50 Best Gloucester Apartments on Holiday Lettings - Vacation rentals

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194 Vacation rentals

20

Gloucester Vacation apartment rental

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both …see more

from $230 / night

$1,080 - $1,777 / week

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from $230 / night

(1) Excellent 

17

Home rental in Gloucester

Cape Ann / Gloucester

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Ask about children
Welcome, cher ami ("dear friend"), to this gleaming second-floor vacation rental. Cher Ami is available as a summer rental and an off-season rental. Cher Ami is a spacious and sunny apartment, with 2 bedrooms plus an office space, an eat-in kitchen with an island, 2 …see more

from $160 / night

$1,115 - $1,215 / week

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from $160 / night

(5) Excellent 

14

Apartment rental in Gloucester

Cape Ann / Gloucester

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around …see more

from $150 / night

$1,000 - $1,900 / week

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from $150 / night

17

Vacation home rental

Cape Ann / Gloucester

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Sun when you want it. Shade when you need it. Cool Cove is a beach house vacation rental that has it all! Sitting above Wingaersheek Beach, you will feel like you can see forever, enjoying views of Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, and sa …see more

from $1,280 / night

$5,880 - $7,830 / week

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from $1,280 / night

(1) Excellent 

24

Vacation cottage in Gloucester

Cape Ann / Gloucester

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Enjoy a peaceful retreat in coastal New England by staying at 'Blue Heron Cottage' - a lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby bea …see more

from $199 / night

$1,393 - $1,813 / week

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Responds fast!
avg. 18 minutes

from $199 / night

40

Vacation home in Gloucester

Cape Ann / Gloucester

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Pet friendly
This stately Victorian home just above Gloucester’s historic harbor evokes the feel of a gracious bygone era. Elegant and spacious, the home has belonged to the same family since the 1880's and was lovingly renovated to offer modern amenities and comfort. Beachmont has …see more

from $480 / night

$2,380 - $3,080 / week

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from $480 / night

23

Vacation home in Gloucester

Cape Ann / Gloucester

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 0.2 mi
  • Child friendly
  • Air conditioning
4 Bedrooms, 3 Baths (Sleeps 8) beautiful views, steps to private coffins beach Beautiful single family beach cottage, nestled among the pine trees, located on the private side of Wingaersheek Beach, which is well known as one of the most beautiful beaches on the North …see more

from $300 / night

$21,000 / week

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Responds fast!
avg. 11 minutes

from $300 / night

11

Gloucester Vacation studio rental

Cape Ann / Gloucester

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. One block walk to Good Harbor Beach and scenic Back Shore. We call your home awa …see more

from $165 / night

$975 / week

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from $165 / night

15

Vacation home in Gloucester

Cape Ann / Gloucester

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
Located right around the corner from Gloucester’s fabled Stacy Boulevard, this completely renovated vacation rental home provides convenient access to downtown Gloucester. Gloucester Harbor and Stage Fort Park, with its beaches and playgrounds, are just a short stroll a …see more

from $325 / night

$1,605 - $1,880 / week

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from $325 / night

33

Gloucester Vacation home rental

Cape Ann / Gloucester

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Rosemarc House has stairs that take you directly onto the private portion of Good Harbor Beach. This elegant and contemporary vacation rental home is the ultimate beach getaway. Incredible 180 degree views of the whole length of the beach, Salt Island and north up the c …see more

from $1,433 / night

$10,030 - $10,116 / week

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from $1,433 / night

40

Home rental in Gloucester

Cape Ann / Gloucester

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Ask about children
Imagine a summer of bliss, swimming from the dock at high tide, or from the sandy beach at low tide, when you stay at Annisquam Singing Pines. Or easily paddle to one of the nearby islands or to Wingaersheek Beach for a day in the sand and surf. Annisquam Singing Pin …see more

from $670 / night

$3,530 - $4,380 / week

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from $670 / night

(1) Excellent 

12

Gloucester Vacation home rental

Cape Ann / Gloucester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Pet friendly
Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage h …see more

from $186 / night

$1,300 - $2,340 / week

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Responds fast!
avg. 3 hours 13 minutes

from $186 / night

17

Vacation home in Gloucester

Cape Ann / Gloucester

5 13 2 nights min

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Child friendly
**There is a possibility that construction will ongoing near the property during the summer of 2016** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two …see more

from $429 / night

$3,003 / week

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from $429 / night

(3) Very Good 

26

Vacation apartment in Gloucester

Cape Ann / Gloucester

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Private garden
UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a ve …see more

from $115 / night

$805 / week

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from $115 / night

30

Vacation home in Gloucester

Cape Ann / Gloucester

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
Enjoy the ambiance of Victorian Gloucester with all the amenities of the 21st century from this classic period vacation rental home, which is tastefully decorated with the traveler in mind. Enter the house through the front door and enjoy two parlors--one with a large b …see more

from $545 / night

$2,705 - $3,575 / week

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from $545 / night

37

Vacation home in Gloucester

Cape Ann / Gloucester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Explore one of America's oldest towns during your stay in this sleek home, featuring an upstairs deck for direct access to the Atlantic's fresh air. Central air conditioning and Netflix streaming capabilities invite visitors to unwind after a day exploring rocky shores …see more

from $99 / night

$693 / week

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Responds fast!
avg. 26 minutes

from $99 / night

24

Gloucester Vacation home rental

Cape Ann / Gloucester

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Pet friendly
This lovely beach house has it all: prime Good Harbor Beach location, views, historic charm and modern comfort and style. The original cottage was built as a stone carriage house to a neighboring estate. A wonderful octagonal addition has created a three bedroom/two ful …see more

from $640 / night

$3,180 - $4,380 / week

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from $640 / night

28

Home rental in Gloucester

Cape Ann / Gloucester

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Enjoy a coastal retreat when you stay at this one-bedroom apartment in Gloucester. Complete with stunning ocean views and a great location near several beaches, this unit has modern amenities inside, along with a lovely patio and outdoor grill. Located in Gloucester, …see more

from $57 / night

$399 / week

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Responds fast!
avg. 26 minutes

from $57 / night

27

Vacation home in Gloucester

Cape Ann / Gloucester

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Ideally situated between two of Cape Ann's most beautiful beaches, this ideal vacation rental home is a mere 3-minute walk to Long Beach and an 8-minute walk to Good Harbor Beach. The home has a single level and an open floor plan that offers convenience and practicalit …see more

from $463 / night

$1,980 - $3,080 / week

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from $463 / night

23

Gloucester Vacation home rental

Cape Ann / Gloucester

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Ask about children
Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fable …see more

from $650 / night

$3,230 - $4,330 / week

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from $650 / night

(9) Excellent 

46

Vacation apartment in Gloucester

Cape Ann / Gloucester

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Reservations from June 22 to end of September must be for 7 nights minimum with Check-in on Friday afternoon. The view is spectacular! The apartment is inside a commercial marine building so it's right on top of the water, where the ships come in to unload lobsters an …see more

from $110 / night

$840 - $1,512 / week

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Responds fast!
avg. 3 hours 13 minutes

from $110 / night

(2) Excellent 

7

Home rental in Gloucester with golf nearby

Cape Ann / Gloucester

5 11 1 night min

  • 5 bedrooms
  • Sleeps 11
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Spacious home located two blocks from Atlantic Ocean and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat in July & August. Large modern fully equipped kitchen with double oven, 5 burner Viking cooktop, dishwash …see more

from $500 / night

$3,500 / week

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Responds fast!
avg. 3 hours 20 minutes

from $500 / night

38

Vacation home in Gloucester

Cape Ann / Gloucester

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Air conditioning
Your Gloucester vacation experience awaits you in this spacious and versatile vacation home. Bell View can accommodate up to 16 people, making it the perfect getaway for family reunions or vacations with friends. The house was completely refurbished and refreshed in 201 …see more

from $970 / night

$4,830 - $6,630 / week

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from $970 / night

(1) Good 

24

Vacation studio rental

Cape Ann / Gloucester

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Ask about children
Captain John Stephens House is a stylish and sparkling, newly remodeled studio condominium unit located in the heart of Gloucester. There are 4 units in this building and Unit 3 is on the ground floor. This bright and modern studio makes a perfect summer vacation home f …see more

from $90 / night

$630 - $980 / week

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from $90 / night

18

Gloucester Vacation home rental

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true wa …see more

from $250 / night

$4,950 / week

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Responds fast!
avg. 1 hour 55 minutes

from $250 / night

29

Vacation cottage in Gloucester

Cape Ann / Gloucester

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Ask about children
Get away from it all and unwind at this comfortable riverfront vacation retreat. Located in a quiet neighborhood, Thurston Point Cottage offers a relaxing atmosphere with spectacular sunset views over the Annisquam River. You might choose to sip a cool drink on one of t …see more

from $480 / night

$2,380 - $2,505 / week

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from $480 / night

25

Gloucester Vacation apartment rental

Cape Ann / Gloucester

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Glouce …see more

from $588 / night

$2,730 - $3,680 / week

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from $588 / night

20

Home rental in Gloucester

Cape Ann / Gloucester

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly
This large and comfortable vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the ground floor the …see more

from $580 / night

$2,630 - $3,678 / week

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from $580 / night

21

Vacation home in Gloucester

Cape Ann / Gloucester

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This delightful 3 bedroom, 1.5 bath Queen Anne-style vacation rental home is bright and cheery and just waiting for you! Enter the house into the kitchen from the verdant and sizable back yard (or choose one of the other 2 doors). The sunny kitchen has plenty of stor …see more

from $330 / night

$1,280 - $1,845 / week

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from $330 / night

(17) Excellent 

26

Cottage rental in Gloucester

Cape Ann / Gloucester

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large pri …see more

from $240 / night

$1,860 - $2,000 / week

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Responds fast!
avg. 3 hours 15 minutes

from $240 / night

40

Gloucester Vacation home rental

Cape Ann / Gloucester

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
A riverfront property on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets seen from the deck or from the delightful gazebo. This home has a brand new custom kitc …see more

from $530 / night

$2,630 - $3,455 / week

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from $530 / night

21

Vacation home rental

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Pet friendly
Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic "Gloucester Fisherman at the Wheel" sculpture -- a symbol of the fishing port's rich history as a working waterfront and …see more

from $280 / night

$1,280 - $1,720 / week

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from $280 / night

19

Cottage rental in Gloucester

Cape Ann / Gloucester

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
Enjoy the views of the sparkling Annisquam River, lovely Wingaersheek Beach and the Annisqaum Yacht Club just across the river. You'll also be wowed by the incredible sunsets that await you every evening from this 3 bedroom/3.5 bath vacation rental home, which efficient …see more

from $450 / night

$2,230 - $3,030 / week

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from $450 / night

33

Vacation home in Gloucester

Cape Ann / Gloucester

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Direct waterfront on picturesque Goose Cove, this vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, …see more

from $450 / night

$2,230 - $3,080 / week

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from $450 / night

31

Vacation home rental

Cape Ann / Gloucester

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly
Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2.5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious su …see more

from $672 / night

$2,930 - $4,243 / week

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from $672 / night

11

Home accommodation in Gloucester

Cape Ann / Gloucester

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
For the adventurer, this home is a short swim away from Good Harbor Beach. Located on the edge of a scenic marsh, you can swim or paddle your rented kayak or SUP over to the beach. Enjoy the day on the sands and then either come back on the tide or cross over the foot b …see more

from $350 / night

$1,730 - $2,530 / week

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from $350 / night

(1) Excellent 

12

Apartment rental in Gloucester

Cape Ann / Gloucester

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 1 mi
Enjoy your morning coffee and breathtaking sun rises on the covered porch, listen to the birds singing before you walk to Half Moon beach for a relaxing day at the ocean. Private entrance, dedicated parking spot on premise, fully equipped kitchen (with fridge, oven, s …see more

from $125 / night

$745 / week

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from $125 / night

20

Vacation home in Gloucester

Cape Ann / Gloucester

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Ask about children
This comfortable recently renovated 3 BR vacation home is conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort Park, once a landing place for pirates, now home to two public beac …see more

from $275 / night

$1,355 - $1,780 / week

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from $275 / night

(2) Very Good 

12

Home rental in Gloucester

Cape Ann / Gloucester

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about pets
This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is …see more

from $314 / night

$2,200 / week

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Responds fast!
avg. 3 hours 18 minutes

from $314 / night

25

Gloucester Vacation home accommodation

Cape Ann / Gloucester

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
Location, location, location! Waterviews & a short walk to Good Harbor Beach. This four bedroom/2.5 bath vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so cl …see more

from $633 / night

$4,430 - $5,039 / week

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from $633 / night