Vacation rentals in Jewell Island

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Top-rated vacation rentals in Jewell Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Scarborough

4.85 out of 5 average rating, 279 reviews

Charming beach cottage

Pine Point is a beautiful sleepy village surrounded on three sides by water: peaceful salt marsh, river to the sea, and ocean, with an 8 mile long white sand beach, extensive sand bars at low tide (great for sand dollars!). It is the perfect spot for an unforgettable family vacation. The beach here is considered by many to be the best walking and activity beach in Maine, as well as spectacularly beautiful. Come experience an idyllic week at the beach in Pine Point. This beach is perfect for many reasons: great swimming, windsurfing, beach combing, extensive sandbars, fishing off the jetty. The cottage is located in a quaint and quiet neighborhood, just steps from the path to the beach. Spend your days reading and sunbathing, and fall asleep at night to the sounds of the ocean just outside your window. The house has an open layout downstairs with a light breezy feel, and cozy upstairs sleeping quarters. Beautiful back yard and great deck in the shade, front porch with hammock for afternoon snoozes, and all the amenities of home. 20 minutes from the great little city of Portland for added excitement.

Apr 22 – 29

R2,124 ZAR per night
Guest favorite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Cozy heater for spring, fan in the summer. This yurt is “glampy” inside with leather chairs, pine log bed. The Island Yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Wicked good water. Seasonal restaurants. Fire pit. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to yurt.

Nov 22 – 29

R2,356 ZAR per night
Guest favorite

Guesthouse in Portland

4.95 out of 5 average rating, 278 reviews

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

Apr 25 – 30

R3,051 ZAR per night

Popular amenities for Jewell Island vacation rentals

Other great vacation rentals in Jewell Island

Guest favorite

Cabin in Bremen

4.95 out of 5 average rating, 173 reviews

Ocean Front Cottage: Little Heaven

Sep 25 – Oct 2

R3,001 ZAR per night
Superhost

Apartment in Scarborough

4.85 out of 5 average rating, 433 reviews

Tiny Pine Point Beach Pad - comfy, cozy surf shed

Apr 13 – 20

R2,011 ZAR per night
Guest favorite

Guest suite in Portland

4.91 out of 5 average rating, 193 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

Feb 17 – 24

R1,925 ZAR per night
Guest favorite

Barn in Portland

5.0 out of 5 average rating, 378 reviews

Garrison Cove Studio

Oct 26 – Nov 2

R3,336 ZAR per night
Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 214 reviews

Cottage on Black Brook Preserve

May 30 – Jun 6

R2,396 ZAR per night
Guest favorite

Guest suite in Cumberland

4.92 out of 5 average rating, 108 reviews

Springer Park! adorable guesthouse very stylish!

Jan 22 – 29

R2,825 ZAR per night
Guest favorite

Tiny home in Durham

4.99 out of 5 average rating, 295 reviews

Crow’s Nest Tiny House at Old Crow Ranch

Jan 11 – 18

R3,205 ZAR per night
Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 194 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Apr 17 – 24

R2,155 ZAR per night
Superhost

Cottage in Harpswell

4.9 out of 5 average rating, 124 reviews

Classic Maine Cottage - dock, sauna & kayaks

Oct 1 – 8

R9,306 ZAR per night
Guest favorite

Cabin in Freeport

4.98 out of 5 average rating, 469 reviews

Cozy Cottage-Near Harbor & Park

Sep 30 – Oct 7

R3,349 ZAR per night
Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 342 reviews

Waterfront Guest House on the Maine Coast

Jan 19 – 26

R2,926 ZAR per night
Guest favorite

Guesthouse in Freeport

5.0 out of 5 average rating, 23 reviews

Mast Landing Cottage

Feb 18 – 25

R2,445 ZAR per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland
  6. Jewell Island