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Vacation rentals with a pool in Stamford

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Stamford

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

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Guesthouse in Hempstead

4.83 out of 5 average rating, 127 reviews

Private Guest house with pool access.

Warning‼️this listing price is for 1 adult only. A $50 daily fee will apply for additional guest. Unapproved guest will result in cancellation no refund. Clean, stylist, peaceful, private space. Seasonal Pool access from July until 1st of September . ⛔️ Do not flush toilet paper on the toilet it will overflow, garbage disposal and trash bags are available. For pets a fee will apply. No smoking 🚭, No parties, 2 guest Max. Security Cameras. No parking on premises. Street parkings are available 24/7

Guesthouse in Southbury

4.94 out of 5 average rating, 309 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Home in West Milford

4.98 out of 5 average rating, 131 reviews

On The Rocks In The Hot Tub

Unique home featuring a large deck with an enclosed hot tub, indoor/outdoor bars, game room and seasonal pool (pool is not heated) Fall-Winter:Minutes away from the town of Warwick. Pennings, Heaven Hill Farm for apple-pumpkin picking, Peter Mountain, Mountain Creek for skiing. Many vineyards/cideries Summer: Boating on Greenwood Lake, kayak rentals, hiking (Appalachian Trail), drive-in theater, family activities at Wawanique State Park, Crystal Springs Golf and ice cream at Bellvale Creamery

Home in Monroe

4.96 out of 5 average rating, 111 reviews

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

Home in East Quogue

4.92 out of 5 average rating, 12 reviews

Private Hamptons Escape with Large Pool & Hot Tub

NEW listing from experienced 5 STAR HOST. Nestled in East Quouge, a stunning Victorian sitting on over 1.5 private acres with a 20x40 inground pool & 6 person hot tub in the spacious backyard. This 4 bedroom, 4 full bath is over 4000 Sq Ft, has addtional sleeping spaces, and play area for your younger ones. Gorgeous fully stocked kitchen and a 10 person dining space, as well as 8 person outdoor teak dining set, make this house great for gathering and entertaining your close friends and family.

Home in Bethlehem

5 out of 5 average rating, 34 reviews

Lakeview Expanse

This is a renovated house situated on 14 acres in Litchfield County, CT. This is a 5 bedroom estate - 1 king size bed, 3 queen beds, 1 bedroom is a dedicated office with a queen size air mattress. 8 guests maximum. Heated saltwater pool (closed until May 2025), 5 seater/1 lounger hot tub, 2 outdoor dining area (one on deck, other on pool patio), 8 seater dining table, 4 seater breakfast table in kitchen, extra large jacuzzi in primary bathroom, wood burning fireplace. Completely private

Home in Mastic Beach

4.93 out of 5 average rating, 118 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

Home in Bellport

4.95 out of 5 average rating, 37 reviews

Gorgeous Bellport Village Getaway with Heated Pool

A very special and warm vacation home in historic Bellport Village with 3-4 spacious bedrooms, well-appointed living spaces, beautifully-maintained garden and grounds and a wonderful heated saltwater pool. Great for weddings and other life events. Minutes from village, marina and playground at the water's edge. Perfect for a family getaway from the city. Perfect for people who love to cook. We promise you a clean, lovely home with all of the comforts for a pleasurable stay.

Rental unit in Deer Park

4.82 out of 5 average rating, 11 reviews

Serene one bedroom retreat w/ backyard oasis

**Welcome to Your Private Oasis!** Enjoy a serene escape at our cozy one-bedroom retreat. Highlights include: - **Above-Ground Pool**: Perfect for refreshing dips. - **Outdoor Patio with Gazebo**: Ideal for relaxing and unwinding. - **Private Daybed**: Your perfect spot for lounging in peace. Experience the tranquility and privacy of our oasis while being close to local attractions. Book your stay today for a relaxing getaway! Pool is seasonal until October 1st.

Home in Westhampton Beach

4.92 out of 5 average rating, 143 reviews

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

Home in Westhampton Beach

4.98 out of 5 average rating, 117 reviews

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

Home in Goshen

4.86 out of 5 average rating, 7 reviews

Beautiful home with heated pool

Escape to this spacious 4,700 sq. ft. retreat on 3 private acres, perfect for family gatherings or group getaways. With 5 bedrooms and 3.5 bathrooms, this home offers ample space and natural light from expansive windows. Enjoy the walkout basement complete with a billiard room, wet bar, and direct access to a heated pool for ultimate relaxation. Experience the best of comfort and privacy in this serene setting – your ideal escape awaits!

Vacation rentals for every style

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Apartments

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Popular amenities for Stamford rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Woodbury

4.94 out of 5 average rating, 18 reviews

Beautiful Litchfield - 2 homes in one

Home in Massapequa

4.92 out of 5 average rating, 118 reviews

Great Family Times in this 5 Bedroom House

Home in Warwick

4.98 out of 5 average rating, 56 reviews

4 bedroom house with pool (Kids & Dog Friendly)

Home in Cheshire

5 out of 5 average rating, 128 reviews

Pool House

Home in Newburgh

4.85 out of 5 average rating, 52 reviews

Entire Home (private pool), Event Friendly

Home in Ossining

5 out of 5 average rating, 14 reviews

Pool/HotTub - Close to NYC

Home in Lagrangeville

4.84 out of 5 average rating, 133 reviews

Classic Hudson Valley Farmhouse Nestled in 9 Rolling Acres

Home in Holbrook

4.97 out of 5 average rating, 33 reviews

Home for the Holidays

Condo rentals with a pool

Condo in Cherry Grove

5 out of 5 average rating, 3 reviews

Cherry Grove 1 bedroom condo w/heated pool!

Condo in Weehawken

4.33 out of 5 average rating, 9 reviews

Lovely 2 bedroom Entire Home Across Time Square

Condo in Mount Sinai

5 out of 5 average rating, 30 reviews

1856 Trading House close to water

Condo in Fishkill

5 out of 5 average rating, 5 reviews

Fishkill Living

Condo in Danbury

4.71 out of 5 average rating, 17 reviews

Quaint spacious unit, A+ location

Quick stats about vacation rentals with a pool in Stamford

Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
590 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace

Destinations to explore