbury

4.9 out of 5 average rating, 58 reviews

The Bury Oasis: Pool◈Hot Tub◈Master Suite◈PingPong

Guest favourite

Home in Rehoboth Beach

5 out of 5 average rating, 70 reviews

Spacious Living in Rehoboth, with a Pool

Home in Ocean City

4.74 out of 5 average rating, 19 reviews

Point Break - 4BR Beach House Private Heated Pool

Guest favourite

Home in Rehoboth Beach

5 out of 5 average rating, 45 reviews

Charming, family beach house w/ private pool

Home in Rehoboth Beach

4.75 out of 5 average rating, 4 reviews

Beautiful 4BR | Pool | Deck | Tennis | W/D

Apartment rentals with a pool

Guest favourite

Apartment in Ocean City

4.89 out of 5 average rating, 27 reviews

Sunset Tranquility - 3/2.5 Midtown-1 block Ocean

Guest favourite

Apartment in Ocean City

4.96 out of 5 average rating, 28 reviews

2BR Waterfront | 1st Floor | Patio | Pool | W/D

Guest favourite

Apartment in Ocean View

4.89 out of 5 average rating, 9 reviews

Waterfront Condo With Olympic size swimming pool

Guest favourite

Apartment in Ocean City

4.85 out of 5 average rating, 80 reviews

Ocean View Condo W/ Indoor and Outdoor Pool

Guest favourite

Apartment in Milford

5 out of 5 average rating, 11 reviews

Cozy Condo

Apartment in Ocean City

4.7 out of 5 average rating, 30 reviews

OC's Only Private Resort

Apartment in Ocean City

4.88 out of 5 average rating, 40 reviews

Family Friendly Two BR OCMD Condo Bay Side

Apartment in Rehoboth Beach

4.86 out of 5 average rating, 79 reviews

Lovely Two bedroom condo with community pool.

Quick stats about holiday rentals with a pool in Rehoboth Beach

Total rentals
510 properties
Nightly prices starting at
$14 SGD before taxes and fees
Total number of reviews
16K reviews
Family-friendly rentals
430 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
290 properties have a dedicated workspace

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