
Surfside long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in Surfside. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Surfside are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Surfside
Showing deals for:25 Jan - 22 Feb
Image gallery for A True Madaket Gem-Direct Water Views, Pool & Option to Add 3 Bedroom Cottage

A True Madaket Gem-Direct Water Views, Pool & Option to Add 3 Bedroom Cottage
Nantucket
Image gallery for Spacious Surfside home just a short walk to Nobadeer Beach!

Spacious Surfside home just a short walk to Nobadeer Beach!
Nantucket
Image gallery for Pond View Cottage- Luxury home near Miacomet beach

Pond View Cottage- Luxury home near Miacomet beach
Nantucket
Image gallery for 7 BR Beautiful gardens, Pool, Movie theater Walk to town Bike to Brewery & beach

7 BR Beautiful gardens, Pool, Movie theater Walk to town Bike to Brewery & beach
Nantucket
Image gallery for Luxury Surfside Home 5BR Heated Pool + Outdoor Kitchen + Fire Pit Walk to Beach

Luxury Surfside Home 5BR Heated Pool + Outdoor Kitchen + Fire Pit Walk to Beach
Nantucket
Image gallery for Secluded Nantucket Retreat: Newly Renovated Home with Deck on 2 Acres!

Secluded Nantucket Retreat: Newly Renovated Home with Deck on 2 Acres!
Nantucket
Image gallery for OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.

OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
Nantucket
Image gallery for Cute, Quiet, Comfortable, Centrally Located, Outdoor Shower, Large Yard, BBQ

Cute, Quiet, Comfortable, Centrally Located, Outdoor Shower, Large Yard, BBQ
Nantucket
Image gallery for 100 Steps to Main Street. 5 bedrooms and 6.5 baths. New and Completely renovated

100 Steps to Main Street. 5 bedrooms and 6.5 baths. New and Completely renovated
Nantucket
Image gallery for Escape to Nantucket's charm, just a 6-min drive from Surfside Beach

Escape to Nantucket's charm, just a 6-min drive from Surfside Beach
Nantucket
Image gallery for 6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!

6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!
Nantucket
Image gallery for BRIGHT and STYLISH 2BD,1BT with deck and BBQ

BRIGHT and STYLISH 2BD,1BT with deck and BBQ
Nantucket
Image gallery for Great sunsets on the beach in 3-bedroom Nantucket house with AC

Great sunsets on the beach in 3-bedroom Nantucket house with AC
Nantucket
Image gallery for Walk to Children's Beach- house w/ Yard + Firepit

Walk to Children's Beach- house w/ Yard + Firepit
Nantucket
Image gallery for Charming home tucked on a lovely lane - 10 min walk to main street

Charming home tucked on a lovely lane - 10 min walk to main street
Nantucket
Image gallery for Summer Living! Nantucket Island Home with Pool, 6 bedrooms, AC, amenities

Summer Living! Nantucket Island Home with Pool, 6 bedrooms, AC, amenities
Nantucket
Image gallery for Beautiful House Minutes from Town, on Bike Path

Beautiful House Minutes from Town, on Bike Path
Nantucket
Image gallery for Now booking for 2026!

Now booking for 2026!
Nantucket
Image gallery for Spacious 5-bedroom house in Nantucket with private pool and pet-friendly

Spacious 5-bedroom house in Nantucket with private pool and pet-friendly
Nantucket
Image gallery for Private Beach House in Surfside

Private Beach House in Surfside
Nantucket
Image gallery for Spacious Saltbox Colonial close to town and beaches

Spacious Saltbox Colonial close to town and beaches
Nantucket
Image gallery for Prime Brant Point Location – 5-Minute Walk to Beach & Downtown

Prime Brant Point Location – 5-Minute Walk to Beach & Downtown
Nantucket
Image gallery for Rebuilt Captains Home A Couple Blocks From Town Center

Rebuilt Captains Home A Couple Blocks From Town Center
Nantucket
Image gallery for Charming new renovated 3 bed/ 1 Bath condo sleeps 6+Walk & Bike to everything

Charming new renovated 3 bed/ 1 Bath condo sleeps 6+Walk & Bike to everything
Nantucket
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Surfside
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Surfside Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Surfside come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Surfside
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Surfside with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Surfside
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Surfside with flexible cancellation policies.