Windsor Beach Holiday Rentals

      Highly Rated

Cottage

Pool House Studio In A Garden Setting + EV chargers

• Bermuda
• ·
• Smith's
• 0.69 mi to center

10.0

Exceptional

(134 Reviews)

1 Bedroom 1 Bath 2 Guests 280 ft²

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

CA $298/Night 7 Nights - CA $2,086

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Apartment

Neston

• Hamilton Parish
• ·
• Crawl Hill
• 0.36 mi to center

9.4

Exceptional

(20 Reviews)

2 Bedrooms 2 Baths 4 Guests 904.17 ft²

• 
  Oceanfront
• 
  Breakfast
• 
  Parking
• 
  Pool

CA $576/Night 7 Nights - CA $4,032

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      Price Dropped

Hotel

The Loren at Pink Beach

• Bermuda
• ·
• Smith's
• 1.13 mi to center

9.6

Exceptional

(289 Reviews)

1 Bath

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  Spa

CA $1,498/Night 7 Nights - CA $10,484

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      Highly Rated

Apartment

Water Front property with great views, pool, use of Kayaks, & strong Wi-Fi.

• Bermuda
• ·
• Hamilton Parish
• 0.49 mi to center

10.0

Exceptional

(117 Reviews)

1 Bedroom 1 Bath 2 Guests 450 ft²

• 
  Private Pool
• 
  Oceanfront
• 
  Parking
• 
  Pool

CA $467/Night 7 Nights - CA $3,272

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Resort

Grotto Bay Beach Resort

• Bermuda
• ·
• Hamilton Parish
• 1.14 mi to center

8.5

Fabulous

(97 Reviews)

8 Baths 24 Guests 355.21 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Hot Tub
• 
  Breakfast

CA $1,656/Night 7 Nights - CA $11,595

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      Highly Rated

Resort

Rosewood Bermuda

• Bermuda
• ·
• Hamilton Parish
• 1.28 mi to center

9.4

Exceptional

(523 Reviews)

1 Bath

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  Spa

CA $2,733/Night 7 Nights - CA $19,132

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      Highly Rated

Apartment

Las Brisas apartment with pool and walk to beach + EV chargers

• Bermuda
• ·
• Smith's
• 0.68 mi to center

10.0

Exceptional

(85 Reviews)

1 Bedroom 1 Bath 2 Guests 280 ft²

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

CA $275/Night 7 Nights - CA $1,924

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Resort

Rosewood Bermuda

• Bermuda
• ·
• Hamilton Parish
• 1.28 mi to center

11 Baths 37 Guests 1013.96 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Breakfast
• 
  Parking

CA $2,583/Night 7 Nights - CA $18,082

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      Highly Rated

Resort

Grotto Bay Beach Resort

• Bermuda
• ·
• Hamilton Parish
• 1.09 mi to center

9.0

Exceptional

(1013 Reviews)

1 Bath

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  Spa

CA $751/Night 7 Nights - CA $5,255

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Apartment

“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”

• Hamilton Parish
• ·
• Crawl Hill
• 0.38 mi to center

10.0

Exceptional

(33 Reviews)

2 Bedrooms 2 Baths 4 Guests

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

CA $708/Night 7 Nights - CA $4,954

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Villa

Coral Sea private beachfront panorama with infinity pool

• Bermuda
• ·
• Hamilton Parish
• 1.40 mi to center

5 Bedrooms 6 Baths 10 Guests 3003.13 ft²

• 
  Oceanfront
• 
  Breakfast
• 
  Parking
• 
  Pool

CA $3,451/Night 7 Nights - CA $24,157

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House

Extraordinary Bermuda retreat w/large cave, panoramic pool and viewing deck.

• Bermuda
• ·
• Hamilton Parish
• 0.86 mi to center

10.0

Exceptional

(18 Reviews)

8 Bedrooms 7 Baths 16 Guests

• 
  Private Pool
• 
  Oceanfront
• 
  Hot Tub
• 
  Parking

CA $8,994/Night 7 Nights - CA $62,959

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Villa

Sound Winds private oceanfront estate with private tennis court & swim dock Property overview

• Bermuda
• ·
• Smith's
• 1.23 mi to center

4 Bedrooms 4 Baths 9 Guests 3003.13 ft²

• 
  Oceanfront
• 
  Breakfast
• 
  Parking
• 
  Pool

CA $1,877/Night 7 Nights - CA $13,142

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Apartment

"Chan Mar" Tucker's Town Bermuda

• St. George's
• ·
• Tucker's Town
• 0.35 mi to center

10.0

Exceptional

(17 Reviews)

1 Bedroom 1 Bath 2 Guests

• 
  Oceanfront
• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace

CA $780/Night 7 Nights - CA $5,457

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      Price Dropped

Cottage

The Boathouse: Large Waterfront Cottage on Harrington Sound – Sleeps 4+

• Bermuda
• ·
• Smith's
• 0.44 mi to center

10.0

Exceptional

(17 Reviews)

1 Bedroom 2 Baths 6 Guests

• 
  Oceanfront
• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace

CA $576/Night 7 Nights - CA $4,032

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Cottage

2 Units Combined - Include private dock and Lovely Water Views

• Bermuda
• ·
• Smith's
• 0.31 mi to center

10.0

Exceptional

(13 Reviews)

5 Bedrooms 5 Baths 18 Guests 3000 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Ocean View

CA $2,305/Night 7 Nights - CA $16,131

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House

Unique Bermuda retreat with large cave & panoramic pool nestled into hillside

• Bermuda
• ·
• Hamilton Parish
• 0.86 mi to center

10.0

Exceptional

(11 Reviews)

5 Bedrooms 4 Baths 9 Guests

• 
  Private Pool
• 
  Oceanfront
• 
  Hot Tub
• 
  Parking

CA $6,258/Night 7 Nights - CA $43,809

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      Price Dropped

Villa

Coral Sea Oasis with private beach and infinity Pool

• Bermuda
• ·
• Hamilton Parish
• 1.40 mi to center

10.0

Exceptional

(11 Reviews)

5 Bedrooms 5 Baths 9 Guests 5000 ft²

• 
  Parking
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

CA $5,540/Night 7 Nights - CA $38,780

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Cottage

Cozy Gombey Cottage

• Hamilton Parish
• ·
• Crawl Hill
• 0.27 mi to center

10.0

Exceptional

(9 Reviews)

1 Bedroom 1 Bath 2 Guests

• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

CA $299/Night 7 Nights - CA $2,094

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House

A spacious, unique Bermuda haven with access to large crystal swimming caves.

• Bermuda
• ·
• Hamilton Parish
• 0.86 mi to center

10.0

Exceptional

(7 Reviews)

3 Bedrooms 2 Baths 6 Guests

• 
  Oceanfront
• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace

CA $2,672/Night 7 Nights - CA $18,703

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House

Waterfront Modern/Rustic Chic Retreat with Resort-style Pool and Sauna

• Bermuda
• ·
• Smith's
• 0.93 mi to center

10.0

Exceptional

(6 Reviews)

4 Bedrooms 1 Bath 8 Guests 4000 ft²

• 
  Private Pool
• 
  Oceanfront
• 
  Parking
• 
  Pool

CA $3,408/Night 7 Nights - CA $23,859

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House

Spacious Hilltop Retreat in Tuckerstown with Stunning Views, Newly Renovated

• Bermuda
• ·
• Hamilton Parish
• 1.31 mi to center

10.0

Exceptional

(4 Reviews)

4 Bedrooms 5 Baths 8 Guests

• 
  Private Pool
• 
  Hot Tub
• 
  Parking
• 
  Pool

CA $5,971/Night 7 Nights - CA $41,793

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House

Perfect Location with Water Views & Private Dock

• Bermuda
• ·
• Smith's
• 0.31 mi to center

10.0

Exceptional

(4 Reviews)

2 Bedrooms 1 Bath 8 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

CA $804/Night 7 Nights - CA $5,628

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House

CLASSIC Bermuda Home in Peaceful Smith’s Parish - STUNNING views!

• Bermuda
• ·
• Smith's
• 0.33 mi to center

10.0

Exceptional

(3 Reviews)

3 Bedrooms 2 Baths 6 Guests 1525 ft²

• 
  Oceanfront
• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace

CA $503/Night 7 Nights - CA $3,524

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