
Holiday rentals with a pool in Osa
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Osa
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

2-BR Rainforest Villa w/ Pool & Ocean View
Casa Capung is nestled in the lush rainforest mountains of Costa Rica’s southern Pacific coast, conveniently located between Dominical and Uvita in the upscale area of Escaleras. This tropical-modern 2 bedroom 2 bath villa offers plenty of natural light, indoor/outdoor living space and views of both the jungle slopes and southern coastline. A perfect place for couples, honeymooners and families who desire relaxing in modern comforts with close proximity to beaches, waterfalls and town amenities.

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.

Private House & Pool - Whales Tail & Jungle Views
Escape to a tranquil 43-acre retreat in Costa Rica, approx. 1000 feet above sea level w/stunning Pacific Ocean & jungle views. Enjoy open indoor-outdoor living, jungle sounds, a pool for lounging. Accessible by 4x4, it’s near beaches, waterfalls, gyms, stores, banks and restaurants. The host greets guests at arrival and can arrange tours, check availability and make reservations, ensuring a seamless experience. Perfect for nature lovers seeking relaxation and adventure 🐒🦥🌸🌞🌴🦋 🦜

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.

Romantic Luxe Oceanview 5 Acre Estate - Concierge
You'll fall in love with Casa Mariposa's privacy, tranquility and fabulous Pacific Ocean and rainforest views. This elegant, luxurious, gated, comfortable house on 5.5 acres of rain forest is 700 feet above sea level in a quiet community near Parque National Marino Ballena. Close to dozens of restaurants, tours, shops and gorgeous beaches, a convenient 8 minute drive from the beach highway, 4x4's required. Message me to have our concierge arrange curated tours, private chef and spa services!

Tropical Spa - Ocean view - Asian Inspired
• No check out rules! • Pool+sauna+bathtub with ocean view • Back up system for up to 3 hrs • Indian Antique furniture and Balinese art • 180º ocean views from every room • Finished in August, 2022 • 2 levels: upstairs is the main residence (2b/2bth) and downstairs is studio-apartment with it's own laundry and kitchen • 7 minutes to the beach • Fully stocked and equipped kitchen • Napoleon Grill+wooden deck with sofa • Gate • AC in every bedroom and living room • Security cameras • Carport

Award Winning Pura Vida Ecolodge. Very Private
Beautiful & very private eco-luxury retreat near South Pacific Coast (4hr drive with 4WD car) from Juan Santamaria International Airport. Our unique & stunning location offers guests panoramic sea views & hangs dramatically over the jungle canopy. Romantic getaway, nature lovers & adrenalin junkies paradise! We’re proud to be a 1% For the Planet Member, giving 1% of our annual revenue back to local environmental nonprofits working on conservation projects for both our people and our planet.

Casa Palmeras Vista al Mar Casa Vacacional
Casa Palmeras es una casa nueva ubicada en las hermosas montañas de Playa Hermosa en la costa pacífica de Bahía Ballena en Costa Rica. Cuenta con dos habitaciones, un baño completo, cocina equipada, sala, comedor, terraza, hermosa piscina, ducha exterior, lavanderia, parqueo techado y un hermoso patio con áreas verdes. A tan solo 10 min manejando de Uvita y a 7 min manejando de Playa Hermosa. ¡Un lugar muy privado, acogedor y tranquilo para relajarse y disfrutar de la naturaleza!

Casa Selva - Jungle Escape
Welcome to Casa Selva, an architect-designed residence nestles in the heart of Ojochal's lush jungle. This stunning home offers an immersive tropical experience, surrounded by vibrant gardens, fruit trees, jungle, and frequent visits from monkeys, toucans, and many more of Costa Rica's natural wildlife species. Relax and unwind in the serence environment of Casa Selva. Take a dip in the refreshing pool. or indulge in the unique outdoor shower, feeling at one with nature.

Spectacular Ocean View Villa!
Talk about Location, Location, Location! Surfside Villa Dominicalito is uniquely located on a lush terraced hillside with a breathtaking 180 degree white wash view where you can watch the birds and monkeys all day. Surfside Villa Dominicalito is located inside the gated community of Canto del Mar (Song of the Sea) which many regard as the “best location in town.” It is a 10-minute walk to Playa Dominicalito and minutes from shopping, restaurants, and tourist attractions.

Luxury Studio with Private Pool
Disfruta de los sonidos de la naturaleza en este pequeño oasis situado solo metros del centro de Uvita, cerca de los mejores restaurantes de la zona, playas, cataratas, bancos, farmacia, supermercados y comercio en general. El espacio cuenta con tres Moderno Studios con un estilo único que están idealmente diseñadas para parejas. Cuenta con todas las comodidades necesarias para pasar unos días de relajo y disfrutar de las bondades naturales de la zona.

Casa Tres Arboles - Mountain- and Ocean-View
Casa Tres Arboles is the ideal place for couples and nature lovers. It is situated on a ridge above Uvita and combines the best and most beautiful of the region: You have a great view over the famous Whale Tail in the Pacific Ocean and can see with the naked eye every morning whether the tide allows an early visit to the beach or whether you should rather hike up the mountain. The pool is private. Pets are allowed. A 4x4 car is highly recommended.
Popular amenities for Osa rentals with a pool
House rentals with a pool

NEW! 360° Private Oasis• Ocean Views• By the Beach

Pura Uvita - Whale's tail ocean view, modern home

Casa Komorebi

Love Nest in Uvita | 180° Ocean Views

Hidden Villa Oasis with Panoramic Ocean Views

Casa Flores - luxury ocean view home

PRANA Entire House in Bahia, Uvita, Costa Rica.

Ocean view villa, big infinity pool
Condo rentals with a pool

Room 4 private apartment - Coliving Digital Nomads

Apartamento con piscina privada

IDEAL LIVING 1

Apt Sky blue

Villa Kila: Beach and Jungle 2 Bedroom Condo

SpectacularOceanViewJungle Condominium

Modern Couple’s Apartment Near Marino Ballena

Uvita - Moana Village V3 Studio
Other holiday rentals with a pool

Centrally Located Modern Home-AC & Pool!

Ocean View / Beach-Mountain Entreverde

Gema Escondida-Luxury and Private Villa

NEW! Mid-Century Luxury Casita Oceanview!

OCEAN VIEW WITH INFINITY POOL

Romantic Bali Casita, Private Pool, Wi-Fi

Villa Selva at Alma Tierra Mar

AIR@Mana Romantic Getaway*AC*Pvt Pool*Kitchen
Destinations to explore
- Smoking-friendly rentals Osa
- Rentals with a patio Osa
- Pet-friendly rentals Osa
- Hotel rentals Osa
- Beachfront rentals Osa
- Rentals with outdoor seating Osa
- Rentals with breakfast Osa
- Rentals with a washing machine and dryer Osa
- House rentals Osa
- Rentals with a fireplace Osa
- Nature eco lodge rentals Osa
- Rentals with a fire pit Osa
- Rentals with a kayak Osa
- Condo rentals Osa
- Waterfront rentals Osa
- Bed and breakfasts Osa
- Family-friendly rentals Osa
- Rentals with beach access Osa
- Apartment rentals Osa
- Rentals with a hot tub Osa
- Villa rentals Osa
- Bungalow rentals Osa
- Tiny house rentals Osa
- Guesthouse rentals Osa
- Cabin rentals Osa
- Boutique hotel rentals Osa
- Luxury rentals Osa
- Rentals with lake access Osa
- Rentals with pools Puntarenas
- Rentals with pools Costa Rica