Led by experienced agents Annie Sylvia and Grace Bishop, Studio Stays offers a personalized approach to summer rentals on Martha’s Vineyard. Whether you’re looking for a serene up-island retreat, a classic Edgartown village home, or a waterfront escape, Annie and Grace are dedicated to helping you find the perfect match. With deep local knowledge, thoughtful guidance, and seamless service, Studio Stays takes the stress out of vacation planning — so you can focus on what matters most: enjoying your time on the island.
Explore our exclusive rental properties below.
Mill Hill Road, Edgartown, MA 02539
4 BD | 4 BA | 3,600 Sq.Ft.
Katama Farm South, Edgartown, MA 02539
3 BD | 5 BA | 3,000 Sq.Ft.
Cooke Street, Edgartown, MA 02539
4 BD | 4 BA | 2,100 Sq.Ft.
Hammett Road, Chilmark, MA 02535
4 BD | 4 BA | 2,400 Sq.Ft.
Mattakesett Way, Edgartown, MA 02539
4 BD | 3 BA
Clevelandtown Road, Edgartown, MA 02539
4 BD | 4 BA | 3,220 Sq.Ft.
Hines Point Road, Vineyard Haven, MA 02539
4 BD | 5 BA | 5,276 Sq.Ft.
Katama Road, Edgartown, MA 02539
4 BD | 4.5 BA
Hines Point, Vineyard Haven, MA 02568
4 BD | 5 BA
Yardarm Way, Chilmark, MA 02535
2 BD | 2 BA
Upper Douglas Lane, Oak Bluffs, MA 02557
3 BD | 2 BA | 1,150 Sq.Ft.
North Slope Lane, Chilmark, MA 02535
4 BD | 3.5 BA | 1,900 Sq.Ft.
North Ridge, Chilmark, MA 02535
3 BD | 2,200 Sq.Ft.
Cummings Way, Edgartown, MA 02539
5 BD | 4 BA
Pond View Drive, Oak Bluffs, MA 02557
4 BD | 3.5 BA | 2,115 Sq.Ft.
Martha's Road, Edgartown, MA 02539
3 BD | 2 BA | 1,150 Sq.Ft.
Fairway Drive, Oak Bluffs, MA 02557
3 BD | 3 BA
North Water Street, Edgartown, MA 02539
6 BD | 3.5 BA | 2,957 Sq.Ft.
South Water Street, Edgartown, MA 02539
5 BD | 6.5 BA
Call for Address
6 BD | 6.5 BA | 10,000 Sq.Ft.
Let us help you find the perfect island retreat.
Our team of rental experts know the island and have access to a vast inventory of rentals, so we can help you find a perfect match beyond what's listed on our site.
From representing sellers through a comprehensive marketing plan to representing buyers with an educated view of the current market, Peyton & Bill strive to provide the highest quality service and go beyond the expected.