Holiday rentals with a pool in Delaware

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Delaware

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

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Guest favourite

Home in Rehoboth Beach

4.99 out of 5 average rating, 127 reviews

Secluded beach beauty with private, heated pool

The LV home by architect Rocio Romero is a modern classic, we love it… The heated, salt water pool is open mid-May to mid-October. You can cook in the fully equipped kitchen and eat indoors or on the large deck out back, play in the pool or fenced yard, lie in the hammocks, play games, do puzzles... We are right by the Junction and Breakwater bike trail; it's about 2 miles to the Rehoboth Boardwalk, 6 miles to Lewes. There's high speed WiFi, a Sonos audio system, and a Roku smart tv (no cable).

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Home in Rehoboth Beach

4.75 out of 5 average rating, 8 reviews

Bluewater Beach House - "Under New Management!"

This bright comfy home is perfectly located in Rehoboth Beach. A 1 block walk to Silver Lake and a 3.5 block walk to the famous boardwalk! Stroll to the shops & restaurants of Rehoboth beach. And, best of all, the house has its own in-ground private swimming pool for relaxing at home after a long beach day. Enjoy the sun room overlooking the pool and backyard patio. Eat lunch poolside! Relax on the loungers by the pool, rinse off the sand after a great beach day and grill up dinner poolside!

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Townhouse in Bethany Beach

4.93 out of 5 average rating, 109 reviews

Lakefront slps 6; beach, pools, tennis, gym, view!

Lake front in Sea Colony Resort! Walk to beach, pools, tennis/pickleball, putting green, bocce, shuffleboard, fishing ponds, fitness center & more! 24/7 security. Completely renovated. Well equipped kitchen opens to bright, charming living/dining rooms with seating for six. AC, charcoal grill, washer/dryer, wifi, 3 flat screen TV's & 3 queen beds. Beach tram & pool across street. Large deck with great view of lake and fireplace in living room! Professionally cleaned between guests.

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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

Flat in Lewes

4.98 out of 5 average rating, 44 reviews

1 BR apartment with pool and kitchenette

2nd floor outside entrance with deck, central air, 1 queen bed, large bathroom, and kitchenette with sink, air fryer, microwave, kurig (bring your own pods), and fridge. Two car parking. The space is suited for 2 people, but there is a cot available for a third person (extra fee). This space is not suited for pets or children under 12 yrs. Close to beaches, restaurants, and shopping. Owner resides in the other side of the house. The pool is shared space with the owner and other guests.

Guest favourite

Apartment in Rehoboth Beach

4.96 out of 5 average rating, 93 reviews

Beautifully renovated 2BR 2BA Condo w/ pool!

Renovated and beautifully decorated 3rd floor condo (no elevator) with a comfortable, beachy feel! Across from the Tanger Outlets, you are close to tax free shopping, restaurants, bars and numerous activities for the kiddos! Rental includes full kitchen with stainless steel appliances, washer/dryer, updated bathrooms, all linens and access to the pool. See our 3 bedroom condo right down the hall if we’re booked or if you need a little more space: https://www.airbnb.com/h/rehobothfamilyfun

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.

Guest favourite

Townhouse in Ocean View

4.96 out of 5 average rating, 27 reviews

Relaxing Bethany Beach Retreat, Pools, Dogs OK

Welcome to your new happy place. Just steps from the bay and minutes from Bethany Beach, the home has everything you need to unwind and relax. Community has amazing amenities including indoor/outdoor pool, game room, hot tub, and fitness center. This retreat is the perfect getaway for adults (close to beaches, great restaurants, and shopping), children (board games and game room), and your furry little friends (dog-friendly beaches and trails). Perfect for families small and large!

Guest favourite

Townhouse in Rehoboth Beach

4.92 out of 5 average rating, 105 reviews

Cute Townhouse in Rehoboth

Cute Townhome Duplex located in Rehoboth Beach. A short 5 min drive to the beach or 15 minute bike ride. Located 5 minutes from downtown Rehoboth Beach and 5 minutes from downtown Dewey beach. A quick drive to the Tanger Outlets and endless restaurants. Our property is located within a private, quiet community with a large gated pool. There is a screened in private back porch to enjoy during your stay. We our located just minutes from restaurants and attractions on Coastal Highway.

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

Apartment in Rehoboth Beach

4.98 out of 5 average rating, 83 reviews

Lovely 2BR Condo - Rehoboth/ Dewey

2 bedroom, 2 bath Condo Little over 1 mile away from the BEACH Beautiful maintained condo on first level (no stairs!) and screen in porch Location –right off Route 1 -quick access to whatever your vacation needs are. Enjoy the beach and when you return enjoy one of 3 community pools! LINENS & TOWELS PROVIDED Quick WALK to Big Fish Grill, Jungle Jim’s Water park, community pools and tennis courts Quick DRIVE to Beaches, Tanger Outlets, Boardwalk and Funland!

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.