Holiday rentals with a pool in Florida

Casa Anya @ Hilltop (private infinity plunge pool)

Imbuing Culebra’s magic with passionate India, Kavita’s native land, Casa Anya wraps you in contemporary airy spaces caressed by Indian linen. Savor bay and lush mountain vistas from a soothing rainfall grotto shower leading to a private plunge pool, and a full kitchen for romantic dining. Sliding doors to the deck invite in sunsets, stars, and enchanting breezes with chirping coquís. Fall into a king bed, and wake to pink dawns. Anya means grace in Hindi; let it grace your Caribbean dreams.

Esperanza Casita, Pool, Walk to Beach & Top Food

- Adults Only (18+) - Pool Hours 7am–7pm - Max 2 Adults (No Visitors) - Cold AC & Hot Water - New Queen Bed, TV, Microwave, Small Fridge - Beach Towels, Chairs, Snorkel Gear - No Tuesday Arrivals - 2-Night Min Fri & Sat - No Pets / No Smoking - Small Bags Recommended (Big Bags Fit Under Bed) - Quiet Hours: 10pm–6am Just 1.5 blocks from beaches, top restaurants & music. Relax after a day in the sun or enjoy a night out. For 20+ years, Coco Loco has been the choice for the perfect adult getaway.

Cielo Studio tranquility w/pool in rural location

The space is quiet and tucked away in the breezy hillside of Monte Carmelo. Rest your eyes on the views of the Caribbean, and rest your feet in the plunge pool. The plunge pool has great views for ultimate relaxation. Wifi throughout the property can also make the lounge chair swing, deck and pool areas productive as well. Monte Carmelo is a barrio that requires you to have your own transportation, and is centrally located between downtown Isabel and the ocean front restaurant row of Esperanza

Surf Side, Private Salt Water Pool, Ocean View

Across from the turquoise waters of the Atlantic Ocean and a short walk to La Chata Beach, you’ll find Surf Side House, with an expansive ocean view, and the main island of Puerto Rico and the sister island of Culebra as your backdrop. Located in Bravos de Boston on Vieques’ North Shore, this peaceful, private single family home features air conditioned bedroom with king size bed, two bathrooms with showers, one outdoor shower and a private heated salt water pool. Maximum occupancy 2 adults.

Magical! Ocean view Cabana w/ Pool Spa on mountain

This memorable place is anything but ordinary. You will get to enjoy this amazing and super private space surrounded by nature and unbelievable views of the ocean and the city. Fully equipped with everything you will need during your stay to include kitchen, full bath with rain shower, A/C, living space with 55" TV, dinning and sleeping areas, terrace with killer views, and of course the pool spa with infinity view! And many more. All of this while enjoying of a complementary bottle of Wine!

Casa Blanca with pool, tropical garden and rooftop

Experience a true authentic Caribbean vacation at our recently renovated home with a pool, rooftop and newly installed gorgeous tropical garden. Enjoy beautiful sunrise from the front of the house, the colorful sky during sunset hours from the rooftop and have a peaceful sleep with a subtle sound of the waves from the Atlantic ocean. Your family will be close to everything when you stay at this centrally-located place whether you are commuting from the airport, ferry terminal or Esperanza.

La Casita: Private Heated Pool W/ Ocean Views

Nestled atop a lush hill at the beachfront town of Ceiba, this 2-bedroom house is a haven of luxury & tranquility, offering a spectacular panoramic view of the ocean, the rainforest, mountains & neighboring islands. As you approach the property, a winding driveway bordered by vibrant, blooming flowers leads you to the entrance, setting the tone for the enchanting retreat that awaits. Just a 1-hour drive from SJU's International Airport & half hour ride from El Yunque National Rainforest.

Eco Hideaway with Ocean Views and Private Patio

This tropical hideaway, designed by acclaimed architect John Hix, is a tranquil oasis perched atop a breezy hill with breathtaking views of the Atlantic Ocean to the north and the Caribbean to the south. The loft features a private terrace, open-air shower, well-equipped kitchen, high thread count sheets, oversized plush towels, strong WiFi, and a uniquely beautiful shared pool. Despite the privacy of the property, Vieques' best beaches, restaurants, and trail heads are minutes away.

Casa Borinquen

This homey vacation rental is a brand new construction and is a great place to enjoy the outdoors. The interiors feature a modern design, a full kitchen, full bathroom, outdoor shower, and sleeps 3 people. Listen to the sound of the coquis at night and enjoy the tropical breve e, relaxing in the beautiful plunge pool or grilling on the outdoor deck, surrounded by lush palms, fruit trees (breadfruit, lemons, bananas, plantains, cashews), and herbs (mint, sweet peppers, oregano).