Surfside Vacation Rentals

The Surfside Road bike path is well traveled with bikers, walkers, and roller bladers. You stop along the way at a sandwich shop or outdoor cafe. Housing ranges from the older summer cottages to newer homes off the main roads.

9 properties

Surfside Guide

Surfside vacation rentals that sleep 12

Surfside

ID 18535

4 BR
3 baths
Sleeps 12

Surfside Beach Cottage with off-street parking

Distance to beach: 3/10 Surfside and 4 min. walk & 6 min. to Lifeguard/Bus to Town

5.05 reviews

OWNER SPECIAL:

Early Booking special for Summer '27, book 32 nights for $57000 and save short-term rental taxes.

Summer:

$9,275 - $12,975/wk

$44,500 - $57,000/mo

Off Season:

$1,600/night

$8,000 - $9,250/wk

Large Beach Plum Home-Private Pool, Tennis, Gym-Sleeps 12

Nantucket

ID 39530

4 BR
4 baths
Sleeps 12

Large Beach Plum Home-Private Pool, Tennis, Gym-Sleeps 12

Distance to beach: 1.7 Miles to Surfside and 4.7 Miles to Cisco

5.022 reviews

Summer:

$20,600 - $22,600/wk

Off Season:

$1,800 - $3,000/night

$7,600 - $20,600/wk

$14,000/mo

Surfside vacation rentals that sleep 10

Big-Shoe: Surfside 5 Bedroom Beach House - 2 outdoor showers

Nantucket Surfside

ID 31798

5 BR
2 baths
Sleeps 10

Big-Shoe: Surfside 5 Bedroom Beach House - 2 outdoor showers

Distance to beach: 6/10 mile to Surfside Beach, Nantucket

5.06 reviews

Summer:

$8,200/wk

Off Season:

$6,600 - $8,200/wk

Private Pool Nantucket Retreat - On The Wave Route

Walk to town and beaches

ID 41207

5 BR
4 baths
Sleeps 10

Private Pool Nantucket Retreat - On The Wave Route

Distance to beach: 1.5 mi to Surfside and 1.5 mi to Miacomet

5.011 reviews

OWNER SPECIAL:

2027 Calendar Now Open.

Summer:

$18,000 - $22,500/wk

Off Season:

$1,350 - $1,735/night

$5,850 - $18,000/wk

$43,200 - $53,568/mo

Surfside vacation rentals that sleep 9

Surfside

ID 35350

4 BR
3 baths
Sleeps 9

Spacious Home with Private Pool

Distance to beach: 1.6 mi to Surfside

5.09 reviews

Summer:

$9,375 - $15,375/wk

Off Season:

$1,000 - $2,000/night

$6,375 - $9,375/wk

Surfside vacation rentals that sleep 8

Surfside

ID 35585

4 BR
3 baths
Sleeps 8

Surfside Compound with Pool & Spa

Distance to beach: 1.9 mi to Surfside

Summer:

$16,475 - $20,575/wk

Off Season:

$2,500 - $3,200/night

$16,475 - $19,875/wk

Spacious and Sunny 3 BR. Surfside Beach Area, Central A/C

Nantucket

ID 32848

3 BR
2 baths
Sleeps 8

Spacious and Sunny 3 BR. Surfside Beach Area, Central A/C

Distance to beach: 0.7 miles to Surfside

5.09 reviews

Off Season:

$2,300 - $2,800/wk

Surfside vacation rentals that sleep 6

Surfside Retreat in Beach Plum. Pool, Tennis and Fitness!

Nantucket

ID 42225

3 BR
3 baths
Sleeps 6

Surfside Retreat in Beach Plum. Pool, Tennis and Fitness!

Distance to beach: 1.6 Surfside

Summer:

$9,900 - $10,300/wk

Off Season:

$850 - $1,000/night

$6,300 - $7,300/wk

Surfside Nantucket

ID 9468

3 BR
2 baths
Sleeps 6

Waterfront Cottage

Distance to beach: 2/10 of a mile (1000 feet )

Off Season:

$5,000/wk