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Holiday Rentals with Pools in Osa Peninsula

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    Travellers to Osa Peninsula are booking December dates now. Secure your holiday home today, and have the perfect trip.
    29 Matching Rentals in Osa PeninsulaView all 102 rentals
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    Casa Golfito with large private Pool1 / 22
    (11)Excellent
    4 Bedrooms, 4 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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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
    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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    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    The WHALE RESORT Puerto Jimenez Osa Peninsula1 / 58
    (13)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 29 July 2019
    The Whale Resort is simply amazing! From its team of people caring for you every day to its natural inhabitants to its accommodations for large groups, The Whale Resort more...
    Reviewed 11 March 2019
    We spent a week at the Whale Resort with our daughters, 11 and 13, and my parents, 68 years old. The property is great and we’re already missing the incredible view. By the...
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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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    Puerto Jimenez, Osa Peninsula CANAZA
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    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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    Puerto Jimenez, Osa Peninsula 60702
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Ocean Views
    • Wi-Fi
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Verde Find yourself in paradise at this two-story, open-air beach house. Enjoy ocean views in one direction and tropical rain forests in the other, all viewable from inside and outside this cozy getaway. This elevated, contemporary wood home features a wraparound, furnished lanai, a private,...
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    Cabo Matapalo, Osa Peninsula 00000
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    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
    Modern Beach House ☀️ Wifi ☀️ Pool ☀️ A/C1 / 27
    (26)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Patio
    • Porch
    • Wi-Fi
    • Secure Parking
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2019
    This beautiful house had tons of room for 5 of us. It's located close to a very nice beach and two resort restaurant/bars. It's only a 10 minute drive to town, and we were...
    Reviewed 5 June 2019
    The openness of the home is so inviting. Steps from the beach. Has all the amenities like in a hotel and more. Five of us were extremely comfortable in this modern sleek home...
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    About this property
    This newly renovated, large, three bedroom, 2 bathroom house with high ceilings and many lounging areas, makes for the perfect holiday beach rental house. Within 2 minutes walk from the house you will be on the most pristine palm lined, quiet beach in Costa Rica. It is hard to believe within this...
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    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Star Jungle Exp. - New Home, Private Pool, Beach1 / 17
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Washer
    • Outdoor Dining Area
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2019
    We loved everything about the house and the surroundings. High above Cabo Matapalo - amazing views - spectacular wildlife - perfect privacy. Couldn't have been any better! You...
    Reviewed 29 April 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...
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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
    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 21 January 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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    Puerto Jimenez, Osa Peninsula 00000
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    Cabo Matapalo, Osa Peninsula 50208
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Casa Vida Verde1 / 34
    (29)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Balcony
    • Patio
    • Wi-Fi
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 March 2016
    I was lucky enough to visit Casa Vida Verde this past February. The house is absolutely amazing. The location is so beautiful and the nearby beach was breathtaking.As i walked...
    Reviewed 20 February 2016
    Casa Vida Verde truly lives up to its name. The “Green Life” is omnipresent from its green cob construction, to its siting nestled in the jungle, with minimal disruption. No...
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    About this property
    This is the perfect location for an exotic honeymoon, a bird watching tour, a yoga retreat or a playful base for an unforgettable family vacation. Leave the real world behind and let your inner child emerge. The home is in Cabo Matapalo, on the Osa Peninsula in Costa Rica. With continuous...
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    Cabo Matapalo, Osa Peninsula 60702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • 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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    Cabo Matapalo, Osa Peninsula 50208
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 5
    Surfsidebungalows Casa Amarilla1 / 19
    (1)Excellent
    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
    Reviewed 15 March 2019
    So close to the surf, great kitchen and porch, and monkey visits on the reg !! Thank you Peter and we will be back.
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    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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    Cabo Matapalo, Osa Peninsula 92008
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Beautiful home with pool in Golfito!!1 / 33
    (2)Very good
    2 Bedrooms, 4 Bathrooms, Sleeps 6 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
    Newly built, ground floor level of private home for 6 people Includes full kitchen with granite countertops, large living room, dining room, 2 bedrooms, one bedroom has three queen size beds and private bath. The second bedroom is equipped with one doble size bed and two single beds, bathroom...
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    Golfito, Osa Peninsula 60701
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
    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 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 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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    Puerto Jimenez, Osa Peninsula 60702
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 9
    Cabo Matapalo Vacation Home, Osa Peninsula, Exotic Beaches, Primary Rainforest.1 / 23
    (23)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 5 days ago
    We had our destination wedding here in August 2019 and it was perfect. Ivan, the chef, took care of all the meals and wedding reception. Brad and Ivan literally made the week so...
    Reviewed 24 April 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...
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    About this property
    Enjoy the best of Costa Rica, at the beautiful Luxury Home, Tres Palmas Costa Rica, boasting a Panoramic 180 degree view of the Pacific-Ocean, the Golfo Dulce and all the way to Panama, unlike few others. And nestled into the most lush animal filled jungle Primary Rainforest of the Osa Peninsula,...
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    Cabo Matapalo, Osa Peninsula 00000
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
    Ojo del Mar Ecolodge1 / 15
    (2)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 24 January 2019
    Nico and staff have a lovely spot in the Osa along the beach. Tucked in the jungle, our stay was full of adventure of the Osa yet with the comfort of a nice resort. Nico's...
    Reviewed 15 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, 1 Bathroom, Sleeps 23
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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
    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
    2 Bedrooms, 4 Bathrooms, Sleeps 5 Quick View
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    • Private Indoor Pool
    • Parking
    • Private Garden
    • Mountain Views
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hummingbird House is perfect for 2 on vacation who want more privacy than others in this price range offer. Located on a 200+ acre private estate wildlife reserve, couples will enjoy total and complete privacy and quiet! It is the Illusion of Seclusion because it is only minutes from getting...
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    Corcovado National Park, Osa Peninsula 00000
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 5
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Villa features two levels built with post construction. The lower level is a large deck with an open air kitchen, and the upper level features a spacious room and balcony with great views. Constructed using eco-friendly recycled materials and reforested wood, it features both ocean and...
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    Location Information
    Drake Bay, Osa Peninsula 60504
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Waterfront
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will enjoy your stay in a rainforest gem located on 'The Promenade' in Puerto Jiménez. Our unique location gives us the best of both worlds with plenty of privacy from a canopy of almond and ficus trees while also being a short walk (2-3 minutes) from the best restaurants this quaint town has...
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    Puerto Jimenez, Osa Peninsula 60705
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Cable/satellite TV
    • Mountain Views
    • Housekeeping Included
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will enjoy your stay in a rainforest gem located on 'The Promenade' in Puerto Jiménez. Our unique location gives us the best of both worlds with plenty of privacy from a canopy of almond and ficus trees while also being a short walk (2-3 minutes) from the best restaurants this quaint town has...
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    Puerto Jimenez, Osa Peninsula 60705
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Ocean Views
    • Secure Parking
    • Washer
    • Wi-Fi
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    American Comfort with a Costa Rican flare! Close to many amenities, beaches short distance from house, Ocean Views, Shopping lots of wildlife for viewing, bird watching. Everything in a rental you could ever need we have thought of everything! Close to the towns of Ojochal, Uvita, Dominical and...
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    San Buena, Osa Peninsula 60015
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    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
    About this property
    Hotel Treasure Mountain Sir, back in the Treasury of Sir Francis Drake, because of the natural wealth of primary forest, flora and fauna. Located 5 km from the second largest Biological Station of Corcovado National Park: Plans. The Hotel is immersed between the primary forest, full of comfort and...
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    Drake Bay, Osa Peninsula 60530
    Condo/Apartment - 7 Bedrooms, 5 Bathrooms, Sleeps 24
    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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