Vineyard Vacation Rentals

There are a lot of options in Vineyard. If you plan on staying in the Vineyard area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Vineyard:

• Gorgeous ocean views! Spend your days in pure bliss at a perfect paradise!
• LUXURY VILLA! HIGHEST GUEST RATINGS ON ISLAND! DISCOUNTED SUMMER RATES!
• Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach
• Beautiful beachfront at The Villas On Great Bay
• Luxury Villa, Walk to beach, BRAND NEW 55KW BACKUP GENERATOR
• DREAM 5-Star Premier BEACHFRONT 3 Bedroom Villa + Private Pool
• Villa Suzanne - Ocean Views
• Private Oceanfront Luxury Villa, Infinity Pool, Gym, Short Walk to Sandy Beach
• Villa Tropicale and paella party
• luxury quiet 2 bedrooms private pool breathtaking view

There are 325 vacation rentals with private pools near Vineyard. Top-rated RBO homes that have access to a swimming pool include:

• ☀️👙Sea Fan by IRE Vacations - Exquisite Villa With Views from Each Bedroom
• Océan Cave
• The Villas on Great Bay, Beachfront Villa 4
• Secluded Hillside Villa, Large secluded pool & Endless Views, Bossa Nova

If you are looking for a family-friendly vacation home in Vineyard, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Vineyard:

• Oyster Pond - Oyster Bay Beach Resort - Condo
• Luxury cozy Apartment
• Océan Cave

Currently, the total number of properties listed by Rent By Owner in 2026 is over 1023 in the Vineyard area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Vineyard. 

Cancellation policies vary depending on the property owner, so it's essential to review the specific listing details. Be sure to check the individual rental's cancellation terms before booking or contact the host directly for clarification.

Amenities offered can differ between properties, ranging from pools and Wi-Fi to kitchen facilities. To find the best fit for your stay, review the listing descriptions carefully and reach out to hosts if you have particular requirements.

You can filter search results by your preferred travel dates to view available properties. It's advisable to book early, especially during peak seasons, to ensure you secure the ideal rental for your stay here.

Many property owners are willing to accommodate special requests or upgrades; however, this depends on availability. Contact the host directly after booking to discuss any specific needs or preferences you may have.

If problems arise, promptly contact the property owner or local support team listed in your booking details. Reliable hosts typically respond quickly to resolve issues, ensuring your stay remains comfortable and enjoyable.