Vacation rentals with a pool in Fire Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Fire Island

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

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Guest favorite

Bungalow in East Hampton

4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

Dive into the saltwater pool, set amid professionally landscaped grounds. Later, head for the multiple outside entertaining areas for a meal from the built-in outdoor grill. Round off the day with a soak in the claw foot tub in the marbled bathroom. The pool is available from May to September, and the temperature is regulated at 87 degrees. Check with the host for additional requirements. Walk to the Clearwater Beach Association's private beach, just a few blocks from the house, with a local grocery store also close. East Hamptons village is 12 minutes away, with recommended restaurants including Roudy Hall and Citta Nova.

Superhost

Guesthouse in Hempstead

4.84 out of 5 average rating, 122 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

Guest favorite

Home in Hampton Bays

4.89 out of 5 average rating, 84 reviews

Perfect Hamptons Summer Rental with Pool

Self check in to Private Entrance of this beautiful home. Long driveway and plenty of space for parking at the home. Use of pool and amenities. Host will be staying on the property with in a separate apartment. Will be around if needed, friendly and accommodating but not intrusive! Other things to note: • Pool heating: $100 per day • House is ONLY for guests on the reservation. No exceptions. • Don’t reserve the house under one guest UNLESS you are one guest. Reservation won’t get approved

Guest favorite

Home in Sag Harbor

4.9 out of 5 average rating, 182 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence and gates around pool. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 306 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).

Guest favorite

Guesthouse in Southampton

4.96 out of 5 average rating, 160 reviews

Wonderful Private Spacious Pool House

Light, open, spacious and private pool house less than 1/2 mile from the bay beach and 4 miles to ocean beaches. Close to Southampton, Sag Harbor, and Water Mill. Families love it as do our many girl getaways. Pool and deck and BBQ and umbrellas and pool toys and lounge chairs are for your exclusive enjoyment too. Enough beds to sleep 6, but we allow up to 3 additional guests for a total of 9 with an additional fee. Portable beds and linens will be provided. Can’t book just 1 weekend night.

Guest favorite

Home in East Quogue

5 out of 5 average rating, 31 reviews

Estate-Indoor & Outdoor Pools- 5k SF + Amenities

Welcome to this modern luxurious new home boasting over 5,000 sf w/ 5 BRs and 4.5 BA, situated at the end of a private cul-de-sac. This spacious home was masterfully finished and boasts an open concept with gorgeous interiors, featuring year-round heated indoor pool & hot tub, outdoor pool, chef’s kitchen, two ground floor en-suite primary bedrooms, private en suite studio apt. Basketball, ping pong, fire tables, outdoor heaters, outdoor kitchen, private fenced in yard, high end furniture

Guest favorite

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.

Superhost

Home in Westerly

4.75 out of 5 average rating, 20 reviews

Saltwater POOL and BEACH PASS

This is the perfect place to spend your summer vacation. This home features an in-ground saltwater pool and comes with a beach pass to the Wuskenau Beach only 5-8 minutes away! The home is very spacious with 2 living rooms, 3 bedrooms and 2 full bathrooms and 2 decks. The downstairs living room also has a Murphy Cabinet Bed. Guests will have to sign a separate contract with Randall Realtors. This will be emailed after the booking. Managed by: Lauren Nigrelli - Randall Realtors Compass.

Superhost

Home in Ocean Bay Park

4.89 out of 5 average rating, 56 reviews

The Pink Sandbox with Hot Tub & Pool

Beach Cottage with Hot Tub & Pool in OBP. Close to everything; ferry, beach and convenience store, Schooners & Flynns. Sparking Clean, new bedding, four bedrooms, 10 beds, 1.5 bath, sleeps 12, Central AirConditioning, BBQ, deck, outdoor shower, equipped kitchen for those who enjoy cooking or baking, washer and dryer...The house is complete with towels, bedding, beach chairs, everything you need for a fun, relaxing Fire Island vacation. Under 27 needs approval prior to booking.

Guest favorite

Home in Southampton

4.93 out of 5 average rating, 28 reviews

Newly Renovated SH Village 5bd with pool

Sol Cottage is a charming five bedroom four bathroom home with a separate guest house on the property. The house is a 5 minute drive to town and the beach. A Jeep Wrangler is available for rent through turo (inquire for details). The house has a beautiful HEATED saltwater Gunite pool and a large fenced in yard. The house has brand new wide plank floors, HVAC system, and furniture. There is a wood burning fire place in the main living space, which sets a cozy welcoming vibe.

Guest favorite

Home in East Hampton

5 out of 5 average rating, 33 reviews

Stunning Central E. Hampton Home w/ gunite pool.

EH Registry #24-65. This 2800 sq foot home boasts 10' ceilings & has been re-vamped from top to bottom. Beautiful landscaping, 44' x20' deck & a 6' privacy fence Outdoor lounge furniture & dining set. The indoor dining room seats 10. Upstairs: 4 bedrooms: All mattresses are new! Baths fully stocked. Pool closes in mid Oct. and opens mid May. Pool heat is a separate fee! NO PETS. Significant pet fee required for your non shedding well behaved dog.