First Encounter Beach Holiday Rentals

Compare Villas, Resorts, & Rentals in First Encounter Beach, Eastham, Massachusetts, USA

Waterfront Cottage - Adorable & Private
10.0 (82 Reviews)
1 Bedroom 2 Guests
Sunroom Mins to Beaches Views of Marsh
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10.0 (4 Reviews)
4 Bedrooms 8 Guests
Whalewalk Inn and Spa
FromR6,130 per night
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10.0 (92 Reviews)
1 Bedroom 2 Guests
Seaside Retreat w Private Beach Landing
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10.0 (4 Reviews)
3 Bedrooms 6 Guests
The Parsonage Inn
FromR3,997 per night
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9.8 (35 Reviews)
1 Bedroom 2 Guests
Waterfront, Modern, On a Pond for Boating and Swimming
10.0 (2 Reviews)
2 Bedrooms 5 Guests
The Parsonage
FromR6,257 per night
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10.0 (4 Reviews)
10 Bedrooms 22 Guests
The Inn at the Oaks
FromR4,351 per night
9.2 (322 Reviews)
1 Bedroom 2 Guests
Waterside Eastham Cottage with Quintessential Cape Cod Charm
10.0 (1 Review)
2 Bedrooms 4 Guests
Beach Getaway with Private Backyard
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10.0 (2 Reviews)
4 Bedrooms 10 Guests
4-5 Min to Mill Pond or Nauset Beach
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10.0 (2 Reviews)
4 Bedrooms 9 Guests
New 2026 3BD Home With Guest House
New
4 Bedrooms 8 Guests
Lovely House 5 Min to Beach with Deck Grill and Garage
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10.0 (2 Reviews)
4 Bedrooms 8 Guests
Dog Friend Waterfront Home
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
Truly Wonderful Cape Cottage
10.0 (135 Reviews)
1 Bedroom 2 Guests
Waterfront Fun at this Huge Family Estate
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10.0 (1 Review)
11 Bedrooms 23 Guests
Walk to Campground Beach Modern, Well‑Kept Cottage
10.0 (51 Reviews)
2 Bedrooms 4 Guests
Ocean Views New A C Dog Welcome
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10.0 (1 Review)
5 Bedrooms 11 Guests
Gorgeous Architectural Home w Water Views
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10.0 (1 Review)
4 Bedrooms 8 Guests
1 min drive to Rock Harbor, 2 min to Town!
10.0 (41 Reviews)
2 Bedrooms 5 Guests
Walk to Water Hot Tub & Game Room
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10.0 (1 Review)
5 Bedrooms 10 Guests
Great Waterfront Property, Kayak the National Park Seashore
10.0 (37 Reviews)
2 Bedrooms 6 Guests
Waterfront home with Hot Tub Firepit and Game Room
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10.0 (1 Review)
4 Bedrooms 8 Guests
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
10.0 (28 Reviews)
2 Bedrooms 4 Guests
3000 Sq Ft Home with Hot Tub
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10.0 (1 Review)
3 Bedrooms 8 Guests
The Breeze on Minister's Pond
10.0 (26 Reviews)
1 Bedroom 2 Guests
3 Bicycles Provided! Cape Cod Cottage w/Deck
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10.0 (1 Review)
3 Bedrooms 6 Guests
The Pet-Friendly Surf Shack Hideaway on the Cove
10.0 (23 Reviews)
2 Bedrooms 7 Guests
Minutes to Private Association
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10.0 (1 Review)
4 Bedrooms 8 Guests
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
10.0 (20 Reviews)
2 Bedrooms 5 Guests
Newly updated spacious steps to water
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10.0 (1 Review)
2 Bedrooms 4 Guests
New Eastham Oceanside Guest Suite with Pool and Hot Tub
10.0 (20 Reviews)
1 Bedroom 2 Guests
2 Miles to Nauset & Coast Guard Beach Dog Friendly
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10.0 (1 Review)
6 Bedrooms 12 Guests
Cape Cod Sunscape. Orleans
10.0 (17 Reviews)
2 Bedrooms 6 Guests
Half Mile to Private Association Beach
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10.0 (1 Review)
2 Bedrooms 5 Guests
Cape Cod Cottage Retreat
10.0 (15 Reviews)
2 Bedrooms 4 Guests
Steps to Rock Harbor, Fully Renovated Cape Cod Cottage
10.0 (9 Reviews)
2 Bedrooms 6 Guests
National Seashore/Updated/Game Room~Blue Pearl
10.0 (9 Reviews)
2 Bedrooms 6 Guests
1940s Cottage Stunner Large Studio w/loft feel dog friendly
9.8 (23 Reviews)
1 Bedroom 3 Guests
Beach & Golf Hub w/All-Season Sunroom in Cape Cod
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10.0 (1 Review)
5 Bedrooms 9 Guests
The Seagrove Suites & Guest Rooms
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9.2 (128 Reviews)
1 Bedroom 2 Guests
Castaway Cottage on the bay~Dog Friendly Too!
9.8 (16 Reviews)
2 Bedrooms 5 Guests
Minutes to Oceanside Beaches
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9.8 (13 Reviews)
3 Bedrooms 6 Guests
Eagle Wing Inn - Cape Cod
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9.8 (441 Reviews)
1 Bedroom 2 Guests
🐚The Bay Cottage on Thumpertown Beach
9.8 (12 Reviews)
2 Bedrooms 4 Guests
The Tranquil Heron Cottage
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9.8 (5 Reviews)
3 Bedrooms 6 Guests
Olde Tavern Motel And Inn
9.4 (253 Reviews)
1 Bedroom 2 Guests
Cozy Cottage Overlooking Rock Harbor Creek
9.8 (10 Reviews)
1 Bedroom 4 Guests
Inn at the Oaks
FromR6,336 per night
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9.7 (34 Reviews)
13 Bedrooms 31 Guests
4 Bedroom Home by Leavetown Vacations
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9.7 (3 Reviews)
4 Bedrooms 8 Guests
Private Road - Near Bike Trail & Beaches
9.6 (35 Reviews)
2 Bedrooms 4 Guests
Bike to Nauset Beach or Walk to Mill Pond
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9.5 (11 Reviews)
3 Bedrooms 6 Guests
Walk to Campground Beach Modern, Well‑Kept Cottage
9.6 (30 Reviews)
2 Bedrooms 4 Guests
Beachfront on Cape Cod Bay in Eastham! (1039)
9.6 (24 Reviews)
2 Bedrooms 6 Guests
Four Season Modern Cape Cod Cottage (with heat)
9.4 (6 Reviews)
2 Bedrooms 4 Guests
Clean and Quiet North Eastham Cottage Near Beaches
9.6 (20 Reviews)
3 Bedrooms 6 Guests
Perfect Relaxation Spot 5 min to Beach
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9.4 (5 Reviews)
3 Bedrooms 8 Guests
Waterfront amazing views near beaches
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9.3 (3 Reviews)
3 Bedrooms 6 Guests
🐳 The Whale Song - Dog-Friendly Studio
9.6 (14 Reviews)
1 Bedroom 2 Guests
Steps to Skaket Beach
FromR14,655 per night
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9.0 (3 Reviews)
4 Bedrooms 8 Guests
Newly Renovated Cottage on Town Cove!
9.6 (10 Reviews)
2 Bedrooms 4 Guests
Gray Gables
FromR10,886 per night
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9.0 (3 Reviews)
4 Bedrooms 6 Guests

About Casai's Private Villas and Holiday Rentals in First Encounter Beach

Discover more than 992 vacation rentals available in First Encounter Beach. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in First Encounter Beach.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in First Encounter Beach, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near First Encounter Beach. On average, places to stay near First Encounter Beach offer 1165.22 ft², with nightly prices averaging R10,150.

With Casai, finding and comparing holiday rentals in First Encounter Beach is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About First Encounter Beach?

What are the top holiday rentals in First Encounter Beach?

How many Casai.co.za holiday rentals are available in First Encounter Beach?

As of 2026, Casai boasts over 992 properties listed in the First Encounter Beach area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in First Encounter Beach.

Nearby Neighborhood (4)

NeighborhoodProperty Count
West Brewster Vacation Rentals in Eastham, Massachusetts 595
Pleasant Point Vacation Rentals in Eastham, Massachusetts 705
Indian Neck Heights Vacation Rentals in Eastham, Massachusetts 688
Sea Pines Vacation Rentals in Eastham, Massachusetts 750