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Osa Peninsula Holiday Vacation with Pools

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    Travellers to Osa Peninsula are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    28 Matching Rentals in Osa PeninsulaView all 96 rentals
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    Cabo Matapalo Beach House  - 'Casa Verda'1 / 34
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Modern & Stylish Casa Bella Beach house *dipping pool under construction*1 / 26
    (20)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Casa Golfito with large private Pool1 / 20
    (7)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Casa Manglar, Puerto Jimenez, OSA Peninsula1 / 55
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Patio
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 7, 2018
    My 2 brothers and I returned to Puerto Jimenez after living there over 38 years ago. We were looking for a place that was authentic for the area and comfortable. We definitely...
    Reviewed August 23, 2015
    This was my wife's and my fourth visit to Costa Rica and when my brother and sisters found out what we have been up to for our vacations they requested to join us. In our search...
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    About this property
    Casa Manglar is a beautiful tropical home with 4 bedrooms each with A/C. It offers both a master and junior suite each with cable TV, walk in closets and private bathrooms. These suites are gems in Puerto Jimenez. Casa Manglar is the old family home of the owners of the resort 'La Chosa del...
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    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Star Jungle Exp. - New Home, Private Pool, Beach1 / 17
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Washer
    • Outdoor Dining Area
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 29, 2018
    This house blends eco tourism with simple luxury. A beautiful setting and experience. We were 2 couples with 2 adult children for a total of 6. A perfect place to unplug, you...
    Reviewed April 16, 2018
    Casa Jungua is one of the most special places we have ever stayed. The photos don’t do justice to the views and surrounding forest. It’s the best feeling in the world sitting on...
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    About this property
    Casa Jungua (recently completed) was built by a master timber framer and everything about it screams QUALITY. It is sustainably built and has an extremely low impact on the environment. The house is exclusively solar powered yet features many amenities one would expect from a “wired” home. Casa...
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    Cabo Matapalo, Osa Peninsula 00000
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beachfront Villa with Large Pool1 / 16
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Playa Sombrero has an open construction style that allows for a steady ocean breeze throughout the living space and provides both ocean and lush mountain views. Upstairs has a large floor plan with a beautiful hardwood floor and a thatched-roof ceiling. This room provides two netted,...
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    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Children's Pool
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From the base of our mountain, Ojochal is just a 20 minute drive north of Osa Mountain Village/Toucan Valley. Rather than suffer through the hot temperatures at sea level, you can stay at 2,000 ft. in elevation up on our mountain, with temps normally 10-15 degrees cooler. We rarely use A/C up...
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    Location Information
    Drake Bay, Osa Peninsula 12345
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Toucan Hut is the junior suite at Casa Manglar Guest House. It's aptly named because many days of the year one may view Toucans from the windows of the room. Double bed with A/C, En-Suite Bath and full walk-in Closet and Wifi and access to 2 swimming pools on the property. The house is...
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    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Entire Chosa del Manglar Nature Retreat, Puerto Jimenez OSA Peninsula1 / 127
    (1)Excellent
    10 Bedrooms, 12 Bathrooms, Sleeps 30 Quick View
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    • Air Conditioning
    • Washer
    • Housekeeping Included
    • Patio
    • Grill
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At 'La Chosa del Manglar Nature Retreat' you are GUARANTEED to see WILDLIFE. How certain are we? Well, have you ever sat around a Tropical Lounge & Bar and watched Scarlet Macaws, Monkeys or Kinkajous hang out in there natural environment? You can at 'La Chosa'. Many guests have told us that they...
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    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 10 Bedrooms, 12 Bathrooms, Sleeps 30
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    Mangrove Cabins at La Chosa del Manglar Nature Resort1 / 29
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Housekeeping Included
    • Parking
    • Waterfront
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Porch
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled into the rear gardens of La Chosa del Manglar Nature Resort sit two tropical cabins each sleeping two guests. One double or queen bed, private bathroom, slate floors & shower unit, large screened windows & overhead fans combine to create a completely authentic tropical experience. The...
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    Location Information
    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Porch
    • Wi-Fi
    • Patio
    • Balcony
    • Mountain Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You are renting the Lapa Hut at 'La Chosa del Manglar Resort'. It sleeps up to 6 individuals, 2 in a double bed and the other four in 2 bunkbeds. The Lapa Hut is large and comfortable making it great for longer stays. It offers A/C, an internal privacy wall, and an extra large bathroom. Guests get...
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    Puerto Jimenez, Osa Peninsula 60702
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Balcony
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Kinkajou Hut is the biggest suite at Casa Manglar Guest House. It's very private offering views to a private garden visited by Kinkajous, Toucans, Scarlet Macaws & White Faced Capuchin Monkeys. A King size bed awaits you as does a walk-in closet with enough room for the most demanding traveler....
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    Location Information
    Puerto Jimenez, Osa Peninsula 60702
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Mountain Views
    • Grill
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Monkey Hut is a 2 bedroom Suite at Casa Manglar Guest House with a private bathroom and hot water shower. The bathroom is not located in the guest rooms but rather adjacent. Casa Manglar is a stunning TROPICAL GUEST HOUSE. All guests at the four bedroom guest house have access to a well equipped...
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    Location Information
    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The WHALE RESORT Puerto Jimenez Osa Peninsula1 / 58
    (9)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Air Conditioning
    • Children's Pool
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 19, 2018
    If you want a no-planning, no-hassle vacation in Costa Rica, this is for you. From the moment you arrive, EVERYTHING (food, laundry, planning the outings, transportation, etc...
    Reviewed April 10, 2017
    Our 12-year-old daughter was awarded a Make-a-Wish Foundation trip in late 2016, and spent the rest of the year trying to decide where to go. We were outwardly supportive of any...
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    About this property
    Words are hard to describe this property. It's a 3.5 acre beachfront property with three homes. Each home is privately secluded from the others, with trails and pathways full of colorful vegetation, connecting each home through-out the 3.5 acres. Our entrance is gated, and when you go through the...
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    Location Information
    Puerto Jimenez, Osa Peninsula CANAZA
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Ojo del Mar Ecolodge1 / 15
    (1)Excellent
    8 Bedrooms, 1 Bathroom, Sleeps 23 Quick View
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    • Shared Garden
    • Ocean Views
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 2017
    We just had the best time with Nico at Ojos de Mar. Wonderful jungle cabins are very clean and accommodating. Nico is a great cook and we really enjoyed ourselves in the main...
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    About this property
    Ojo del Mar ('eye of the sea'), is a small, eco friendly secluded retreat nestled between the pristine beaches and the tropical rainforest in the wilds of Costa Rica's Osa Peninsula. As National Geographic says, the Osa is the 'Last Great Peninsula,' still untouched by the ravages of civilization,...
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    Cabo Matapalo, Osa Peninsula 60702
    Holiday Rental House - 8 Bedrooms, 1 Bathroom, Sleeps 23
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    Beautiful home with pool in Golfito!!1 / 24
    (2)Very good
    2 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Patio
    • Grill
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Home!!! Fully equipped!! Two bedrooms available with bath and shower each one. All utilities include!! The owner lives on main floor, recently built and luxiourious.. Located in Golfito adjacent to four star hotel with fine dining and bar just steps away. Neighborhood is one of the...
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    Golfito, Osa Peninsula 60701
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 10
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    Casa Dulce - fabulous beachfront home located on Playa Pan Dulce, Cabo Matapalo1 / 14
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Internet Access
    • Parking
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 7, 2017
    Lovely house in a beautiful place! Not a luxury resort, but if you don't mind a little effort to get there and don't need to be waited on... Casa Dulce is a wonderful place to...
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    About this property
    Casa Dulce is a wonderful open air rancho located right on Playa Pan Dulce, which is one of the best sand beaches in the area. The location alone is reason to stay here, but couple the great location with the beautiful yard and pool and you're in for the trip of a lifetime! Pura Vida! Come visit....
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    Location Information
    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    200+AcreRainforest Estate/ Beaches/OZONE +4 Pools,PRIVATE MudSpa, Ocean View/LUX1 / 31
    (4)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Ocean Views
    • Housekeeping Included
    • Wi-Fi
    • Grill
    • Patio
    • Secure Parking
    • Private Indoor Pool
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 21, 2017
    We stayed at this rental home for 1 week, the last week of December into the first week of January. We had a group of 8 (four couples), and we had a great time. It was a...
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    About this property
    Corcovado's Osa Springs luxury retreat and vacation rental home is perfect for the discriminating vacationer who enjoys privacy and comfort. No other spa resort in Southern Costa Rica boasts this level of privacy, wildlife and luxury with exceptional accommodations and amenities overlooking the...
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    Location Information
    Puerto Jimenez, Osa Peninsula 00000
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    BookNowHUGE LUX Home/Beach/ SPAPool/Ocean View/Sleep12+/LOVE IT! GOTTA BOOK IT!1 / 35
    (24)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 17 Quick View
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    • Ocean Views
    • Hot Tub
    • Patio
    • Wi-Fi
    • Mountain Views
    • Grill
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 12, 2013
    Our group came to this incredible place at the end of the rainy season, and we were absolutely amazed. The house and pool, the jungle, the views of the golfo dulce, the birds...
    Reviewed June 22, 2012
    My husband and teenage kids stayed at the Lapa's home for 3 nights. This was the first stop to starting our vacation. We were looking for a private place that gave us the...
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    About this property
    You get the best of family vacations at Lapa’s Vacation Home Rental, where beach and rainforest collide on this private unique rainforest estate. Join the cacophony of wildlife and exotic birds that greet you each morning. Sombra de la Lapa Rainforest Reserve sits within 100’s of acres of private...
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    Puerto Jimenez, Osa Peninsula 00000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 17
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    HOT Deals  for Ultra COOL/4 BR/Private SPA/OzonePOOL/Ocean Views1 / 19
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Ocean Views
    • Mountain Views
    • Private Indoor Pool
    • Secure Parking
    • Wi-Fi
    • Housekeeping Included
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 21, 2017
    This is truly paradise. The accommodations were clean, spacious and very organized. Beds comfortable and due to the orientation of the property is was never too hot. The pool...
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    About this property
    Osa Springs- It’s almost like having a resort all to yourselves since this is a private rainforest estate.No need to decide if you want a Costa Rica beach house rental or rain forest rental - here at Osa Springs Luxury Resort -You get both! Complete and total privacy for rental guests is something...
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    Location Information
    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 9
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    200+ acre TREEHOUSE Rainforest Estate, Sleeps 2-8 / Ocean/Pool/King-Queen Beds.1 / 45
    (55)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Housekeeping Included
    • Waterfront
    • Mountain Views
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 17, 2018
    Staying in this deluxe Treehouse in the best part of Costa Rica to visit was a solid choice.The super friendly owners bent over backwards to accommodate and make our stay as...
    Reviewed February 27, 2016
    We are a group of 5 adults, well travelled in Central and South America, and have just returned from Michael and Blondie's amazing tree house. We surfed VRBO (HomeAway) looking...
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    About this property
    Voted Best Luxury Treehouse Estate in Costa Rica by TripAdvisor. Lapa’s Nest Treehouse vacation rental sleeps 8, with all amenities including screened rooms with reading lights and fans, comfy beds and imported sheets. Lapa’s Nest Treehouse Estate in Southern Costa Rica sits smack dab in middle of...
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    Osa Peninsula, Province of Puntarenas 00000
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new, stunning 3BR/3 full Bathroom townhome, beautifully decorated in 2014 by an international interior decorator – high quality (designer) furniture throughout is complemented by Feng Shui inspired colors and accessories to promote relaxation, peaceful tranquility and natural wellness, with a...
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    Location Information
    Cabo Matapalo, Osa Peninsula 50208
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Patio
    • Hot Tub
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is located in the gated community of Cabo Velas Estates, along with nine other condos allowing for privacy and tranquility. The large pool and rancho are ideal for community gathering and for entertaining. Relax in the hammock by the pool and enjoy the breeze and beautiful scenery while...
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    Location Information
    Cabo Matapalo, Osa Peninsula 50208
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cabo Matapalo Vacation Home, Osa Peninsula, Exotic Beaches, Primary Rainforest.1 / 23
    (22)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Washer
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 24, 2018
    We had a wonderfull time at tres Palmas with the whole family ( 12 adults and 7 kids aged between 1 and 10). It s quite an adventure to get there but the trip itself is worrh it...
    Reviewed May 17, 2017
    I have stayed in many luxurious places around the world - but nothing can compare to Tres Palmas. To begin with, we absolutely love the Osa Peninsula and have always stayed at...
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    About this property
    Enjoy the best of Costa Rica, at the beautiful Luxury Estate, Tres Palmas Costa Rica, boasting a Panoramic 180 degree view of the Pacific-Ocean, the Golfo Dulce and all the way to Panama, unlike none other. And nestled into the most lush animal filled jungle Primary Rainforest of the Osa Peninsula,...
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    Location Information
    Cabo Matapalo, Osa Peninsula 00000
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You’ll love my place because of Our cabins are good for couples, solo adventurers, and familys Enjoy a nice private jungle cabin in Cabo Matapalo. FULL KITCHEN, BBQ, POOL, and WIFI. Just steps away from many beautiful beaches and epic surf spots! One of the most biologically diverse places in the...
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    Location Information
    Cabo Matapalo, Osa Peninsula 92008
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Indoor Pool
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Fishack is a harborfront residential complex that includes three separate lodging options available either separately for small parties or together for groups. All are available for short-mid term rentals. The three-story home is situated on the edge of the Puerto Jimenez harbor and while...
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    Location Information
    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hotel de Montana El Tesoro de Sir
    7 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    • Ocean Views
    • Parking
    • Housekeeping Included
    • Mountain Views
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Drake Bay, Osa Peninsula 60530
    Condo/Apartment - 7 Bedrooms, 5 Bathrooms, Sleeps 24
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Children's Pool
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Playa Tortuga, Osa Peninsula 34949
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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