Penthouses North America

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Casa Dorada Penthouse

Cabo San Lucas penthouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$1,201

DEVELOPERS PENTHOUSE "There is Only One"

Cabo San Lucas penthouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$1,716

Award Winning Villa Luz- Views - steps to Downtown

Pacific Grove penthouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$341

1 Bedroom/2 bath Penthouse at Casa Dorada on Medano Beach available Jan 21-28,

Cabo San Lucas penthouse

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$653

South Beach Penthouse with Private Hot Tub Patio

Florida penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$572

Beautiful new 1 bedroom PEnt House !

Playa del Carmen penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$58

Luxury Vacations 2 bedrooms Penthouse

Puerto Plata penthouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$401

2 bedroom penthouse Grand Solmar

Cabo San Lucas penthouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$4,003

2 bedroom penthouse Grand Solmar

Cabo San Lucas penthouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$4,003

Spacious Penthouse/Apartment - Heart of Tulum

Tulum penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$263

Saramanda, Sandy Lane, St. James, Barbados

Sunset Crest villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 4 match: Rental types, Beach or lakeside relaxation, Nightlife, Fax machine

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Price per night from

$2,198

Seascape, Gibbs, St. Peter, Barbados - Beachfront

Gibbes villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 4 match: Rental types, Beach or lakeside relaxation, Nightlife, Fax machine

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Price per night from

$924

Casa Dorada Medano Beach PENTHOUSE December 9 - 16

Los Cabos penthouse

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$572

Presidential Suite Paradise Resort in Punta Cana

Punta Cana penthouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$263

PENT HOUSE PERFECT LOCATION IN MAMITAS

Playa del Carmen penthouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$172

180° Ocean View 3 Br. Penthouse

Playa del Carmen penthouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$399

2 Bedroom Crown suite All inclusive Mandatory

Puerto Plata penthouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$143

Anchorage, Sandy Lane, St. James, Barbados

Sunset Crest villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 4 match: Rental types, Beach or lakeside relaxation, Nightlife, Fax machine

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Price per night from

$949

“Beautiful, peaceful, relaxation!” My wife and I stayed at Sea Beauty last month with our son, his wife and our 14 year old grandson. Owners Cathy and Jerry Frazier met us at the door with the keys and gave us a complete walk-thru and instructions for the house. Nothing was left to be desired at Sea Beauty. It has been completely remodeled and appointed with only the best, leaving nothing to be needed. Sea Beauty is an ideal location, about 20 minutes to the shops and restaurants of George Town and 20 minutes to our favorite place on the island,Rum Point on the north side. The best part of Sea Beauty is its 300 feet of private beach with great snorkeling and swimming, and especially the hammocks under the sea grape trees,always in the shade overlooking the white sandy beach. This has to be one of the most relaxing, beautiful places anywhere! Also, it is only about 20 minutes to a full-service grocery store and five minutes to two nice restaurants, especially The Lighthouse, less than two miles away. We can't say enough about this beautiful home, renovated in the classic Cayman cottage style, and the helpfulness of Jerry and Cathy. They even supplied us with cell phones with pre-programmed phone numbers for certain services. We will certainly be returning to this beautiful paradise!

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$372

Conched Out: Beach House w/ Backyard Snorkeling + Private Pool

North Side house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$452

Cayman Dream: Rum Point Beach Bungalow with Pool for Oceanfront Living

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Cayman Dream” We rented Cayman Dream in early June of 2013. We were very happy with the house. It's exactly as the pictures show. The kitchen is very well appointed and the grounds are kept very nicely. It's located in a nice quiet area with very little traffic. Our only complaint with the house was the phone/wifi. It was out for three of the six days that we were there and even after it had been fixed we had to constantly reset while we used it. With our children back in the states, we felt really out of touch. We truly enjoyed our stay and would recommend staying there.

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$486

Sea Cove: Cayman Kai Villa w/ Private Dock & Waterfront Sun Deck for

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great vacation!” There were 4 of us - 2 couples - and the house was great! There were many activities near the house and the 7 mile area is only a drive away. The beach was great, very secluded!

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$395

Fingertip: Gorgeous Waterfront Villa in Cayman Kai w/Private Beachfront!

Rum Point house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Relaxing week at the beach” This well kept home is as nice as the pictures. For folks who like to be away from the hustle of 7 Mile Beach this location is ideal. It can be a long drive to Georgetown, but with restaurants at Kaibo, Lighthouse, and Morrit's nearby, you can spend a whole relaxing week without a lot of time behind the wheel. The property manager, Chloe, was on site to greet us when we arrived, and we received a warm Cayman welcome. Chloe helped us arrange a phone to make some necessary telephone calls and she made sure we had everything we needed. It would be nice to have a kayak or two since that is a popular activity in this area. But other than that the house and visit were perfect.

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$795

Great Escape: Serene Cove Villa in the Quiet Neighborhood of Cayman Kai with

Rum Point house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Best. Vacation. Ever. Amazing. Beautiful. Relaxing.” Great Escape is a beautiful home in the perfect location. A truly luxurious property with an amazing pool and a short walk to Rum Point Beach, which is fantastic. I can't say enough about the house, the pool, the beach, the island. It truly was a perfect vacation. Although it is a drive to the other side of the island, we preferred the relaxing, quiet and island feel of Cayman Kai. The photos of Great Escape are very accurate except honestly I think the pool is bigger than it looks in the photos. Grand Cayman Villas handled our reservation in a professional, timely and courteous manner. They answered all of my questions promptly. They provided lots of information about the island, the property, restaurants, car rentals, etc. Upon arrival there were a couple minor issues (not worth mentioning) but the Villa Manager answered my call immediately and things were taken care of within 20 minutes. The owners of the property were a pleasure to deal with as well. We received an email from them before our stay with helpful information about the property and the island. We spoke by phone and met in person briefly on arrival. They were nothing but helpful and friendly. Highly recommend Great Escape and Grand Cayman Villas. It might be a few years but we will definitely be back.

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$910

Villa Caymanas: Caribbean Villa w/ Fabulous Snorkeling, Pool, & Panoramic

Old Man Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“A perfect vacation!” The second spring time vacation we had at villa caymanas. When arriving, the view entering the front door blows me away each time I arrive. Property is well maintained and everything was super clean. Private ocean side back yard made it great for relaxing. House has everything you need and some extras. We drove most days to Rum Point Beach( 10 minute drive) to relax, great beach. Spent a few days never leaving the property as we grilled fish we bought from local fisherman at the docks. With the big group we had, the villa suited us perfectly as there was plenty of room inside and out. I liked best the privacy and location of the house, we enjoy getting away from it all and this place gave us that. Worst part about the house is saying good bye.

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$629

Luxury Beach House 2 bedrooms, Playa Turquesa Ocean Club

Bavaro apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$229

Seaview Family Penthouse, Playa Turquesa Ocean Club beachfront property

Bavaro apartment

  • 1 bedroom
  • 3 bathrooms
  • sleeps 7

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$458

Fosters House, Lower Carlton, St. James, Barbados - Beachfront

Lower Carlton villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 4 match: Rental types, Beach or lakeside relaxation, Nightlife, Fax machine

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Price per night from

$3,646

Heronetta, Sandy Lane, St. James, Barbados - Beachfront

Paynes Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 4 match: Rental types, Beach or lakeside relaxation, Nightlife, Fax machine

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Price per night from

$2,727

Hidden Cove: Family Hideaway w/Free Kayaks & Bikes, Private Pool and Dock

Rum Point house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

“Beautiful house/location...but erroneous charges from owner not” This is a truly wonderful vacation rental...beautifully decorated and well situated in the cove allowing both privacy and easy access to the ocean. We had a large group and I can easily say we all agreed it was a magical spot worth returning to...especially given the bioluminescene right in our cove which we enjoyed every night! Our other concern was access to the grocery store which turned out to be a shorter drive than expected (maybe 20 mins). All was well until we checked out and the owners slammed us with erroneous charges for missing items! We were never given an innitial inventory, yet we received a massive bill and automatic charge from the owner. They even charged us for items they admitted were missing before we arrived. It was a ridiculous ending to a wonderful trip and it left us all with a bitter taste in our mouths. If you're a strong negotiator, perhaps this rental is worth your trouble.I would certainly recommend getting an inventory pre-visit and writing into the contract that you would only be held accountable for those items listed.

1 of 4 match: Rental types, Nightlife, Fax machine, Beach or lakeside relaxation

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Price per night from

$910

by Tim M - Penthouse #3000 - Surrounded by Awesome Ocean Views! Panoramic!

Cancun penthouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

“This Penthouse Was Awesome!” I recently stayed one night here with a group of 8 friends and we had the time of our lives. Tim and his partner, Mike were very accommodating and made it extremely easy for us to get settled in. The views are breathtaking as you are truly at the highest point of view in Cancun. From the outside of the building, the hotel itself looked run down but the penthouse was nice and had plenty of room. We took a short bus ride for ten pesos a person downtown at night to party and had a blast. The beach at the hotel is beautiful and clean and the pool was enjoyable as well!

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$1,063

This Astounding Penthouse is One-of-a-Kind

Cabo San Lucas penthouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

“There is no better way to relax and enjoy Cabo” We had a great time in this penthouse. It is a perfect get-a-away location with an unbelievable view. You have the option of hanging out poolside at the resort or a more quiet time at the penthouse' terrace and jacuzzi. We can't wait to go back.

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$572

by Tim M - Penthouse #3701 - Direct Ocean Big 4BR with Awesome Views!!!

Cancun penthouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

“Amazing Location and View” My stay at condo 371 was the best ever. The condo had everything needed and was very comfortable. The view from the windows and the 2 balconies is priceless. Its nice to open the doors and windows and enjoy the ocean sounds and breeze without using the aC. The patio furniture is new and I enjoyed sleeping on the balcony under the stars a couple of nights. The property manager called me after my flight arrived to confirm and he was waiting at the desk for us so we checked right into the condo without waiting. You can see the pool from this condo which is nice if you have friends in the pool while you are on the balcony. The 2 pools were freshly painted while we were there and are very nice. Its a great feature to rent a luxury condo but also have the option to cook or pay for all inclusive. The hotel has nightly activities that you can participate without paying for all inclusive. I wish to go back to this condo year after year if it is available.

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$1,063

“Best Vacation I ever had!!!” I had the best vacation ever. It was so nice having everyone together in one place.There was eight people and there was plenty of room. The view from the condo was great and the location of the condo was to. The hotel staff was excellent so was the food and drinks.I would stay again in a heart beat. We plane to go back next year.I have been to several islands and there is not to many countries these days you can go to being a american that people treat you like royalty. Cancun is one of them.

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$1,143

“Great Vacation” I was very impressed with the penthouse. Everything was all set when we arrived in Cancun and the house was AMAZING!! There was plenty of room and very comfortable. The view was INCREDIBLE! I will choose this location each time I travel to Cancun. AMAZING!!!

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$1,063

“Its like taken out of a magazine, a place to spend the vacations you deserve!” The penthouse itself is a dream come true. The pictures embrace the lovely and beautiful place, but once you get out of the elevator it just takes your breath away. It is undeniable that Cancun was an unforgettable experience, and one of the main reasons is because of penthouse #2000. It had all the commodities needed to spend an amazing time in an amazing beach. Trying to find a place was difficult until we fell in love with this one. Tim Miller made it even easier to book it since his help was undeniably one of the best I have ever had. He was super kind and available to answer my questions and doubts. As soon as we arrive at the place Francis was waiting for us with margaritas and one of the best guacamole I have ever tried. The views were astonishing since you have perfect views both from the beach and from the lake, it made it wonderful to see the sunrise from the main bedroom and the sunset from the terrace. The penthouse was extremely clean. Both bedrooms had their own private bathrooms with comfortable beds and space to put our luggage. The pools were also clean and perfect for the sunny and hot weather. The kitchen had everything needed to cook our own meals. There were also towels available for both taking a bath and going to the beach. This place was wonderful, there are definitely no complaints about anything. The service was spectacular and the place itself is like taken out of a magazine. I cannot wait to go back to for another amazing week.

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$1,063

“Best Place in Cancun” Stayed at Tim's Penthouse #372 from 5/4/15 to 5/11/15 the views from the balcony were great. Tim was great to work with, I've used VRBO before but have never received as much information from an owner as I did from Tim. Also his housekeeper Francis was very helpful whenever we had questions. She was very nice. The condo has a lot of space and was very quiet at night. We used the transportation he recommended to get to his place, Entertainment Plus. They were always on time and the stop at the supermarket is a must. We also used them to go to Chichen Itza, well worth the $109 a person. You do not need to rent a car in Cancun, the bus system is very easy to use, $1 every time you get on the bus. I will definitely rent from Tim again when I return to Cancun.

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$731

Mayan Riviera-Playa del Carmen PH

Playacar penthouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 47 minutes

1 of 4 match: Nightlife, Beach or lakeside relaxation, Fax machine, Rental types

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Price per night from

$211

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