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Osa Peninsula Holiday Vacation with Pools

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    Travellers to Osa Peninsula are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    25 Matching Rentals in Osa PeninsulaView all 89 rentals
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Historic Golfito Luxury House1 / 40
    (7)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Beautiful Home with pool!!1 / 24
    (2)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    HOT Deals  for Ultra COOL/4 BR/Sleeps 9/POOL/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 21 July 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 reserve. 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 almost...
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    Puerto Jimenez, Osa Peninsula NO ZIPS EITHER
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 9
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    Cabo Matapalo Beach House  - 'Casa Verda'1 / 32
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Casa Verde (note misspelling on TripAdvisor) is the perfect place if you are looking for a quiet beach house at the end of the road. It is literally at the end of the last road...
    Reviewed 14 May 2017
    Last Easter, in April 2017 I had the opportunity to spend a few days of vacation in Casa Verde, in Cabo Matapalo, Osa Peninsula, Costa Rica.This gorgeous house is conveniently...
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    About this property
    Beautiful 'Open Air' two-story safari home with 3 private bedrooms that sleep 6. There are 2 hanging Hammocks in main central room for 2 additional guests if needed. Property is privately situated at the end of Matapalo Beach rd. on a pristine secluded beach surrounded by a tropical rain forest on...
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    Cabo Matapalo, Osa Peninsula 60602
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Manglar, Puerto Jimenez, OSA Peninsula1 / 55
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Patio
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 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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    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 7 March 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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    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, 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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    Osa Stardust1 / 11
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Mountain Views
    • Private Garden
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2017
    This place is awesome. We stayed here in the spring and our host, Peter, was great. He told us where to hike, eat, and what beaches were the best. He had a great recommendation...
    Reviewed 15 May 2017
    My husband and I arrived to Osa Stardust late into the evening, when it was very dark out. Peter, our host, was there waiting for us and showed us to the room. We could not see...
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    About this property
    Osa Stardust is a complete home in the hills overlooking the waters of the Golfo Dulce and the jungle canopy of the Osa Peninsula. The house has the privacy of a jungle retreat with a wraparound deck for sunning and bird watching. The sound of the surf on nearby beaches is the natural rhythm....
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    Puerto Jimenez, Osa Peninsula 60207
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Casaderodden1 / 95
    (11)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2017
    We stayed in Casa De Rodden in May of 2016. This is a beautiful home with Beautiful grounds. The owner, Edjuardo and his family were wonderful hosts. We could not have asked...
    Reviewed 9 January 2017
    We've now made two visits to CdR and the Osa Peninsula. Not only is the house (and the pool and the grounds and the facilities) great, the management -specifically Eduardo and...
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    About this property
    Full air conditioned house comes with fully equipped kitchen, laundry, living room areas, dinning areas, swimming pool, Jacuzzi, BBQ and pool bar outside, bar inside the house, ice machine, bar and kitchen refrigerators. There is maid service every day and permanent operations staff lives on the...
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    Location Information
    Puerto Jimenez, Osa Peninsula 506
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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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    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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    Location Information
    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 10 Bedrooms, 12 Bathrooms, Sleeps 30
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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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    Location Information
    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    The WHALE RESORT Puerto Jimenez Osa Peninsula1 / 58
    (9)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Air Conditioning
    • Children's Pool
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    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 10 April 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, 17 Bathrooms, 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 14 March 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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    Location Information
    Cabo Matapalo, Osa Peninsula 60702
    Holiday Rental House - 8 Bedrooms, 17 Bathrooms, Sleeps 23
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    Tres Palmas, Cabo Matapalo, Osa Peninsula1 / 23
    (20)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 17 May 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...
    Reviewed 10 April 2017
    This house or villa is outstanding for its workmanship, design, lay-out; spectacular view of the ocean, the pool is like a magnet, it draws you into itself.The staff was...
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    About this property
    Enjoy the highs of Costa Rica, at the beautiful hilltop Villa Tres Palmas, boasts a Panoramic 180 degree view of the Pacific-Ocean, the Golfo Dulce and all the way to Panama, unlike no other. And nestled into the most lush animal filled jungle rain-forest of the Osa Peninsula, and just steps...
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    Location Information
    Cabo Matapalo, Osa Peninsula 00000
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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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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    Mangrove Cabins at La Chosa del Manglar Nature Resort1 / 29
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • 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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    2 Bedrooms, 1 Bathroom, Sleeps 2 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
    Both Monkey Huts at Casa Manglar Guest House have a private bathroom with shower facility. They each have AC and one double bed. You are renting only one room. The bathrooms are located outside of the sleeping quarters. You are renting only one room not two. Casa Manglar is a stunning TROPICAL...
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    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • 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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    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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    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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    Location Information
    Drake Bay, Osa Peninsula 60530
    Condo/Apartment - 7 Bedrooms, 5 Bathrooms, Sleeps 24
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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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    Drake Bay, Osa Peninsula 12345
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Children's Pool
    • Hot Tub
    • Parking
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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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