
Vacation rentals with a pool in Wellfleet
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Top-rated rentals with a pool in Wellfleet
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Wellfleet rentals with a pool
House rentals with a pool

Stunning Cape Home - Inground Pool, 5 Min To Beach
This house and property were charming and beautiful. The location was extremely close to beaches, restaurants, and stores all while being nestled in a quiet neighborhood. Highly recommend!

House on Cape Cod with pool close to beach
Alena's place had everything we needed for a lovely week on the Cape. Great pool and location between Mayflower and Dennis Village. My daughter loved the home's bright airy playroom and it kept us sane and entertained on a couple of rainy days. Would definitely visit again!

"Cape Escape" luxury home w/pool & beach access.
We have stayed in multiple houses / penthouses throughout the U.S. , however, this home surpassed them all. Jennifer was amazing from the beginning of the booking with answering my questions and went above and beyond to make this special occasion memorable. The house is well equipped! The sounds of birds chirping in the morning , the breeze, and the view of the pond when drinking coffee was so serene. The space in the house was more than I expected with everyone having lots of space to enjoy all the designated areas for playing board games, Video game room( so cool) , reading , watching tv - there was a room for everyone’s enjoyment from our 12 year old, 17, 25, to my 78 year old parents. The well thought out toiletries in every bathroom, spa slippers and robes in each bedroom, ear plugs located by the bedside, laundry room that has labeled racks of beach items and games , kitchen with all its wonderful amenities- I can do on and on. We WILL be back !

Tranquil Family Retreat in Plymouth
Overall, the home was beautiful, and my friends and I truly enjoyed our stay. The only minor challenges were getting in through the front door and not having a chance to use the arcade. The kitchen area was absolutely stunning, and I personally loved the master suite. We all agreed that we could definitely see ourselves coming back. Apologies for our late-night conversation getting a bit too lively—the gentle reminder was appreciated. Thank you for being such wonderful hosts!

Getaway with pool
We stayed here for weekend in November with multi-generations of family members. Lots of space to spread out - and the middle age group enjoyed the turn-table! Spacious kitchen, comfortable beds and clean bathrooms. Thanks!

Home in Hyannis Port
Our family of five had a wonderful stay! We picked the location because it was in the middle of the Cape and easy for us to explore the coast. The house is newly renovated and in pristine condition. The beds were comfortable and the bathrooms were fresh and new. We had plenty of space and felt right at home. The host was very responsive. We highly recommend!

Glutton's Doom: Bright & Airy East End Delight
Great location and lovely space! We loved our stay here. We were a 15-20 minute very pleasant walk to the main commerce and there’s an adorable little market right next door to the house for any groceries and baked goods. The house has everything you’d need and is surrounded by trees. Very peaceful.

Large Home Heated Swimming Pool Private Beach
We had a great stay at this place! The house was exactly as described—clean, comfortable, and well-stocked with everything we needed. Check-in was smooth, and the host provided clear instructions throughout. The neighborhood was quiet and convenient, with easy access to local attractions and restaurants. Would definitely recommend this spot to anyone visiting the area!
Condo rentals with a pool

Ocean Edge: 2 bed/2 bath - Pools & Resort Access
Had a great weekend at Josh’s place! Smooth booking process, great communication, easy checkin. The space was clean and exactly as advertised. I’d definitely recommend both Josh as a host and this location as a Cape getaway!

Stylish & Modern Studio Condo - Steps to the Beach
I had a fantastic experience during my stay! The place was exactly as described—clean, cozy, and well-equipped. The host was incredibly welcoming and responsive, making the check-in process a breeze. The location was perfect, with easy access to local attractions and restaurants. It truly felt like a home away from home. I would definitely recommend this place to anyone looking for a great stay. I can't wait to come back!

Hidden Hideaway
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.

Spectacular Waterfront Condo
What a special place to have your morning coffee, overlooking the gorgeous ocean views! The place was spotless, exactly as pictured, super clear entry and instructions. So close to all P’town has to offer but just far enough off the main strip for some real peacefulness! Would recommend to anyone! Hosts provide excellent local information and were incredibly communicative. Thank you!

A Beautiful Es-Cape
Jean Pierre provided us with a great place to stay in a location with a lot to offer. Everything was very neat and clean, and he was very responsive to any questions we had. Thanks again!

Golf Course Views and Pools
My wife and I wanted a little end of summer get away and we couldn’t have been happier choosing Alexa’s condo at Ocean Edge! The condo was beautifully decorated, very clean, and everything we could have wanted for our short vacation. Alexa was always very responsive and friendly, we’ll certainly be keeping her in mind for our next cape vacation! Highly recommend for small families and couples!

Oceanview Condo w/ Fireplace & Patio
The place was very comfortable with beautiful views of the ocean. It was off season & a bit cool so we really enjoyed the indoor heated pool & jacuzzi and walking the beach. So nice to hear the surf when falling asleep! The space was clean & comfortable and the cozy fireplace delightful on the cool nights.

6 Min to Beach - Pool - Private Balcony - Central
My boyfriend and I stayed in this beautiful and quaint condo for a wedding weekend in Dennis and it couldn’t have been a more perfect place with a more perfect location!We both felt safe and comfortable immediately upon arrival and loved spending time outside on the porch and enjoying walking around the area! We would both recommend this stay to anyone!
Quick stats about vacation rentals with a pool in Wellfleet
Total rentals
20 properties
Nightly prices starting at
G$20,980 GYD before taxes and fees
Total number of reviews
750 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Owen Park Beach
- Coast Guard Beach
- Onset Beach
- Inman Road Beach
- Nickerson State Park
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Cahoon Hollow Beach
- Peggotty Beach
- Kalmus Park Beach
- Ridgevale Beach
- Forest Beach
- Linnell Landing Beach
- White Horse Beach
- Cape Cod National Seashore