
Holiday houses in San Juan
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Top-rated holiday rentals in San Juan
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#4-New! Apartment, 1-BRoom, Kitchen, A/C, TV, Wifi
Welcome to: 🏡Roosevelt Guest House 🏝️🇵🇷 Tourism Department of PR 🇵🇷 Licence# 06/79/23-7781 🌳Very quiet lovely and peaceful 1 Bedroom apartments, 😴 , ♦️APARTMENTS ARE ALL INDEPENDENT, NOTHING SHARE ♦️ 10 minutes from SJU Airport✈️🛩, 10 minutes walking distance to Plaza las Americas, 5 minutes to El Coliseo de PR, 2-3 minutes Car driving to Plaza las Americas, 8-10 minutes to Condado Beach🏄🏽♀️🏝🏊🏼♂️, 12-15 minutes to Old San Juan, walking distance fasts foods restaurants , Bar’s and more.

Romantic Retreat~Walk Everywhere • Quiet & Central
Quiet, romantic retreat in the heart of Old San Juan—walk everywhere with ease & enjoy charm, comfort & restful sleep. ♥️ Tucked away from the street for peace & quiet ♥️ Steps to cafés, restaurants, nightlife & historic sites (Walk Score 98) ♥️ Comfortable Queen bed ♥️ Authentic Spanish Colonial charm ♥️ A/C, fast Wi-Fi + workspace ♥️ Fully equipped kitchen ♥️ Clean, stocked bathroom ♥️ Washer/dryer access ♥️ Live like a local in the heart of it all Perfect for couples—your quiet stay awaits.

El Secret Spot, a short walk to Isla Verde beach
Take it easy at this unique and tranquil getaway. A comfy, bohemian, chic, one bedroom apartment. Our one of a kind space offers a fully equipped kitchen, TV, WIFI, bbq, and a private backyard oasis surrounded by palm trees. Just a short walk to the Isla Verde beach and steps away from a local panadería and delightful coffee shop. At crossing the bridge you’ll find a world of restaurants, bars, clubs, and souvenir shops. We’re just a 5 min drive to the airport and 15 mins away from Old San Juan.

Design Villa w Garden & Jacuzzi | CASA FRIDA by DW
Fully restored Art Deco house in the historic Santurce neighborhood that boasts original creole tiles & geometric, stylized ornaments typical of its era. This short-term rental home mixes modern sensibilities to create a more streamlined, clean look. Look down to the bamboo garden from the roomy terrace while reclining in the hammock and dining alfresco. Built in the 40s, this upscale home features big walk-in rain showers, a hot tub, mid-century modern furniture, plus 2 terraces & 3 balconies.

#5 Boho Apt Studio: Close to beach/airport
Power Generator/ cistern. Steps from the beach yet away from crowds. Private entrance, art studio vibe. 4x6ft work table. No TV, calming atmosphere specially curated to foster relaxation. Natural light and large windows, creating an invigorating environment. The apartment has a unique history as the owner's personal sewing studio, adding a touch of artisanal spirit to the space. When not used for artistic pursuits, it becomes a welcoming retreat for travelers seeking solace and inspiration.

A Gem of a 2 bedroom condo unit close to the beach
This luxurious unit is located in a modern high rise building in an up and coming area in the isle of Old San Juan just one mile from the old Spanish town and near Condado. The location is perfect to access the famous beach of El Escambron (just 1 block away!) very popular among surfers. It´s a newly reformed gem of a condo unit loft-like style with exposed concrete ceilings and beams with floor to ceiling north looking windows in a corner unit with ample sun light all through the day-time.

⭐️Ocean View Apt. in Condado Beach & Strip⭐️
- 4min walk to beach - Located right on the strip - Just 10 minutes from the airport - Stylish, comfortable, and convenient open-layout apartment in San Juan's Condado Beach - Surrounded by vibrant cafes, top restaurants, and lively bars - Close to parks, Beaches, Placita Santurce, and Calle Loiza - Ideal for a couple or group of three - Seamless self-check-in for a hassle-free stay Immerse yourself in Puerto Rico's rich culture and charm. Book now and start your island adventure!

*Luxury PH-Apt* Best Location and Views* Wi-Fi,W/D
This PH unit have the best views of all San Juan from his spacious balcony, its located in La Placita area we’re all the bars, restaurants and night life are just a few steps away. The beach is just 10 mins walk and from (SJU) San Juan international airport it’s about 7-10 mins drive. The unit have Wi-fi and high speed internet and 2 T.V.s Free assigned parking in the same condo with control access. The Apt. is fully remodeled and equipped with all you will need to have a pleasant stay.

Walk 2 Beach! Gated prkg |Renovated! Bright & Cozy
Experience a cozy stay in our renovated 1-bedroom house, just a 5-minute walk to Ocean Park Beach and half a block from vibrant Calle Loíza. Enjoy free gated parking, a modern kitchen, washer-dryer, AC, ceiling fans, and a dedicated workspace. With two TVs, excellent internet, and beach essentials included, you'll have everything you need. Immerse in local culture and conveniently explore nearby attractions. If you don’t want to rent a car, you can easily walk or use Uber.

Classic Old San Juan; Best Location
Experience Old San Juan from this beautifully restored colonial-style building. Our cozy 2-bedroom apartment offers charm, comfort, and an unbeatable location—perfect for vacationing, a romantic getaway, a business trip, or a quick escape. Enjoy a spacious living room, a fully equipped kitchen, a comfortable bathroom, and a tranquil interior patio where you can relax and unwind. Book your stay today and make your visit truly unforgettable!

Casita del Sol☀️couples’ HOUSE-rooftop, water views
Casita del Sol offers a rare opportunity to rent an entire house in Old San Juan. Classic Spanish colonial architecture with multiple water views and huge rooftop deck. With an entirely removed secondary suite, it can be spacious enough for two couples or cozy enough for one. On a quiet and peaceful residential block, it is still just a short walk from the liveliest restaurants, bars, and shops and offers the best of life in Old San Juan.

ESJ, 10th Floor, Beach, Parking, 5 min SJU Airport
Million-dollar view—BOOK NOW! Proudly 100% Puerto Rican (and Veteran) owned. 🇵🇷 10th-floor studio w/ stunning sunsets. 5 min from SJU airport, <1 min walk from lobby to the beach! ✅ 1 free garage parking ✅ Self check-in ANYTIME after 3 PM ✅ Free luggage storage ✅ 24/7 market 10-min walk ✅ Lobby café & bar 🧺 Paid laundry in basement ❌ No pool ❌ No early check-in/out
Popular amenities for San Juan holiday rentals
Other great holiday rentals in San Juan

New Tropical Studio. Walking to the Beach & Rest.

Ocean View From Bed, Beach Access + Free Parking

⭐️Casa De Las Palmas 🌴🌴

Ocean-View Studio in Condado-Steps to the Beach!

Old San Juan Ocean View Historic House

En Casa de Tío

Luxury Marbella with Private Pool

Design Retreat w/ Stone Outdoor Shower – San Juan
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