Vacation rentals with a pool in Peninsula de Osa

Jaspis - Achiote Design Villas

Indulge in luxury in tasteful minimalist villa designed by the internationally awarded Formafatal studio. This place is like a consistent cocktail of top design and pure nature. Casa JASPIS offers one of the most beautiful ocean view in the whole area, which you can admire directly from the bed or from the terrace with private dip pool. Our unique place consist of 2 villas. Each villa has a private plunge infinity pool, large terrace and fully equipped kitchen with appliances by Kitchen Aid.

Value · Family · Decor

Finca Manglar-boat, horses, pool, tours included

FM is a private oasis that is perfect for adventurous families who want to explore the wonders of the Osa Peninsula. This luxury, rustic rainforest retreat allows you to escape from the hustle and bustle of everyday life and enjoy the peace and tranquility of nature. The property boasts spectacular gardens, abundant wildlife, and FREE guided tours, including fishing, beach visits, mangrove tours, tubing, horseback riding, kayaking, waterfall hikes, and relaxation by the indoor or outdoor pool.

Location · Value · Breakfast

Villa Kañik - Condé Nast Traveller Luxury Retreat

Villa Kañik is celebrated for its unique and sustainable architecture, winner of the Luxury Lifestyle Awards 2023 and recently featured by Condé Nast Traveller as one of the Best Places to Go in Central America in 2026. Immersed in the heart of one of Costa Rica’s most enchanting rainforests, where the jungle meets the sea, the villa offers breathtaking ocean views and the soothing sounds of tropical nature. Come experience why our Villa continues to capture the attention of world travellers.

Value · Location · Wifi

Award-Winning Eco-Luxury Retreat | Panoramic Views

Pura Vida Ecolodge: Award-winning eco-luxury sanctuary perched over the jungle canopy. Rated 5 stars for the "most breathtaking sunsets in CR" and "unbeatable ocean views"—perfect for romance & family adventures. 🌿 COSTA RICA'S GREEN SEASON: The rainforest is at its most vibrant! Experience lush waterfalls & wildlife. As 1% For the Planet members, your stay supports local conservation. Disconnect off-grid in our organic jungle nest. Book your sanctuary and experience the soul of Costa Rica.

Value · Family · Heating

Oasis on the beach| Private Pool | AC

Tucked away in the safe, idyllic tropical rainforest of Costa Rica’s South Pacific Coast, where lush green jungle meets the bright blue Pacific. One of the most biologically diverse regions on Earth, it’s home to Zancudo: a sleepy, off-the-beaten-path fishing village happily untouched by mass tourism. Zancudo delivers all the creature comforts, sodas, grocery shops, bars, local eateries, tours, and plenty to do - making it perfect for adventurers, digital nomads, couples, and families alike.

Family · Location · Kitchen

Luxury Eco Home with Modern Amenities and Pool

This comfortable beach home is in the desirable Matapalo area of the Osa peninsula and within a day trip to the Corcovado Nacional Park. The house is 150 m from the Playa Carbonera, a 15 minute beautiful walk to Playa Pan Dulce and a 10 minute drive to Playa Matapalo beach. The home is completely off the grid, generating its power from solar, and has many modern conveniences including full size fridge, industrial stove, solar hot water, wifi and a brand new dipping pool off of the deck.

Family · Location · Cleanliness

Casa Dulce - Great for small families or couples

Come to our beautiful vacation home Casa Dulce, a super cool open-air rancho located on Playa Pan Dulce (the best sand beach in the area) in Matapalo on the scenic Osa Peninsula. Enjoy our private two-acre preserve, bring your family, friends or that special someone to slow down, take your life at a different pace, and see how much clearer everything is when you step back into the peace, quiet and privacy of what feels like another world. Please read about the access to the upstairs loft.

Family · Value · Long stay

4bdr | 180° Ocean View House on a Mountain

4bd 2ba modern home - on the mountain, in a rain forest overlooking the ocean! Located high above Uvita, you'll feel disconnected from it all, yet only 12min from downtown & FAST wifi! The 180° views will stop you in your tracks. And of course there’s a pool to cool off in while enjoying a timeless vacation on a 66 acre oasis in the clouds. So whether it be a coffee or tea, a glass of wine, a cold drink it will pair perfectly with a Costa Rican sunset. 25$ per extra guest per night

Family · Value · Pool

Veranera: Pacific & spa in the heart of the jungle

Wake up facing the Pacific, in the heart of tropical nature. Designed for 2 people, Veranera offers a private terrace with spectacular ocean views, an air-conditioned bedroom, a fully equipped kitchen, and access to a spa nestled in the vegetation. On the estate: swimming pool, private waterfall, lookout point facing the Pacific, ranch, and 12,000 m² of nature where monkeys, toucans, coatis, and other wild animals can join the show. A true tropical retreat between jungle and ocean.

Location · Value · Backyard

Paradise Corcovado House

Elegant, with fine finishes, and spacious, this 3-bedroom house features AC, 2 bathrooms, a living room, kitchen, dining room, pool, and jacuzzi. Nestled amidst nature, it boasts incredible views of the Golfo Dulce and the Corcovado mountains, abundant bird and mammal wildlife, and complete privacy. Located 12 km from downtown Puerto Jiménez, our house has everything you need for an unforgettable stay. Breakfast is included in the price. 4x4 recommended, but not required.

Location · Hot tub · Laundry

Unique architecture. Beach & Jungle. Private Chef

Casa Atrevida is an architect-designed house with a contemporary look. It is both in the heart of the jungle and on a beautiful almost deserted beach. It offers five bedrooms (each with bathroom), an open living room, a large kitchen / dining room, a hanging garden and a pool. To make the most of this privileged environment, a team offers hotel services (private chef, security, concierge, daily cleaning...)

Location · Family · Shared spaces

Casa Amor:A Beautiful Accommodation Near the Ocean

Discover the charm of Casa Amor in the heart of Puerto Jiménez. Just a 3-minute walk from the main beach, this cozy property offers a refreshing shared pool and all the amenities to make you feel at home. Its excellent central location allows easy access to restaurants, supermarkets, and local services, ensuring a comfortable and memorable stay.

Location · Value · Quiet