Vacation Rentals & Cottages in Southwest Harbor

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8,201 cottages

C est La Vie 1, 3 or 5 Bedrooms - Walking to

Beausejour villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private tennis court Golf course on site or within 15 min walk

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Price per night from

$1,500

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Serene Room 2

Ironshore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$75

1 Deluxe Studio Villa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$132

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$160

Anita's Apartment

Punta Cana apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$172

4 Bedroom Villa in Puerto Plata Dominican Republic

Puerto Plata villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$258

5 Bedroom Villa in Puerto Plata Dominican Republic

Puerto Plata villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$229

Spacious two bedroom condo near Golf Country Club

Brownsville townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 14 minutes

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$85

Breakfast included

Everett apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$90

Playacar, 1 minute walk to the Beach!. Home away from home!

Playa del Carmen apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$212

Reunion Resort-luxe 3BR/3BA Villa-Water Park

Reunion hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Terrific Property” Dear Stacy and Craig, What a time we had! Expecting, as many Orlando-travelers do, that the theme parks would be our only major attractions, we were so pleased to be able to add our accommodations to this list as well. The Sagers have made it absolutely impossible for their guests not to have a first-class time in their condo on the Reunion property. And what an amazing property it is! Swimming pools galore (to include my daughter and son's favorite water park with a lazy river) and my personal favorite swimming and late-afternoon beverage/snacking pool area, Seven Eagles. It is here that we were able to really let-down after an amusement park day and relax only to go home to Stacy and Craig's little slice of heaven with beds that beacon even the most restless tourists. I loved the beds! So incredibly comfy with just the perfect linens making vacationers want to stay in bed just a little longer before heading back out to Sea World; Animal Kingdom; the Magic Kingdom, and the the like (all of which are not more than 15 minutes away). A true place of luxury, the Reunion four star hotel is always available to the Sager's guests serving up pub and kid fare all day and night; fine dining; and late night cocktails and sushi on the 11th floor where fireworks from local theme parks are a daily occurrence. Will we go back, yes! In fact, we have already booked again with the Sagers so we can dream away some of those cold winter days and nights looking forward to our next tip down. Thanks to you both for a wonderful stay. Jen and Dan Smith

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$205

Regal Palms 539 La Mirage Sreet

Davenport condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$229

Beautiful 2 Bedroom Modern Apartment Near NYC

Bogota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$182

RIGHT ON THE BEACH !!!!! VILLAS CHIARA PUNTA OCEANFRONT 3 BEDR GROUNDFLOOR

Bavaro apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$297

DISNEY WORLD SWEETWATER CLUB CONDOMINIUM

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great vacation stay!!!!” EVERYTHING was above what I expected! The condo was very nice and comfortable I couldn't have stayed in a better area I give this vacation home a 10 all around! I will stay here again and again if/when I visit Florida again!!! THANKS MANNY

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$75

Millennium Park Trincity Vacation Home

Trincity house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 48 minutes

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$98

Fantastic Great Value Property Nr Montego Bay

St James, Montego Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$65

New Kingston luxury suites

Kingston apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$98

Beautiful 11 pax Budget Pool Villa

Playa del Carmen b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$240

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$127

Beautiful OceanView 2B/2B Apt. 101A

Boca Chica hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 0 minutes

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$149

4 bdrm/4 bath Golf Villa incl 10 rounds of golf

Cabo San Lucas villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$1,473

Superbowl 50; February 3-10

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$573

SuperBowl house for rent

Palo Alto house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$11,450

Hammond's Ferry river front Masters Rental

North Augusta townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$916

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

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Price per night from

$115

Please see this property review on VRBO find listing ID 3942544ha

Fort Worth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$207

Florida villa

ChampionsGate villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 35 minutes

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$187

2 room PgaVillageResort by AmericanVacationLiving

Port Saint Lucie condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$455

7 Room PgaVillageResort by AmericanVacationLiving

Port Saint Lucie condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$539

7 Room PgaVillageResort by AmericanVacationLiving

Port Saint Lucie condo

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$882

5 room TampaGolfVillas by AmericanVacationLiving

Tampa condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$340

Julielm House, Worthing. Luxury Villa with private pool.

Worthing villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 23 minutes

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$409

Keyvilla-The Disney Retreat. Free Spa Heat!

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$187

DISNEY DREAM LUXURY HOME PRIVATE WATERPARK POOL SPA

Kissimmee house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

“Perfect- it was better than what we had imagined.” The communication with the owner was what really surprised me. He was very responsive to all of my questions prior to our arrival. The house was very clean and in a great location. We were 15 minutes from Magic Kingdom and had many stores around the location of the house. I would not doubt to referred this home to anyone looking to spend a weekend in Orlando. We will definitely visit again!

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$457

Sweeping Ocean Views; Private High End Condo!

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$259

Fox Run -- Sleeps 10 - 12, Only 1 mile from Okemo Jackson Gore Base

Ludlow townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$458

Miami Beach! Beautifull bay view 15th for 4 guests

North Bay Village apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 27 minutes

1 of 2 match: Private tennis court, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$171

Viewing 38 of 8,201
rentals in Southwest Harbor

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