Villa Bay - Vacation Rentals in Pebble Beach

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From US $471

         

10.0 (142 Reviews)

House

WaterViews Overlooking Gloucester Inner Harbor/Sunroom/Deck/Walk to Town/AC

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $596

         

10.0 (1 Review)

House

Big New England Family Home; walk to beach, shops

• Parking
• Security/Safety
• Child Friendly

• Massachusetts
• Rockport

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From US $230

         

|

9.8 (373 Reviews)

Bed & Breakfast

Addison Choate Inn

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $245

         

10.0 (135 Reviews)

House

Romantic Summerwind Cottage, Scenic Harbor View w/Large Deck

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $270

         

|

9.8 (9 Reviews)

House

Gloucester Coastal Gem

• Balcony/Terrace
• Security/Safety
• Sports/Activities

• Massachusetts
• Gloucester

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From US $243

         

|

9.8 (283 Reviews)

Bed & Breakfast

The Seafarer Inn

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $555

         

10.0 (219 Reviews)

Cottage

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Gloucester

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From US $249

         

|

9.6 (40 Reviews)

Apartment

Ocean Breeze-8min Walk to Beach

• Air Conditioner
• Parking
• View

• Massachusetts
• Gloucester

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From US $204

         

|

9.4 (129 Reviews)

Bed & Breakfast

Sally Webster Inn

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $214

         

9.2 (126 Reviews)

House

Quaint getaway with full kitchen and lush yard - close to the beach and downtown

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Rockport

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From US $714

         

9.8 (14 Reviews)

House

Two Beaches: Long Beach & Good Harbor

• Parking
• TV
• View

• Massachusetts
• Gloucester

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From US $676

         

9.6 (10 Reviews)

House

Granite Pier: Blends craftsmanship with modern amenities. Water views!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $725

         

9.4 (12 Reviews)

House

Sage Hill: Long Beach & More!

• Air Conditioner
• Pet Friendly
• TV

• Massachusetts
• Rockport

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From US $1,688

         

10.0 (50 Reviews)

House

Spectacular, luxury waterfront property directly overlooking Sandy Bay.

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $393

         

9.2 (9 Reviews)

House

Granite Cottage: Pigeon Cove Delight

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $238

         

8.6 (41 Reviews)

Cottage

A Beautiful "WEE " Place By The Sea in Rockport

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Rockport

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From US $142

         

9.4 (98 Reviews)

Cottage

Cozy Cottage Old Fashioned Charm

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $321

         

7.6 (39 Reviews)

Cottage

Cozy oceanfront home with unique architecture

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $493

         

10.0 (165 Reviews)

Condo

'We can't wait to return to Four Winds'

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $219

         

10.0 (124 Reviews)

Cottage

Come home to Rockport!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $716

         

10.0 (74 Reviews)

House

Luxury Home in the Heart of Rockport

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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From US $312

         

10.0 (72 Reviews)

House

WALK TO BEACH! Great Location! Booking 2026! Close to Salem!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $383

         

10.0 (56 Reviews)

House

5-star home with quick walk to 2 beaches!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $949

         

10.0 (55 Reviews)

House

Beach & King - Stunning Ocean Views!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Rockport

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★ Pro Tip: Villa Bay makes it easy to compare the best listings on Villa Bay homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Villa Bay homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pebble Beach.